Drug Reference for FDA Approved Psychiatric Drugs

Drug Reference for FDA Approved Psychiatric Drugs @ Neurotransmitter.net

Drugs for the following conditions are included: depression, anxiety disorders, bipolar disorder, schizophrenia, obsessive-compulsive disorder (OCD), attention-deficit hyperactivity disorder (ADHD), post-traumatic stress disorder (PTSD), panic disorder, and insomnia.
Many of the major metabolites listed are not active metabolites.
Off-label indications are not included.
The trade names of discontinued products are not mentioned.
This list only includes information about drugs which are available as tablets or capsules for oral consumption.
MDL Chime is required to view the "3D" chemical structures.
The possible mechanisms of action that I have suggested should be subjected to critical inquiry. Please consult PubMed, the PDSP K_i database, and the referenced literature to decide for yourself if my descriptions are accurate.
Some drugs described as inverse agonists may act as antagonists depending on the cell type and function considered. See Drug-Receptor Interactions by Rob Leurs for an introduction to concepts such as inverse agonism, partial agonism, and antagonism.
See Neurotransmitter.net's list of future treatments for depression, anxiety, sleep disorders, psychosis, and ADHD for information about psychiatric drugs in the FDA's clinical trials process.
Drug references for FDA approved general anesthetic drugs, FDA approved opioid painkillers, FDA approved epilepsy drugs, FDA approved Alzheimer's disease drugs, FDA Approved Parkinson's disease drugs, FDA approved migraine drugs, and FDA approved muscle relaxants and related drugs are also available.
E-mail Shawn Thomas if you have any suggestions about how this resource could be improved.
Updated 4/04/08
Types of Apothecary and Medicinal Glass Jars: Glass Apothecary Jars | Glass Jars | Glass Medicinal Jars

Generic Name: alprazolam Trade Name: Xanax ® [Pfizer] IUPAC Name: 8-chloro-6-cyclohexyl-1-methyl- 4H-[1,2,4]triazolo[4,3- a][1,4]benzodiazepine Dosage Forms/Routes: Tablet/oral; Tablet/orally disintegrating; Extended release tablet/oral; Concentrate/oral Major Metabolites: 4-hydroxyalprazolam; a-hydroxyalprazolam Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 10/16/1981 Manufacturers: [FDA Search] Product Insert: [Tablet] [XR Tablet] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₇H₁₃ClN₄ Molecular Mass: 308.765 g/mol	Indications: Anxiety disorder; Generalized Anxiety Disorder (GAD); panic disorder	Possible Mechanism of Action: Alprazolam is a nonselective benzodiazepine agonist (12).	Chemical Class: triazolo analog of the 1,4 benzodiazepine class PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: amitriptyline hydrochloride Common Chemical Name: 3-(10,11-dihydro-5H-dibenzo [a,d] cycloheptene-5- ylidene)-N,N-dimethyl-1- propanamine hydrochloride Dosage Forms/Routes: Tablet/oral Major Metabolites: nortriptyline; 10-hydroxyamitriptyline; 10-hydroxynortriptyline Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 04/07/1961 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₀H₂₄ClN Molecular Mass: 313.864 g/mol	Indications: Major Depressive Disorder	Possible Mechanisms of Action: Amitriptyline inhibits the reuptake of both serotonin and norepinephrine (1). Amitriptyline acts as an antagonist at all subtypes of muscarinic acetylcholine receptors (2). The drug also has antagonist activity at histamine H1 and H2 receptors, serotonin 5-HT2A receptors, and norepinephrine alpha-1 receptors (1). It also binds to histamine H4 receptors (11).	Chemical Class: tertiary tricyclic (dibenzocycloheptadine derivative) PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: amitriptyline hydrochloride and chlordiazepoxide Trade Name: Limbitrol ® [Valeant] Dosage Forms/Routes: Tablet/oral Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem]	Initial Approval: 12/23/1977 Manufacturers: [FDA Search] Product Insert: [Link] Epocrates: [Link] Empirical Formula: C₃₆H₃₇ClN₄O Molecular Mass: 613.619 g/mol	Indications: Moderate to severe depression associated with moderate to severe anxiety	Possible Mechanisms of Action: Please refer to the entries for amitriptyline hydrochloride and chlordiazepoxide.	PubChem 2D Structure:
Generic Name: amitriptyline hydrochloride and perphenazine Dosage Forms/Routes: Tablet/oral Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem]	Initial Approval: 08/23/1965 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₄₁H₅₀Cl₂N₄OS Molecular Mass: 717.833 g/mol	Indications: Treatment of patients with moderate to severe anxiety and/or agitation and depressed mood; patients with depression in whom anxiety and/or agitation are moderate or severe; patients with anxiety and depression associated with chronic physical disease; patients in whom depression and anxiety cannot be clearly differentiated; schizophrenic patients who have associated symptoms of depression	Possible Mechanisms of Action: Please refer to the entries for amitriptyline hydrochloride and perphenazine.	PubChem 2D Structure:
Generic Name: amoxapine Common Chemical Name: 2-chloro-11-(1-piperazinyldibenz- [b,f][1,4]oxapine Dosage Forms/Routes: Tablet/oral Major Metabolites: 8-hydroxyamoxapine; 7-hydroxyamoxapine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 09/22/1980 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₇H₁₆ClN₃O Molecular Mass: 313.781 g/mol	Indications: Depression in patients with neurotic or reactive depressive disorders as well as endogenous and psychotic depressions; depression accompanied by anxiety or agitation	Possible Mechanisms of Action: Amoxapine inhibits the reuptake of norepinephrine (5). The drug also inhibits glycine reuptake mediated by glycine transporter 2a (GLYT2a) (6). Amoxapine is an antagonist at serotonin 5-HT2A (7) and 5-HT2C receptors (7, 8). In addition, amoxapine is an antagonist at dopamine D2 receptors (9). It may also be an antagonist at alpha-1-adrenoceptors (130), histamine H1 receptors (130), and dopamine D4 receptors (9, 10). Finally, amoxapine binds with moderate affinity to alpha-2-adrenoceptors and binds with very low affinity to muscarinic acetylcholine receptors (131).	Chemical Class: tricyclic dibenzoxazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: aripiprazole Trade Name: Abilify ® [Bristol-Myers Squibb/Otsuka] IUPAC Name: 7-[4-[4-(2,3-dichlorophenyl) piperazin-1-yl]butoxy]-3,4- dihydro-1H-quinolin-2-one Dosage Forms/Routes: Tablet/oral; Solution/oral; Tablet/orally disintegrating; Injectable/intramuscular Major Metabolites: dehydro-aripiprazole Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 11/15/2002 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₃H₂₇Cl₂N₃O₂ Molecular Mass: 448.385 g/mol	Indications: Schizophrenia; acute manic and mixed episodes associated with bipolar disorder	Possible Mechanisms of Action: Depending on the cell type and function examined, aripiprazole is an agonist, partial agonist, or antagonist at dopamine D2 receptors (13). The drug is a partial agonist at dopamine D3 receptors (13). In addition, it is a partial agonist at serotonin 5-HT1A and 5-HT2A receptors and an inverse agonist at serotonin 5-HT2B receptors (13). Aripiprazole also exhibits significant affinity for serotonin 5-HT7 receptors, alpha-1A-adrenoceptors, and histamine H1 receptors (13).	PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: atomoxetine hydrochloride Trade Name: Strattera ® [Eli Lilly] IUPAC Name: N-methyl-3-(2-methylphenoxy)- 3-phenyl-propan-1-amine hydrochloride Dosage Forms/Routes: Capsule/oral Major Metabolites: 4-hydroxyatomoxetine; N-desmethylatomoxetine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 11/26/2002 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₇H₂₂ClNO Molecular Mass: 291.815 g/mol	Indications: ADHD	Possible Mechanisms of Action: Atomoxetine is a selective norepinephrine reuptake inhibitor (SNRI) (3). A major metabolite of atomoxetine, 4-hydroxyatomoxetine, is a partial agonist at kappa opioid receptors (4).	PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: bupropion hydrochloride Trade Name: Wellbutrin ®, Zyban® [GlaxoSmithKline] IUPAC Name: 1-(3-chlorophenyl)-2-tert- butylamino-propan-1-one hydrochloride Dosage Forms/Routes: Tablet/oral; Extended release tablet/oral Major Metabolites: hydroxybupropion; threohydrobupropion; erythrohydrobupropion Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/30/1985 Manufacturers: [FDA Search] Product Insert: [Tablet] [SR] [XL] [Zyban] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₃H₁₉Cl₂NO Molecular Mass: 276.202 g/mol	Indications: Major depressive disorder; smoking cessation aid	Possible Mechanisms of Action: Bupropion inhibits the norepinephrine and dopamine transporters with low potency (14). A metabolite of bupropion, hydroxybupropion, contributes to the drug's effects as a norepinephrine and dopamine reuptake inhibitor (14). The (2S,3S)- isomer of hydroxybupropion is a much more potent norepinephrine reuptake inhibitor than bupropion. Other bupropion metabolites may also contribute to the drug's effects at the norepinephrine and dopamine transporters (14). Bupropion is a noncompetitive antagonist at nicotinic acetylcholine receptors including the alpha3beta2, alpha4beta2, alpha3beta4, and alpha4beta4 subtypes (14, 15). Bupropion metabolites such as (2S,3S)-hydroxybupropion are also antagonists at nicotinic acetylcholine receptors (14).	Chemical Class: aminoketone PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: buspirone hydrochloride Trade Name: BuSpar ® [Bristol-Myers Squibb] IUPAC Name: 8-[4-(4-pyrimidin-2- ylpiperazin-1-yl)butyl]-8- azaspiro[4.5]decane-7,9- dione hydrochloride Dosage Forms/Routes: Tablet/oral Major Metabolites: 1-pyrimidinylpiperazine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 09/29/1986 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₁H₃₂ClN₅O₂ Molecular Mass: 421.964 g/mol	Indications: Anxiety disorders or short-term relief of the symptoms of anxiety	Possible Mechanisms of Action: Buspirone is a partial agonist at serotonin 5-HT1A receptors (17). It also acts as an antagonist at dopamine D2 receptors, but its affinity for these receptors is 16-fold weaker than its affinity for 5-HT1A receptors (18).	Chemical Class: piperazinyl derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: chlordiazepoxide hydrochloride Trade Name: Librium ® [Valeant] Common Chemical Name: 9-chloro-5-hydroxy-N-methyl- 6- phenyl-2,5- diazabicyclo[5.4.0]undeca- 1,6,8,10-tetraen-3-imine hydrochloride Dosage Forms/Routes: Capsule/oral Major Metabolites: desmethylchlordiazepoxide; demoxepam; desmethyldiazepam; oxazepam Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 02/24/1960 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₆H₁₅Cl₂N₃O Molecular Mass: 336.215 g/mol	Indications: Anxiety disorders or short-term relief of the symptoms of anxiety; withdrawal symptoms of acute alcoholism; preoperative apprehension and anxiety	Possible Mechanism of Action: Chlordiazepoxide is a nonselective benzodiazepine agonist (19, 20).	Chemical Class: 2-keto benzodiazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: chlorpromazine hydrochloride Trade Name: Thorazine ® [GlaxoSmithKline] IUPAC Name: 3-(2-chlorophenothiazin-10- yl)- N,N-dimethyl-propan-1- amine hydrochloride Dosage Forms/Routes: Tablet/oral; Injectable/injection; Syrup/oral; Concentrate/oral Major Metabolites: 7-hydroxychlorpromazine; 3-hydroxychlorpromazine; chlorpromazine N-oxide; chlorpromazine sulfoxide; norchlorpromazine; norchlorpromazine sulfoxide Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 11/20/1957 Manufacturers: [FDA Search] Product Insert: [Tablet] [Injectable] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₇H₁₉ClN₂S Molecular Mass: 318.865 g/mol	Indications: Schizophrenia; nausea and vomiting; relief of restlessness and apprehension before suregery; acute intermittent porphyria; adjunct in the treatment of tetanus; manic episodes associated with bipolar disorder; relief of intractable hiccups; for the treatment of severe behavioral problems in children (1 to 12 years of age) marked by combativeness and/or explosive hyperexcitable behavior (out of proportion to immediate provocations), and in the short-term treatment of hyperactive children who show excessive motor activity with accompanying conduct disorders consisting of some or all of the following symptoms: impulsivity, difficulty sustaining attention, aggressivity, mood lability and poor frustration tolerance	Possible Mechanisms of Action: Chlorpromazine is an antagonist at dopamine D1 and D2 receptors (21) as well as D3 (22) and D4 receptors (23). The drug may be an inverse agonist at dopamine D2S receptors (133). It also exhibits antagonist activity at serotonin 5-HT2A and 5-HT2C receptors (24). In addition, chlorpromazine is an antagonist at alpha-1A-adrenoceptors (25), alpha-1B-adrenoceptors (25), alpha-2B-adrenoceptors (26), alpha-2C-adrenoceptors (26), and histamine H1 receptors (27). The drug also binds with moderately high affinity to muscarinic M1, M3, M4, and M5 receptors (28). Finally, chlorpromazine binds with high affinity to serotonin 5-HT6 and 5-HT7 receptors (29).	Chemical Class: aliphatic phenothiazine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: citalopram hydrobromide Trade Name: Celexa ® [Forest Labs] IUPAC Name: 1-(3-dimethylaminopropyl)-1- (4-fluorophenyl)-3H- isobenzofuran-5-carbonitrile hydrobromide Dosage Forms/Routes: Tablet/oral; Tablet/orally disintegrating; Solution/oral Major Metabolites: demethylcitalopram; didemethylcitalopram; citalopram-N-oxide Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 07/17/1998 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₀H₂₂BrFN₂O Molecular Mass: 405.304 g/mol	Indications: Major depressive disorder	Possible Mechanism of Action: Citalopram is a selective serotonin reuptake inhibitor (SSRI) (16).	Chemical Class: racemic bicyclic phthalane derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: clomipramine hydrochloride Trade Name: Anafranil ® [Tyco Healthcare] Common Chemical Name: 3-chloro-5-[3- (dimethylamino)propyl]-10,11- dihydro-5H-dibenz[b,f]azepine monohydrochloride Dosage Forms/Routes: Capsule/oral Major Metabolites: desmethylclomipramine; 8-hydroxyclomipramine; 8-hydroxydesmethylclomipramine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/29/1989 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₉H₂₄Cl₂N₂ Molecular Mass: 351.313 g/mol	Indications: OCD in adults, children, and adolescents	Possible Mechanisms of Action: Clomipramine inhibits the reuptake of both serotonin and norepinephrine (30). The drug also binds to serotonin 5-HT2A, 5-HT2C, and 5-HT3 receptors, dopamine D2 and D3 receptors, and alpha-1-adrenoceptors (30). Clomipramine acts as an antagonist at muscarinic acetylcholine receptors (31), but the muscarinic receptor subtypes that it affects have not been identified. The drug is also an antagonist at histamine H1 receptors (32). Finally, clomipramine binds to serotonin 5-HT6 receptors (116).	Chemical Class: dibenzazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: clonazepam Trade Name: Klonopin ® [Roche] IUPAC Name: 6-(2-chlorophenyl)-9-nitro- 2,5-diazabicyclo[5.4.0]undeca- 5,8,10,12-tetraen-3-one Dosage Forms/Routes: Tablet/oral; Tablet/orally disintegrating Major Metabolite: 7-aminoclonazepam Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 06/04/1975 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₅H₁₀ClN₃O₃ Molecular Mass: 315.711 g/mol	Indications: Panic disorder; alone or as an adjunct in the treatment of the Lennox-Gastaut syndrome (petit mal variant), akinetic seizures, and myoclonic seizures; in patients with absence seizures (petit mal) who have failed to respond to succinimides, clonazepam may be useful	Possible Mechanism of Action: Clonazepam is a nonselective benzodiazepine agonist (12).	Chemical Class: 3-hydroxy benzodiazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: clorazepate dipotassium Trade Name: Tranxene ® [Ovation] IUPAC Name: dipotassium 9-chloro-3-oxo-6- phenyl-2,5- diazabicyclo[5.4.0]undeca- 5,8,10,12-tetraene-4-carboxylic acid hydroxide Dosage Forms/Routes: Tablet/oral; Capsule/oral Major Metabolites: nordiazepam; oxazepam Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 06/23/1972 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₆H₁₂ClK₂N₂O₄⁺ Molecular Mass: 409.927 g/mol	Indications: Anxiety disorders or short-term relief of the symptoms of anxiety; adjunctive therapy in the management of partial seizures; withdrawal symptoms of acute alcoholism	Possible Mechanism of Action: Clorazepate is a nonselective benzodiazepine agonist (33).	Chemical Class: 2-keto benzodiazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: clozapine Trade Name: Clozaril ® [Novartis] Common Chemical Name: 8-chloro-11-(4-methyl-1- piperazinyl)-5H-dibenzo [b,e] [1,4] diazepine Dosage Forms/Routes: Tablet/oral; Tablet/orally disintegrating Major Metabolite: N-desmethylclozapine; clozapine N-oxide Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 09/26/1989 Manufacturers: [FDA Search] Product Insert: [Clozaril tablet] [Orally disintegrating tablet] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₈H₁₉ClN₄ Molecular Mass: 326.823 g/mol	Indications: Treatment-resistant schizophrenia; reduction in the risk of recurrent suicidal behavior in schizophrenia or schizoaffective disorders	Possible Mechanisms of Action: Clozapine is a low affinity inverse agonist at dopamine D2S receptors (106, 133) and a high affinity antagonist at D4 receptors (34). It is also an antagonist at serotonin 5-HT2A (35), 5-HT2B (36), and 5-HT6 receptors (37). Clozapine is an inverse agonist at serotonin 5-HT2C (38) and 5-HT7 receptors (39). The drug is an antagonist at alpha-1A-adrenoceptors and alpha-1B-adrenoceptors (25). Clozapine is also an antagonist at alpha-2A-adrenoceptors and alpha-2C-adrenoceptors (40). Clozapine binds with relatively high affinity to alpha-2B-adrenoceptors (41); it likely acts as an antagonist at these receptors. Depending on cell type and receptor density, clozapine is an antagonist or partial agonist at muscarinic M1, M2, M3, and M4 receptors (42, 43). The drug is also an antagonist at muscarinic M5 receptors (44). Finally, clozapine is an antagonist at histamine H1 receptors (27).	Chemical Class: tricyclic dibenzodiazepine derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: desipramine hydrochloride Trade Name: Norpramin ® [Sanofi-Aventis] Common Chemical Name: 5 H -Dibenz[ bf ]azepine-5- propanamine, 10,11-dihydro- N-methyl-, monohydrochloride Dosage Forms/Routes: Tablet/oral Major Metabolite: 2-hydroxydesipramine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 11/20/1964 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₈H₂₃ClN₂ Molecular Mass: 302.841 g/mol	Indications: Various depressive syndromes, especially endogenous depression	Possible Mechanisms of Action: Desipramine is a high affinity norepinephrine reuptake inhibitor (45). It exhibits relatively low affinity for histamine H1 receptors, muscarinic acetylcholine receptors, and alpha-1-adrenoceptors (45).	Chemical Class: secondary tricyclic dibenzazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: desvenlafaxine succinate Trade Name: Pristiq ® [Wyeth] IUPAC Name: butanedioic acid; 4-[2-dimethylamino-1-(1- hydroxycyclohexyl)ethyl]phenol; hydrate Dosage Forms/Routes: Extended release tablet/oral Major Metabolite: desvenlafaxine glucoronide Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 02/29/2008 Manufacturers: [FDA Search] Product Insert: [Link] Empirical Formula: C₂₀H₃₃NO₇ Molecular Mass: 399.47852 g/mol	Indications: Major depressive disorder	Possible Mechanisms of Action: Desvenlafaxine inhibits the reuptake of serotonin and norepinephrine (154). It has a greater affinity for the serotonin transporter (154).	Chemical Class: the succinate salt of the isolated major active metabolite of venlafaxine, a phenethylamine bicyclic derivative PubChem 2D Structure:
Generic Name: dexmethylphenidate hydrochloride Trade Name: Focalin ® [Novartis] Common Chemical Name: alpha-phenyl-2-piperidineacetate hydrochloride, (R,R’)-(+)- Dosage Forms/Routes: Tablet/oral; Extended release capsule/oral Major Metabolite: d-ritalinic acid Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 11/13/2001 Manufacturers: [FDA Search] Product Insert: [Focalin Tablet] [Focalin XR Capsule] Epocrates: [Link] Empirical Formula: C₁₄H₁₉NO₂•HCl Molecular Mass: 269.77 g/mol	Indications: ADHD	Possible Mechanisms of Action: Dexmethylphenidate inhibits the dopamine transporter and, to a lesser degree, the norepinephrine transporter (46). The drug offers a better therapeutic index than racemic threo-methylphenidate hydrochloride (Ritalin®) (47).	Chemical Class: d-threo enantiomer of racemic methylphenidate hydrocholoride 2D Structure:
Generic Name: dextroamphetamine sulfate Trade Name: Dexedrine ® [GlaxoSmithKline] IUPAC Name: 1-phenylpropan-2-amine; sulfuric acid Dosage Forms/Routes: Tablet/oral; Extended release capsule/oral; Solution/oral Major Metabolites: p-hydroxyamphetamine; p-hydroxynorephedrine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 02/26/1976 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₈H₂₈N₂O₄S Molecular Mass: 368.492 g/mol	Indications: ADHD; narcolepsy Possible Mechanisms of Action: At plasmalemmal catecholamine transporters, amphetamine indirectly increases the efflux of cytosolic catecholamines so that they are released into the synaptic cleft (144). The drug causes the release of norepinephrine more potently than it causes the release of dopamine; it is much less effective as a serotonin releasing agent (144) The drug also directly inhibits norepinephrine and dopamine reuptake at higher concentrations (144). Amphetamine- induced activation of protein kinase C (PKC) beta(II) is likely to be responsible for the drug's effect on dopamine efflux (145). Na⁺ is cotransported with amphetamine as it enters neurons via catecholamine transporters; amphetamine-induced increases in intracellular Na⁺ may stimulate Na⁺/Ca²⁺ antiporters, resulting in an influx of Ca²⁺ into the cytosol (146). The activity of a Ca²⁺ dependent enzyme, phospholipase C (PLC), is increased by amphetamine, and PLC may be responsible for the increase in PKC beta(II) activity associated with amphetamine (146). Intracellular dopamine is also required for amphetamine- induced increases in PKC activity (146). Amphetamine increases the activity of phospholipase A2 (PLA2), perhaps by increasing intracellular pH (146). Low PLA2 activity may increase the activation of PKC, while high PLA2 activity may decrease the activation of PKC by amphetamine (146). Amphetamine, a weak base, increases cytosolic dopamine and norepinephrine through two mechanisms. First, amphetamine inhibits vesicular sequestration of dopamine and norepinephrine into vesicles by directly interacting with vesicular monoamine transporter-2 (VMAT-2) (147). Second, amphetamine decreases VMAT-2 activity by reducing the pH gradients that drive monoamine uptake into vesicles (148). At higher concentrations, amphetamine may act as a competitive antagonist at NMDA receptors (149). In addition, the drug is an agonist at TA1, a trace amine receptor (150).		Chemical Class: dextro isomer of d,l-amphetamine sulfate PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: diazepam Trade Name: Valium ® [Roche] IUPAC Name: 9-chloro-2-methyl-6-phenyl- 2,5-diazabicyclo[5.4.0]undeca- 5,8,10,12-tetraen-3-one Dosage Forms/Routes: Tablet/oral; Injectable/injection; Concentrate/oral; Gel/rectal Major Metabolites: nordiazepam; temazepam; oxazepam Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 11/15/1963 Manufacturers: [FDA Search] Product Insert: [Valium Tablet] [Injectable] [Gel] [Concentrate] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₆H₁₃ClN₂O Molecular Mass: 284.74 g/mol	Indications: Anxiety disorders or short-term relief of the symptoms of anxiety; symptomatic relief of acute alcohol withdrawal; adjunct for the relief of skeletal muscle spasm due to reflex spasm to local pathology, spasticity caused by upper motor neuron disorders, athetosis, and stiff-man syndrome; adjunct for convulsive disorders	Possible Mechanisms of Action: Diazepam is a nonselective benzodiazepine agonist (12). Diazepam is also an agonist at peripheral benzodiazepine receptors (48).	Chemical Class: 2-keto benzodiazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: divalproex sodium Trade Name: Depakote ® [Abbott Labs] IUPAC Name: sodium; 2-propylpentanoate; 2-propylpentanoic acid Dosage Forms/Routes: Tablet (delayed release)/oral; Capsule (delayed release pellets)/oral; Tablet (extended release)/oral Major Metabolites: 3-keto-valproic acid; trans-2-ene valproic acid; valproic acid glucuronide Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 03/10/1983 Manufacturers: [FDA Search] Product Insert: [Depakote Capsule] [Depakote Tablet] [Depakote ER Tablet] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₆H₃₁NaO₄ Molecular Mass: 310.405 g/mol	Indications: Depakote ER Only: Manic episodes associated with bipolar disorder; prophylaxis of migraine headaches All dosage forms: Monotherapy and adjunctive therapy in the treatment of patients with complex partial seizures that occur either in isolation or in association with other types of seizures; sole or adjunctive therapy in the treatment of simple and complex absence seizures; adjunct for the treatment of patients with multiple seizure types that include absence seizures	Possible Mechanisms of Action: Divalproex is a histone deacetylase inhibitor (49). The enhancement of gamma-aminobutyric acid (GABA) activity by divalproex is possibly due to the downregulation of GAT-1 and GAT-3 GABA transporter proteins by the drug (50); the cause of this effect is currently unknown. Divalproex also inhibits succinate semialdehyde dehydrogenase (153). At voltage-gated sodium channnels, divalproex shifts the voltage dependence of steady-state inactivation to more hyperpolarized potentials (51); the degree to which this action occurs at therapeutically relevant concentrations in humans is currently not known (52). Finally, divalproex may inhibit T-type calcium channels (53).	Chemical Class: carboxylic acid derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: doxepin hydrochloride Trade Name: Sinequan ® [Pfizer] Common Chemical Name: 1-Propanamine, 3- dibenz[b,e]oxepin- 11(6H)ylidene-N,N-dimethyl-, hydrochloride Dosage Forms/Routes: Capsule/oral; Concentrate/oral; Cream/topical Major Metabolite: desmethyldoxepin Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 09/23/1969 Manufacturers: [FDA Search] Product Insert: [Sinequan Capsule and Concentrate] [Zonalon Cream] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₉H₂₂ClNO Molecular Mass: 315.837 g/mol	Indications: Psychoneurotic patients with depression and/or anxiety; depression and/or anxiety associated with alcoholism (not to be taken concomitantly with alcohol); depression and/or anxiety associated with organic disease; psychotic depressive disorders with associated anxiety including involutional depression and bipolar disorders	Possible Mechanisms of Action: Doxepin weakly inhibits the reuptake of norepinephrine (54, 130) and serotonin (55, 130). It is a potent antagonist at histamine H1 (56, 57) and H2 receptors (57). Doxepin is also an antagonist at alpha-1-adrenoceptors (56). The drug binds to both serotonin 5-HT2A and 5-HT2C receptors (7). In addition, it is an antagonist at all subtypes of muscarinic acetylcholine receptors (58).	Chemical Class: dibenzoxepin derivative (tertiary tricyclic) PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: duloxetine hydrochloride Trade Name: Cymbalta ® [Eli Lilly] IUPAC Name: N-methyl-3-naphthalen-1- yloxy-3-thiophen-2-yl-propan- 1-amine hydrochloride Dosage Forms/Routes: Capsule, delayed release pellets/oral Major Metabolites: 4-hydroxy duloxetine glucuronide; 6-hydroxy-5-methoxy duloxetine glucoronide; 4, 6-dihydroxy duloxetine glucoronide; 5-hydroxy, 6-methoxy duloxetine sulfate Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 08/03/2004 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₈H₂₀ClNOS Molecular Mass: 333.876 g/mol	Indications: Major depressive disorder; diabetic peripheral neuropathic pain	Possible Mechanisms of Action: Duloxetine inhibits the reuptake of serotonin and norepinephrine (59).	Chemical Class: thiophenepropanamine PubChem 2D Structure:
Generic Name: escitalopram oxalate Trade Name: Lexapro ® [Forest Labs] IUPAC Name: 1-(3-dimethylaminopropyl)-1- (4- fluorophenyl)-1,3- dihydroisobenzofuran-5- carbonitrile; ethanedioic acid Dosage Forms/Routes: Tablet/oral; Capsule/oral; Solution/oral Major Metabolites: S-demethylcitalopram; S-didemethylcitalopram Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 08/14/2002 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₂H₂₃FN₂O₅ Molecular Mass: 414.427 g/mol	Indications: Major depressive disorder	Possible Mechanism of Action: Escitalopram is a selective serotonin reuptake inhibitor (SSRI) (45, 60).	Chemical Class: S-enantiomer of the racemic bicyclic phthalane derivative citalopram PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: estazolam Trade Name: Prosom ® [Abbott Labs] Common Chemical Name: 8-chloro-6-phenyl-4H-s- triazolo[4,3-a] [1,4]benzodiazepine Dosage Forms/Routes: Tablet/oral Major Metabolites: 1-oxo-estazolam; 4-hydroxy-estazolam Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/26/1990 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₆H₁₁ClN₄ Molecular Mass: 294.738 g/mol	Indications: Short-term treatment of insomnia	Possible Mechanism of Action: Estazolam is a nonselective benzodiazepine agonist (61).	Chemical Class: triazolobenzodiazepine derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: eszopiclone Trade Name: Lunesta ® [Sepracor] IUPAC Name: (7-oxo-2,5,8-triazabicyclo [4.3.0]nona-1,3,5- trien-9-yl) 2-(5-chloropyridin- 2-yl)-4-methyl-piperazine-1- carboxylate Dosage Forms/Routes: Tablet/oral Major Metabolites: (S)-zopiclone-N-oxide; (S)-N-desmethyl zopiclone Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/15/2004 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₇H₁₇ClN₆O₃ Molecular Mass: 388.808 g/mol	Indications: Treatment of insomnia	Possible Mechanisms of Action: Eszopiclone is the S-isomer and biologically active component of zopiclone. Zopiclone potentiates GABA-induced chloride currents in GABA-A receptors that contain the alpha-1 subunit or the combination of the beta2 subunit and the gamma2 subunit (62).	Chemical Class: pyrrolopyrazine derivative of the cyclopyrrolone class (S-isomer of zopiclone) PubChem 2D Structure:
Generic Name: fluoxetine hydrochloride Trade Name: Prozac ® [Eli Lilly] IUPAC Name: N-methyl-3-phenyl-3-[4- (trifluoromethyl)phenoxy]- propan-1-amine hydrochloride Dosage Forms/Routes: Tablet/oral; Capsule/oral; Solution/oral; Capsule, delayed release pellets/oral (weekly) Major Metabolite: norfluoxetine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/29/1987 Manufacturers: [FDA Search] Product Insert: [Prozac Capsule, Prozac Solution, and Prozac Weekly Capsule] [Fluoxetine Tablet] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₇H₁₉ClF₃NO Molecular Mass: 345.787 g/mol	Indications: Major depressive disorder in adults, children, and adolescents; OCD in adults, children, and adolescents; bulimia nervosa; panic disorder	Possible Mechanisms of Action: Fluoxetine inhibits the reuptake of serotonin (45). It is also an antagonist at serotonin 5-HT2C receptors (7, 63).	Chemical Class: bicyclic derivative of phenylpropylamine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: fluphenazine dihydrochloride IUPAC Name: 2-[4-[3-[2- (trifluoromethyl)phenothiazin- 10-yl]propyl]piperazin-1- yl]ethanol dihydrochloride Dosage Forms/Routes: Tablet/oral; Injectable/injection; Concentrate/oral; Elixir/oral Major Metabolites: 7-hydroxyfluphenazine; fluphenazine sulfoxide; fluphenazine N4-oxide Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 08/24/1960 Manufacturers: [FDA Search] Product Insert: [Tablet] [Injectable] [Concentrate] [Elixir] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₂H₂₈Cl₂F₃N₃OS Molecular Mass: 510.444 g/mol	Indications: Management of the manifestations of psychotic disorders	Possible Mechanisms of Action: Fluphenazine is an inverse agonist at dopamine D1 (64), D2 (27), D3 receptors (65), and D5 receptors (64, 66). Fluphenazine also binds with high affinity to dopamine D4 receptors (9). The drug is an antagonist at serotonin 5-HT2A receptors (24, 27). It has high affinities for serotonin 5-HT6 and 5-HT7 receptors (27, 29). In addition, fluphenazine is an antagonist at histamine H1 receptors (27). The drug also has high affinities for alpha-1A (27), alpha-1B (67), and alpha-2C-adrenoceptors (27).	Chemical Class: piperazine phenothiazine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: flurazepam dihydrochloride Trade Name: Dalmane ® [Valeant] IUPAC Name: 9-chloro-2-(2-diethylaminoethyl)- 6-(2-fluorophenyl)-2,5- diazabicyclo[5.4.0]undeca- 5,8,10,12-tetraen-3-one dihydrochloride Dosage Forms/Routes: Capsule/oral Major Metabolites: N-1-desalkylflurazepam; N-1-hydroxyethylflurazepam Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 04/07/1970 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₁H₂₅Cl₃FN₃O Molecular Mass: 460.799 g/mol	Indications: Short-term treatment of insomnia	Possible Mechanism of Action: Flurazepam is a nonselective benzodiazepine agonist (68).	Chemical Class: 2-keto benzodiazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: fluvoxamine maleate Trade Name: Luvox ® [Solvay] IUPAC Name: but-2-enedioic acid; 2-[5- methoxy-1-[4- (trifluoromethyl)phenyl]- pentylidene]aminooxyethanamine Dosage Forms/Routes: Tablet/oral; Extended release capsule/oral Major Metabolite: fluvoxamine acid Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/05/1994 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₉H₂₅F₃N₂O₆ Molecular Mass: 434.407 g/mol	Indications: OCD in adults, children, and adolescents	Possible Mechanisms of Action: Fluvoxamine is a serotonin reuptake inhibitor (69). It also acts as an agonist at sigma-1 receptors (70, 71).	PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: haloperidol lactate (also available as haloperidol or haloperidol decanoate) IUPAC Name: [4-(4-chlorophenyl)-1-[4-(4- fluorophenyl)-4-oxo-butyl]-4- piperidyl] 2-hydroxypropanoate Dosage Forms/Routes: Tablet/oral; Injectable/injection; Solution/oral; Concentrate/oral Major Metabolites: hydroxyhaloperidol (aka reduced haloperidol); haloperidol pyridinium; reduced haloperidol pyridinium; haloperidol tetrahydropyridine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 04/12/1967 Manufacturers: [FDA Search] Product Insert: [Tablet] [Injectable] [Solution] [Concentrate] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₁H₂₃ClFNO₂ Molecular Mass: 375.864 g/mol	Indications: Schizophrenia; control of tics and vocal utterances of Tourette's disorder	Possible Mechanisms of Action: Haloperidol is an inverse agonist at dopamine D1 (64), D2 (72), D3 (65, 73), and D5 receptors (64). The drug is an antagonist at dopamine D4 receptors (74). It binds with relatively low affinity to serotonin 5-HT2A receptors (27). Haloperidol is a partial agonist at alpha-1-adrenoceptors (75). It is also an antagonist at sigma-1 receptors and an agonist at sigma-2 receptors (76).	Chemical Class: butyrophenone PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: hydroxyzine dihydrochloride IUPAC Name: 2-[2-[4-[(4-chlorophenyl)- phenyl-methyl]piperazin-1- yl]ethoxy]ethanol dihydrochloride Dosage Forms/Routes: Tablet/oral; Capsule/oral; Syrup/oral; Injectable/injection; Suspension/oral Major Metabolite: cetirizine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 04/12/1956 Manufacturers: [FDA Search] Product Insert: [Tablet] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₁H₂₉Cl₃N₂O₂ Molecular Mass: 447.825 g/mol	Indications: For symptomatic relief of anxiety and tension associated with psychoneurosis and as an adjunct in organic disease states in which anxiety is manifested; management of pruritus due to allergic conditions such as chronic urticaria and atopic and contact dermatoses, and in histamine-mediated pruritus; as a sedative when used as pre-medication and following general anesthesia, hydroxyzine may potentiate meperidine and barbiturates, so their use in pre-anesthetic adjunctive therapy should be modified on an individual basis	Possible Mechanisms of Action: Hydroxyzine is a histamine H1 receptor antagonist (77). The drug also binds to sigma-1 receptors (78, 79). It may bind to serotonin 5-HT2A receptors as well (80).	Chemical Class: piperazine derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: hydroxyzine pamoate Trade Name: Vistaril ® [Pfizer] IUPAC Name: 4-[(3-carboxy-2-hydroxy- naphthalen-1-yl)methyl]-3- hydroxy-naphthalene- 2-carboxylic acid; 2-[2-[4-[(4- chlorophenyl)-phenyl- methyl]piperazin-1- yl]ethoxy]ethanol Dosage Forms/Routes: Capsule/oral Major Metabolite: cetirizine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 11/15/1968 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₄₄H₄₃ClN₂O₈ Molecular Mass: 763.274 g/mol	Indications: For symptomatic relief of anxiety and tension associated with psychoneurosis and as an adjunct in organic disease states in which anxiety is manifested; management of pruritus due to allergic conditions such as chronic urticaria and atopic and contact dermatoses, and in histamine-mediated pruritus; as a sedative when used as pre-medication and following general anesthesia, hydroxyzine may potentiate meperidine and barbiturates, so their use in pre-anesthetic adjunctive therapy should be modified on an individual basis	Possible Mechanisms of Action: Hydroxyzine is a histamine H1 receptor antagonist (77). The drug also binds to sigma-1 receptors (78, 79). It may bind to serotonin 5-HT2A receptors as well (80).	Chemical Class: piperazine derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: imipramine hydrochloride Trade Name: Tofranil ® [Tyco Healthcare] Common Chemical Name: 5-[3-(dimethylamino)propyl]- 10,11-dihydro-5H-dibenz [b,f]azepine monohydrochloride Dosage Forms/Routes: Tablet/oral Major Metabolite: desipramine (aka desmethylimipramine); 2-hydroximipramine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 10/02/1959 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₉H₂₅ClN₂ Molecular Mass: 316.868 g/mol	Indications: Major depressive disorder, especially endogenous depression; childhood enuresis	Possible Mechanisms of Action: Imipramine inhibits the reuptake of serotonin and norepinephrine (81). It is an antagonist at histamine H1 and alpha-1-adrenoceptors (82, 130). In addition, the drug is an antagonist at M2 muscarinic acetylcholine receptors (83).	Chemical Class: tertiary dibenzazepine tricyclic PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: imipramine pamoate Trade Name: Tofranil-PM ® [Tyco Healthcare] Common Chemical Name: 5-[3-(dimethylamino)propyl]- 10,11-dihydro-5H- dibenz[b,f]azepine 4, 4'- methylenebis-(3-hydroxy- 2-naphthoate) (2:1) Dosage Forms/Routes: Capsule/oral Major Metabolite: desipramine (aka desmethylimipramine); 2-hydroximipramine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 03/11/1973 Manufacturers: [FDA Search] Product Insert: [Link] Epocrates: [Link] Empirical Formula: C₆₁H₆₄N₄O₆ Molecular Mass: 949.184 g/mol	Indications: Major depressive disorder, especially endogenous depression	Possible Mechanisms of Action: Imipramine inhibits the reuptake of serotonin and norepinephrine (81). Imipramine binds to both histamine H1 and alpha-1-adrenoceptors (82). In addition, the drug is an antagonist at M2 muscarinic acetylcholine receptors (83).	Chemical Class: tertiary dibenzazepine tricyclic PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: isocarboxazid Trade Name: Marplan ® [Oxford] IUPAC Name: N-benzylamino-5-methyl- oxazole-3-carboxamide Dosage Forms/Routes: Tablet/oral Major Metabolite: benzylhydrazine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 07/01/1959 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₂H₁₃N₃O₂ Molecular Mass: 231.251 g/mol	Indications: Major depressive disorder	Possible Mechanisms of Action: Isocarboxazid is an irreversible inhibitor of monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B) (84).	Chemical Class: hydrazine derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: lamotrigine Trade Name: Lamictal ® [GlaxoSmithKline] IUPAC Name: 6-(2,3-dichlorophenyl)-1,2,4- triazine-3,5-diamine Dosage Forms/Routes: Tablet/oral; Chewable Tablet/oral Major Metabolite: lamotrigine 2-N-glucuronide Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/27/1994 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₉H₇Cl₂N₅ Molecular Mass: 256.091 g/mol	Indications: The maintenance treatment of bipolar I disorder to delay the time to occurrence of mood episodes (depression, mania, hypomania, mixed episodes) in patients treated for acute mood episodes with standard therapy; adjunctive therapy for partial seizures in adults and pediatric patients (>/= 2 years of age); adjunctive therapy for the generalized seizures of Lennox-Gastaut syndrome in adult and pediatric patients (>/= 2 years of age)	Possible Mechanisms of Action: Lamotrigine blocks voltage-gated sodium channels in a use-dependent manner (85). The drug preferentially binds to the channel pore in inactivated but not resting sodium channels; its inhibition of sodium channels is therefore increased by neuronal depolarization (86). Lamotrigine also inhibits N-type and P/Q-type voltage-gated calcium channels (87, 88).	Chemical Class: phenyltriazine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: lisdexamfetamine dimesylate Trade Name: Vyvanse ® [Shire] IUPAC Name: (2S)-2,6-diamino-N-[(2S)-1-phenylpropan- 2-yl]hexanamide; methanesulfonic acid Dosage Forms/Routes: Capsule/oral Major Metabolites: p-hydroxyamphetamine; p-hydroxynorephedrine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 02/23/2007 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₇H₃₃N₃O₇S₂ Molecular Mass: 455.58982 g/mol	Indications: ADHD	Possible Mechanisms of Action: Vyvanse is a prodrug of dextroamphetamine. After oral administration, lisdexamfetamine dimesylate is rapidly absorbed from the gastrointestinal tract and converted to dextroamphetamine, which is responsible for the drug's activity.	Chemical Class: prodrug of the dextro isomer of d,l-amphetamine sulfate PubChem 2D Structure:
Generic Name: lithium carbonate Trade Name: Eskalith ® [GlaxoSmithKline] IUPAC Name: dilithium carbonate Dosage Forms/Routes: Tablet/oral; Capsule/oral; Extended release tablet/oral Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 04/06/1970 Manufacturers: [FDA Search] Product Insert: [Tablet/Capsule] [Extended Release Capsule] RxList: [Link] Epocrates: [Link] Empirical Formula: CLi₂O₃ Molecular Mass: 73.8909 g/mol	Indications: Manic episodes associated with bipolar disorder or maintenance treatment for individuals with bipolar disorder	Possible Mechanisms of Action: Please consult PubMed; the mechanisms of action of lithium are too complex to properly explain here.	PubChem 2D Structure:
Generic Name: lithium citrate IUPAC Name: trilithium 2-hydroxypropane-1,2,3- tricarboxylate Dosage Forms/Routes: Syrup/oral Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 04/06/1970 Manufacturers: [FDA Search] Product Insert: [Link] (syrup) RxList: [Link] Epocrates: [Link] Empirical Formula: C₆H₅Li₃O₇ Molecular Mass: 209.9227 g/mol	Indications: Manic episodes associated with bipolar disorder or maintenance treatment for individuals with bipolar disorder	Possible Mechanisms of Action: Please consult PubMed; the mechanisms of action of lithium are too complex to properly explain here.	PubChem 2D Structure:
Generic Name: lorazepam Trade Name: Ativan ® [Biovail] IUPAC Name: 9-chloro-6-(2-chlorophenyl)-4- hydroxy-2,5- diazabicyclo[5.4.0]undeca- 5,8,10,12-tetraen-3-one Dosage Forms/Routes: Tablet/oral; Injectable/injection; Solution/oral; Concentrate/oral Major Metabolite: lorazepam glucuronide Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 09/30/1977 Manufacturers: [FDA Search] Product Insert: [Tablet] [Injectable] [Lorazepam Intensol Concentrate] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₅H₁₀Cl₂N₂O₂ Molecular Mass: 321.158 g/mol	Indications: Anxiety disorders or short-term relief of the symptoms of anxiety or anxiety associated with depressive symptoms	Possible Mechanism of Action: Lorazepam is a nonselective benzodiazepine agonist (12).	Chemical Class: 3-hydroxy benzodiazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: loxapine succinate Trade Name: Loxitane ® [Watson] Common Chemical Name: 2-chloro-11-(4-methyl-1- piperazinyl)dibenz[b,f][1,4] oxazepine Dosage Forms/Routes: Capsule/oral Major Metabolites: 8-hydroxyloxapine; 7-hydroxyloxapine; 8-hydroxyamoxapine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 02/25/1975 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₂H₂₄ClN₃O₅ Molecular Mass: 445.896 g/mol	Indications: Schizophrenia	Possible Mechanisms of Action: Loxapine is an antagonist at dopamine D1 (89), D2 (90), and D3 receptors (91). The drug also binds to D4 and D5 receptors (67). It is an antagonist at serotonin 5-HT2A receptors (92) and an inverse agonist at 5-HT2C receptors (38). In addition, the drug has been found to bind to serotonin 5-HT6 receptors (27). It also binds with low affinity to 5-HT7 receptors (27). Additional binding sites of loxapine include alpha-1A-adrenoceptors, alpha-1B-adrenoceptors, and histamine H1 receptors (67).	Chemical Class: tricyclic dibenzoxazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: maprotiline hydrochloride Major Metabolites: desmethylmaprotiline; maprotiline N-oxide Dosage Forms/Routes: Tablet/oral Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/01/1980 Manufacturers: [FDA Search] Product Insert: [Link] Epocrates: [Link] Empirical Formula: C₂₀H₂₄ClN Molecular Mass: 313.864 g/mol	Indications: Major Depressive Disorder	Possible Mechanisms of Action: Maprotiline is a norepinephrine reuptake inhibitor (93). It is also a potent histamine H1 receptor antagonist (94). The drug may act as an antagonist at some muscarinic acetylcholine receptor subtypes (95, 96). Maprotiline is also a weak to moderate affinity antagonist of alpha-1-adrenoceptors (130).	Chemical Class: tetracyclic PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: meprobamate IUPAC Name: [2-(carbamoyloxymethyl)-2- methyl-pentyl] aminoformate Dosage Forms/Routes: Tablet/oral Major Metabolite: 2-hydroxymeprobamate; meprobamate glucuronide; meprobamate glucosyluronide Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 04/28/1955 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₉H₁₈N₂O₄ Molecular Mass: 218.25 g/mol	Indications: Anxiety disorders or short-term relief of the symptoms of anxiety	Possible Mechanism of Action: Meprobamate is a barbiturate-like positive modulator of GABA-A receptor complexes (97).	Chemical Class: propanediol dicarbamate PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: methamphetamine hydrochloride Trade Name: Desoxyn ® [Ovation] IUPAC Name: N-methyl-1-phenyl-propan-2- amine hydrochloride Dosage Forms/Routes: Tablet/oral Major Metabolite: amphetamine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/31/1943 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₀H₁₆ClN Molecular Mass: 185.693 g/mol	Indications: ADHD	Possible Mechanism of Action: Please consult PubMed; the mechanisms of action of methamphetamine are too complex to properly explain here.	Chemical Class: amphetamine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: methylphenidate transdermal system Trade Name: Daytrana ® [Shire] IUPAC Name: methyl 2-phenyl-2-(2- piperidyl)acetate Dosage Forms/Routes: Extended release film; transdermal Major Metabolite: dl-ritalinic acid Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 4/06/2006 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Empirical Formula: C₁₄H₁₉NO₂ Molecular Mass: 233.306 g/mol	Indications: ADHD	Possible Mechanisms of Action: Methylphenidate inhibits the reuptake of dopamine and norepinephrine (3). The drug has a higher affinity (~ 10-fold) for dopamine transporters than norepinephrine transporters (3).	Chemical Class: piperidine derivative in a multipolymeric adhesive PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: methylphenidate hydrochloride Trade Name: Ritalin ® [Novartis]; Concerta ® [Alza] IUPAC Name: methyl 2-phenyl-2-(2- piperidyl)acetate hydrochloride Dosage Forms/Routes: Tablet/oral; Chewable tablet/oral; Extended release tablet/oral; Extended release capsule/oral; Solution/oral Major Metabolite: dl-ritalinic acid Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/05/1955 Manufacturers: [FDA Search] Product Insert: [Tablet - Ritalin] [Extended Release Capsule - Ritalin LA] [Extended Release Tablet - Concerta] RxList: [Link] Epocrates: [Link] [Link 2] (Concerta) Empirical Formula: C₁₄H₂₀ClNO₂ Molecular Mass: 269.767 g/mol	Indications: ADHD, narcolepsy	Possible Mechanisms of Action: Methylphenidate inhibits the reuptake of dopamine and norepinephrine (3). The drug has a higher affinity (~ 10-fold) for dopamine transporters than norepinephrine transporters (3).	Chemical Class: piperidine derivative (a 50:50 mixture of racemic threo-methylphenidate hydrochloride) PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: mirtazapine Trade Name: Remeron ® [Organon] Common Chemical Name: 1,2,3,4,10,14b-hexahydro-2- methylpyrazino [2,1-a] pyrido [2,3-c] benzazepine Dosage Forms/Routes: Tablet/oral; Tablet/orally disintegrating Major Metabolite: desmethylmirtazapine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 06/14/1996 Manufacturers: [FDA Search] Product Insert: [Tablet] [Orally Disintegrating Tablet] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₇H₁₉N₃ Molecular Mass: 265.353 g/mol	Indications: Major depressive disorder	Possible Mechanisms of Action: Mirtazapine is an antagonist at serotonin 5-HT2A, 5-HT2C, and 5-HT3 receptors (98). Mirtazapine is also an antagonist at alpha-2-adrenoceptors and histamine H1 receptors (98).	Chemical Class: tetracyclic piperazinoazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: mixed amphetamine salts Trade Name: Adderall ® [Shire] Drug Constituents: dextroamphetamine saccharate; d,l-amphetamine aspartate monohydrate; dextroamphetamine sulfate; d,l-amphetamine sulfate Dosage Forms/Routes: Tablet/oral; Extended release capsule/oral Major Metabolite: p-hydroxyamphetamine; p-hydroxynorephedrine; norephedrine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 01/19/1960 Manufacturers: [FDA Search] Product Insert: [Tablet] [Extended Release Capsule] RxList: [Link 1] [Link 2] (XR) Epocrates: [Link]	Indications: ADHD Possible Mechanisms of Action: At plasmalemmal catecholamine transporters, amphetamine indirectly increases the efflux of cytosolic catecholamines so that they are released into the synaptic cleft (144). The drug causes the release of norepinephrine more potently than it causes the release of dopamine; it is much less effective as a serotonin releasing agent (144) The drug also directly inhibits norepinephrine and dopamine reuptake at higher concentrations (144). Amphetamine- induced activation of protein kinase C (PKC) beta(II) is responsible for the drug's effect on dopamine efflux (145). Na⁺ is cotransported with amphetamine as it enters neurons via catecholamine transporters; amphetamine-induced increases in intracellular Na⁺ may stimulate Na⁺/Ca²⁺ antiporters, resulting in an influx of Ca²⁺ into the cytosol (146). The activity of a Ca²⁺ dependent enzyme, phospholipase C (PLC), is increased by amphetamine, and PLC may be responsible for the increase in PKC beta(II) activity associated with amphetamine (146). Intracellular dopamine is also required for amphetamine- induced increases in PKC activity (146). Amphetamine increases the activity of phospholipase A2 (PLA2), perhaps by increasing intracellular pH (146). Low PLA2 activity may increase the activation of PKC, while high PLA2 activity may decrease the activation of PKC by amphetamine (146). Amphetamine, a weak base, increases cytosolic dopamine and norepinephrine through two mechanisms. First, amphetamine inhibits vesicular sequestration of dopamine and norepinephrine into vesicles by directly interacting with vesicular monoamine transporter-2 (VMAT-2) (147). Second, amphetamine decreases VMAT-2 activity by reducing the pH gradients that drive monoamine uptake into vesicles (148). At higher concentrations, amphetamine may act as a competitive antagonist at NMDA receptors (149). In addition, the drug is an agonist at TA1, a trace amine receptor (150).		Chemical Class: amphetamine
Generic Name: molindone hydrochloride Trade Name: Moban ® [Endo] IUPAC Name: 3-ethyl-2-methyl-5-(1-oxa-4- azoniacyclohex-4-ylmethyl)- 1,5,6,7-tetrahydroindol-4-one chloride Dosage Forms/Routes: Tablet/oral Major Metabolites: Not known Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 01/18/1974 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₆H₂₅ClN₂O₂ Molecular Mass: 312.835 g/mol	Indications: Schizophrenia	Possible Mechanisms of Action: Molindone is an antagonist at dopamine D2 and D3 receptors (10). An unidentified metabolite of molindone may irreversibly inhibit monoamine oxidase A (151, 152).	Chemical Class: dihydroindolone PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: nefazodone hydrochloride IUPAC Name: 2-[3-[4-(3- chlorophenyl)piperazin-1- yl]propyl]-5-ethyl-4-(2- phenoxyethyl)-1,2,4-triazol-3- one hydrochloride Dosage Forms/Routes: Tablet/oral Major Metabolites: hydroxynefazodone; triazoledione; m-chlorophenylpiperazine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/22/1994 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₅H₃₃Cl₂N₅O₂ Molecular Mass: 506.467 g/mol	Indications: Major depressive disorder	Possible Mechanisms of Action: Nefazodone is an antagonist at serotonin 5-HT2A receptors (99). It weakly inhibits serotonin and norepinephrine reuptake (99). Nefazodone is an antagonist at histamine H1 receptors and alpha-1-adrenoceptors (45). The drug also binds to 5-HT1A receptors (45, 82) and alpha-2-adrenoceptors (45).	Chemical Class: phenylpiperazine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: nortriptyline hydrochloride Trade Name: Pamelor ® [Tyco Healthcare] Common Chemical Name: 1-Propanamine, 3-(10,11- dihydro, 5H-dibenzo [a, d] cyclohepten-5-ylidene)-N- methyl-,hydrochloride Dosage Forms/Routes: Capsule/oral; Solution/oral Major Metabolite: 10-hydroxynortriptyline Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 11/06/1964 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₉H₂₂ClN Molecular Mass: 299.837 g/mol	Indications: Major depressive disorder, especially endogenous depression	Possible Mechanisms of Action: Nortriptyline inhibits the reuptake of norepinephrine (100). At serotonin 5-HT2A receptors, nortriptyline is an antagonist (101). The drug is also a low potency antagonist at histamine H1 receptors (102) and some subtypes of muscarinic acetylcholine receptors (103).	Chemical Class: dibenzocycloheptadiene (tricyclic) PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: olanzapine Trade Name: Zyprexa ® [Eli Lilly] Common Chemical Name: 2-methyl-4-(4-methyl-1- piperazinyl)-10H-thieno[2,3-b] [1,5]benzodiazepine Dosage Forms/Routes: Tablet/oral; Injectable/intramuscular; Tablet/orally disintegrating Major Metabolites: olanzapine 10-N-glucuronide; olanzapine 4'-N-glucuronide; 4'-N-desmethylolanzapine; olanzapine N-oxide Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 09/30/1996 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₇H₂₀N₄S Molecular Mass: 312.434 g/mol	Indications: Schizophrenia; acute monotherapy of acute mixed or manic episodes associated with bipolar I disorder; maintenance monotherapy of bipolar patients; combination with lithium or valproate for the short-term treatment of manic episodes associated with bipolar I disorder; Zyprexa intramuscular is indicated for the treatment of agitation associated with schizophrenia and bipolar I mania	Possible Mechanisms of Action: Olanzapine is a low potency antagonist at dopamine D1 receptors (104, 105). In addition, olanzapine acts as an inverse agonist at dopamine D2 receptors (106). The drug is an antagonist at dopamine D3 (107) and D4 receptors (74). At serotonin 5-HT2A and 5-HT2B receptors, olanzapine is a potent antagonist (105). It also exhibits potent antagonist effects at histamine H1 receptors and alpha-1 adrenoceptors (105). Olanzapine is a low affinity antagonist at M1 and M5 muscarinic acetylcholine receptors (105).	Chemical Class: thienobenzodiazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: olanzapine and fluoxetine hydrochloride Trade Name: Symbyax ® [Eli Lilly] Dosage Forms/Routes: Capsule/oral Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem]	Initial Approval: 12/24/2003 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Molecular Mass: 658.23 g/mol	Indications: Depressive episodes associated with bipolar disorder	Possible Mechanisms of Action: Please refer to the entries for olanzapine and fluoxetine hydrochloride.	2D Structure:
Generic Name: oxazepam IUPAC Name: 9-chloro-4-hydroxy-6-phenyl- 2,5-diazabicyclo[5.4.0]undeca- 5,8,10,12-tetraen-3-one Dosage Forms/Routes: Capsule/oral Major Metabolite: oxazepam glucuronide Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 06/04/1965 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₅H₁₁ClN₂O₂ Molecular Mass: 286.713 g/mol	Indications: Anxiety disorders or short-term relief of the symptoms of anxiety; anxiety associated with depression; management of anxiety, tension, agitation, and irritability in older patients; acute tremulousness, inebriation, or anxiety associated with alcohol withdrawal	Possible Mechanism of Action: Oxazepam is a nonselective benzodiazepine agonist (108).	Chemical Class: 3-hydroxy benzodiazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: paliperidone Trade Name: Invega ® [Janssen] IUPAC Name: 3-[2-[4-(6-fluoro-1,2-benzoxazol-3- yl)piperidin-1-yl]ethyl]-9-hydroxy-2- methyl-6,7,8,9-tetrahydropyrido[2,1- b]pyrimidin-4-one Dosage Forms/Routes: Extended release tablet/oral Major Metabolites: Paliperidone is not metabolized extensively, and none of its metabolites could be considered "major." Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/19/2006 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₃H₂₇FN₄O₃ Molecular Mass: 426.483883 g/mol	Indications: Acute and maintenance treatment of schizophrenia	Possible Mechanisms of Action: Paliperidone is a centrally active dopamine Type 2 (D2) antagonist and with predominant serotonin Type 2 (5HT2A) activity (see prescribing information). Paliperidone is also active as an antagonist at α1 and α2 adrenergic receptors and H1 histaminergic receptors (see prescribing information).	Chemical Class: benzisoxazole derivative (major active metabolite of risperidone) PubChem 2D Structure:
Generic Name: paroxetine hydrochloride Trade Name: Paxil ® [GlaxoSmithKline] Common Chemical Name: (-)-trans-4R-(4'- fluorophenyl)-3S-[(3',4'- methylenedioxyphenoxy) methyl] piperidine hydrochloride hemihydrate Dosage Forms/Routes: Tablet/oral; Extended release tablet/oral; Suspension/oral Major Metabolites: (3S,4R)-4-(4-fluorophenyl)-3- hydroxymethyl-1- methylpiperidine; 3S,4R)-4-(4-fluorophenyl)-3- (hydroxymethyl)piperidine; (3S,4R)-4-(4-fluorophenyl)-3- (4- hydroxy-3- methoxyphenoxymethyl) piperidine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/29/1992 Manufacturers: [FDA Search] Product Insert: [Tablet & Suspension] [Extended Release Tablet - Paxil CR] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₉H₂₀FNO₃ ·HCl·1/2H₂O Molecular Mass: 374.8 g/mol	Indications: Major depressive disorder; OCD; panic disorder; social anxiety disorder/social phobia; generalized anxiety disorder (GAD); PTSD	Possible Mechanisms of Action: Paroxetine is a potent serotonin reuptake inhibitor (45). It also has a moderate affinity for the norepinephrine transporter (45). Paroxetine is a low affinity antagonist at some subtypes of muscarinic acetylcholine receptors (45). In addition, paroxetine is a nitric oxide synthase inhibitor (143).	Chemical Class: phenylpiperidine derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: paroxetine mesylate Trade Name: Pexeva ® [Synthon] IUPAC Name: methanesulfonic acid; 3- (benzo[1,3]dioxol-5- yloxymethyl)-4-phenyl-piperidine Dosage Forms/Routes: Tablet/oral Major Metabolites: (3S,4R)-4-(4-fluorophenyl)-3- hydroxymethyl-1- methylpiperidine; 3S,4R)-4-(4-fluorophenyl)-3- (hydroxymethyl)piperidine; (3S,4R)-4-(4-fluorophenyl)-3- (4- hydroxy-3- methoxyphenoxymethyl) piperidine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 07/03/2003 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₀H₂₅NO₆S Molecular Mass: 407.482 g/mol	Indications: Major depressive disorder; OCD; panic disorder; social anxiety disorder/social phobia; generalized anxiety disorder (GAD); PTSD	Possible Mechanisms of Action: Paroxetine is a potent serotonin reuptake inhibitor (45). It also has a moderate affinity for the norepinephrine transporter (45). Paroxetine is a low affinity antagonist at some subtypes of muscarinic acetylcholine receptors (45). In addition, paroxetine is a nitric oxide synthase inhibitor (143).	Chemical Class: phenylpiperidine derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: perphenazine IUPAC Name: 2-[4-[3-(2-chlorophenothiazin- 10-yl)propyl]piperazin-1- yl]ethanol Dosage Forms/Routes: Tablet/oral; Concentrate/oral Major Metabolites: deshydroxyethylperphenazine; perphenazine sulfoxide; 7-hydroxyperphenazine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 02/27/1957 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₁H₂₆ClN₃OS Molecular Mass: 403.969 g/mol	Indications: Schizophrenia; control of severe nausea and vomiting in adults	Possible Mechanisms of Action: Perphenazine is a potent dopamine D2 receptor antagonist (110). It is also an antagonist at dopamine D1 (110), D3 (10), and D4 (10) receptors. At histamine H1 receptors, perphenazine is an antagonist (27). The drug also binds to serotonin 5-HT2A, 5-HT6, and 5-HT7 receptors (27). In addition, perphenazine binds to alpha-1-adrenoceptors (27) and sigma receptors (111).	Chemical Class: piperazinyl phenothiazine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: phenelzine sulfate Trade Name: Nardil ® [Pfizer] IUPAC Name: 2-hydrazinylethylbenzene; sulfuric acid Dosage Forms/Routes: Tablet/oral Major Metabolites: phenylacetic acid; parahydroxyphenylacetic acid Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 06/09/1961 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₈H₁₄N₂O₄S Molecular Mass: 234.274 g/mol	Indications: Depressed patients clinically characterized as "atypical," "nonendogenous," or "neurotic." These patients often have mixed anxiety and depression and phobic or hypochondriacal features. There is less conclusive evidence of its usefulness with severely depressed patients with endogenous features. Nardil should rarely be the first antidepressant drug used. Rather, it is more suitable for use with patients who have failed to respond to the drugs more commonly used for these conditions.	Possible Mechanisms of Action: Phenelzine is an irreversible inhibitor of monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B) (111). The drug also inhibits GABA transaminase and alanine transaminase (111).	Chemical Class: hydrazine derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: prochlorperazine dimaleate Trade Name: Compazine ® [GlaxoSmithKline] IUPAC Name: 2-chloro-10-[3-(4-methyl- 2,3,5,6-tetrahydropyrazin-1- yl)propyl]-10H-phenothiazine; 4-hydroxy-4-oxo-but-2-enoate Dosage Forms/Routes: Tablet/oral; Suppository/rectal Major Metabolite: prochlorperazine sulphoxide Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 10/23/1956 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₄H₂₈ClN₃O₄S Molecular Mass: 606.088 g/mol	Indications: Schizophrenia; control of severe nausea and vomiting; short-term treatment of generalized non-psychotic anxiety (should not be the first drug used in therapy)	Possible Mechanisms of Action: Prochlorperazine is an antagonist at dopamine D2 receptors (112). Prochlorperazine also binds to dopamine D3 (113) and D4 (10) receptors. In addition, the drug binds to serotonin 5-HT2A receptors (29), histamine H1 receptors (114), and alpha-1-adrenoceptors (114).	Chemical Class: piperazine phenothiazine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: protriptyline hydrochloride Trade Name: Vivactil ® [Odyssey] Common Chemical Name: N-methyl-5H-dibenzo[a,d]- cycloheptene-5-propanamine hydrochloride Dosage Forms/Routes: Tablet/oral Major Metabolites: protriptyline 10,11 expoxide; 10-hydroxyprotriptyline; 10,11-dihydroxyprotriptyline Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 09/27/1967 Manufacturers: [FDA Search] Product Insert: [Link] Epocrates: [Link] Empirical Formula: C₁₉H₂₂ClN Molecular Mass: 299.837 g/mol	Indications: Treatment of symptoms of depression in patients who are under close medical supervision. Its activating properties make it particularly suitable for withdrawn and anergic patients	Possible Mechanisms of Action: Protriptyline is a norepinephrine reuptake inhibitor (115). The drug is an antagonist at some subtypes of muscarinic acetylcholine receptors (117, 130). It is also a low affinity antagonist at histamine H1 receptors (102, 130).	Chemical Class: dibenzocycloheptene derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: quazepam Trade Name: Doral ® [MedPointe] IUPAC Name: 9-chloro-6-(2-fluorophenyl)-2- (2,2,2-trifluoroethyl)-2,5- diazabicyclo[5.4.0]undeca- 5,8,10,12-tetraene-3-thione Dosage Forms/Routes: Tablet/oral Major Metabolites: 2-oxoquazepam; N-desalkyl-2-oxoquazepam Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/27/1985 Manufacturers: [FDA Search] Product Insert: [Link] Empirical Formula: C₁₇H₁₁ClF₄N₂S Molecular Mass: 386.795 g/mol	Indications: Short-term treatment of insomnia	Possible Mechanism of Action: Quazepam binds to GABA-A receptor complexes that contain the alpha1 subunit (118).	Chemical Class: trifluoroethyl benzodiazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: quetiapine fumarate Trade Name: Seroquel ® [AstraZeneca] Common Chemical Name: 2-[2-(4-dibenzo [b,f ] [1,4]thiazepin-11-yl-1- piperazinyl)ethoxy]-ethanol fumarate (2:1) (salt) Dosage Forms/Routes: Tablet/oral; Extended release tablet/oral Major Metabolites: quetiapine sulfoxide; 7-hydroxyquetiapine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 09/26/1997 Manufacturers: [FDA Search] Product Insert: [Tablet] [Extended Release Tablet - Seroquel Xr] RxList: [Link] Epocrates: [Link] Empirical Formula: C₄₆H₅₄N₆O₈S₂ Molecular Mass: 883.089 g/mol	Indications: Schizophrenia; acute manic episodes associated with bipolar I disorder, as either monotherapy or adjunct therapy to lithium or divalproex	Possible Mechanisms of Action: Quetiapine is an antagonist at serotonin 5-HT2A receptors (119). It is also a low potency dopamine D2 receptor inverse agonist (106). Quetiapine is an antagonist at alpha-1A-adrenoceptors (25), alpha-1B-adrenoceptors (25), and alpha-2C-adrenoceptors (40). In addition, the drug is a histamine H1 receptor antagonist (27).	Chemical Class: dibenzothiazepine derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: ramelteon Trade Name: Rozerem ® [Takeda] Common Chemical Name: (S)-N-[2-(1,6,7,8-tetrahydro- 2H-indeno-[5,4-b]furan-8- yl)ethyl]propionamide Dosage Forms/Routes: Tablet/oral Major Metabolite: M-II Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/29/1993 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Empirical Formula: C₁₆H₂₁NO₂ Molecular Mass: 259.343 g/mol	Indications: Insomnia characterized by difficulty with sleep onset	Possible Mechanisms of Action: Ramelteon is an agonist at melatonin M1 and M2 receptors.	PubChem 2D Structure:
Generic Name: risperidone Trade Name: Risperdal ® [Janssen] IUPAC Name: 4-[2-[4-(6-fluorobenzo[d] isoxazol-3-yl)-1- piperidyl]ethyl]-3-methyl-2,6- diazabicyclo[4.4.0]deca-1,3- dien-5-one Dosage Forms/Routes: Tablet/oral; Tablet/orally disintegrating; Solution/oral Major Metabolite: 9-hydroxyrisperidone Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/29/1993 Manufacturers: [FDA Search] Product Insert: [Tablets & Solution] [Intramuscular - Risperdal Consta] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₃H₂₇FN₄O₂ Molecular Mass: 410.485 g/mol	Indications: Schizophrenia; short-term treatment of acute manic or mixed episodes associated with bipolar I disorder; combination therapy with lithium or valproate for the short-term treatment of acute manic or mixed episodes associated with bipolar I disorder	Possible Mechanisms of Action: Risperidone is a high potency antagonist at serotonin 5-HT2A receptors (120). The drug also acts as an inverse agonist at dopamine D2 receptors (106) and is an antagonist at D3 and D4 receptors (120). Risperidone is an inverse agonist at serotonin 5-HT1B (121), 5-HT1D (121), and 5-HT2C (38, 122) receptors. It acts as an antagonist at serotonin 5-HT7 (123) receptors. In addition, risperidone is an antagonist at alpha-1A-adrenoceptors (25), alpha-1B-adrenoceptors (25), alpha-2C-adrenoceptors (40), and histamine H1 receptors (27).	Chemical Class: benzisoxazole derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: selegiline transdermal system Trade Name: EMSAM ® [Somerset] IUPAC Name: N-methyl-1-phenyl-N-prop-2- ynyl-propan-2-amine Dosage Forms/Routes: Extended release film/transdermal Major Metabolites: N-desmethylselegiline; L-methamphetamine; L-amphetamine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 02/27/2006 Manufacturers: [FDA Search] Prescribing Information: [Link] RxList: [Link] Empirical Formula: C₁₃H₁₇N Molecular Mass: 187.28078 g/mol	Indications: Major depressive disorder	Possible Mechanisms of Action: Selegiline is an irreversible inhibitor of monoamine oxidase B (MAO-B) and monoamine oxidase A (MAO-A) according to the prescribing information for the drug. Selegiline has a greater affinity for MAO-B and is therefore selective for MAO-B at lower dosages (see the prescribing information).	Chemical Class: levorotatory acetylenic derivative of phenethylamine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: sertraline hydrochloride Trade Name: Zoloft ® [Pfizer] IUPAC Name: 4-(3,4-dichlorophenyl)-N- methyl-tetralin-1-amine hydrochloride Dosage Forms/Routes: Tablet/oral; Concentrate/oral Major Metabolites: desmethylsertraline Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/30/1991 Manufacturers: [FDA Search] Product Insert: [Tablet & Concentrate] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₇H₁₈Cl₃N Molecular Mass: 342.69 g/mol	Indications: Major depressive disorder; OCD in adults, children, and adolescents;, panic disorder; PTSD; premenstrual dysphoric disorder (PMDD); social anxiety disorder	Possible Mechanisms of Action: Sertraline inhibits the reuptake of serotonin (45). It is also a low potency dopamine reuptake inhibitor (16).	PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: temazepam Trade Name: Restoril ® [Tyco Healthcare] IUPAC Name: 9-chloro-4-hydroxy-2-methyl- 6-phenyl-2,5- diazabicyclo[5.4.0]undeca- 5,8,10,12-tetraen-3-one Dosage Forms/Routes: Capsule/oral Major Metabolite: temazepam glucuronide Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 02/27/1981 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₆H₁₃ClN₂O₂ Molecular Mass: 300.739 g/mol	Indications: Short-term treatment of insomnia	Possible Mechanisms of Action: Temazepam is a nonselective benzodiazepine agonist (61).	Chemical Class: 3-hydroxy benzodiazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: thioridazine hydrochloride IUPAC Name: 10-[2-(1-methyl-2- piperidyl)ethyl]-2- methylsulfanyl-phenothiazine hydrochloride Dosage Forms/Routes: Tablet/oral; Concentrate/oral Major Metabolites: mesoridazine; sulforidazine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 03/15/1962 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₁H₂₇ClN₂S₂ Molecular Mass: 407.037 g/mol	Indications: Management of schizophrenic patients who fail to respond adequately with other antipsychotic drugs	Possible Mechanisms of Action: Thioridazine binds to dopamine D2, D3, and D4 receptors (67). The drug is an antagonist at serotonin 5-HT2A receptors (24). Thioridazine is also an antagonist at alpha-1A-adrenoceptors and alpha-1B-adrenoceptors (25). In addition, it is an antagonist at M1, M2, M3, M4, and M5 muscarinic acetylcholine receptors (28). Finally, thioridazine is an antagonist at histamine H1 receptors (27).	Chemical Class: piperidine phenothiazine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: thiothixene Trade Name: Navane ® [Pfizer] IUPAC Name: N,N-dimethyl-9-[3-(4- methylpiperazin-1- yl)propylidene]thioxanthene-2- sulfonamide Dosage Forms/Routes: Capsule/oral; Injectable/injection; Concentrate/oral Major Metabolites: N/A (E-mail Shawn if you can provide this information.) Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 07/24/1967 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₃H₂₉N₃O₂S₂ Molecular Mass: 443.627 g/mol	Indications: Schizophrenia	Possible Mechanisms of Action: Thiothixene binds to dopamine D2 receptors, histamine H1 receptors, alpha-1A-adrenoceptors, and serotonin 5-HT7 receptors (27). It also has a moderate affinity for alpha-1B-adrenoceptors (67).	Chemical Class: thioxanthene PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: tranylcypromine sulfate Trade Name: Parnate ® [GlaxoSmithKline] IUPAC Name: (2-phenylcyclopropyl) ammonium sulfate Dosage Forms/Routes: Tablet/oral Major Metabolites: N-acetyltranylcypromine; p-hydroxytranylcypromine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 02/21/1961 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₈H₂₄N₂O₄S Molecular Mass: 364.46 g/mol	Indications: Major depressive episode without melancholia	Possible Mechanisms of Action: Tranylcypromine is an irreversible inhibitor of monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B) (125).	Chemical Class: cyclopropylamine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: trazodone hydrochloride IUPAC Name: 8-[3-[4-(3- chlorophenyl)piperazin-1- yl]propyl]-6,8,9- triazabicyclo[4.3.0]nona-2,4,9- trien-7-one hydrochloride Dosage Forms/Routes: Tablet/oral Major Metabolite: m-chlorophenylpiperazine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/24/1981 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₉H₂₃Cl₂N₅O Molecular Mass: 408.324 g/mol	Indications: Major depressive disorder	Possible Mechanisms of Action: Trazodone and its active metabolite, m-chlorophenylpiperazine (m-CPP), are partial agonists at serotonin 5-HT1A receptors (126). At serotonin 5-HT2A and 5-HT2B receptors, trazodone is an antagonist (127). Trazodone and m-CPP are full agonists at serotonin 5-HT2C receptors (128). However, trazodone has a much lower affinity for 5-HT2C receptors than m-CPP (127). The drug is an antagonist at alpha-1-adrenoceptors (129, 130) and a very low affinity antagonist at histamine H1 receptors (130). In addition, m-CPP causes the extracellular release of serotonin through the serotonin transporter (131).	Chemical Class: triazolopyridine derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: triazolam Trade Name: Halcion ® [Pfizer] Common Chemical Name: 8-chloro-6-(o-chlorophenyl)-1- methyl -4H-s-triazolo-(4,3- alpha)(1,4) benzodiazepine Dosage Forms/Routes: Tablet/oral Major Metabolites: alpha-hydroxytriazolam; 4-hydroxytriazolam Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 11/15/1982 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₇H₁₂Cl₂N₄ Molecular Mass: 343.21 g/mol	Indications: Short-term treatment of insomnia	Possible Mechanism of Action: Triazolam is a nonselective benzodiazepine agonist (132).	Chemical Class: triazolo benzodiazepine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: trifluoperazine dihydrochloride Trade Name: Stelazine ® [GlaxoSmithKline] IUPAC Name: 10-[3-(4-methylpiperazin-1- yl)propyl]-2- (trifluoromethyl)phenothiazine dihydrochloride Dosage Forms/Routes: Tablet/oral; Concentrate/oral Major Metabolites: N-desmethyltrifluoperazine; 7-hydroxytrifluoperazine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 04/16/1959 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₁H₂₆Cl₂F₃N₃S Molecular Mass: 480.418 g/mol	Indications: Schizophrenia; short-term treatment of generalized non-psychotic anxiety (should not be used as the first drug in therapy for most patients)	Possible Mechanisms of Action: Trifluoperazine is an inverse agonist at dopamine D2 receptors (133). The drug also binds with moderate affinity to dopamine D4 receptors (134). The drug is an antagonist at serotonin 5-HT2A receptors (135) as well as alpha-1A-adrenoceptors and alpha-1B-adrenoceptors (25). Trifluoperazine is a low affinity antagonist at histamine H1 receptors (136). In addition, the drug inhibits interactions between calmodulin and proteins (137).	Chemical Class: piperazine phenothiazine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: trimipramine maleate Trade Name: Surmontil ® [Odyssey] Common Chemical Name: 5-(3-dimethylamino-2- methylpropyl)-10,11-dihydro- 5H-dibenz (b,f) azepine acid maleate (racemic form) Dosage Forms/Routes: Capsule/oral Major Metabolites: desmethyltrimipramine 2-hydroxytrimipramine; 2-hydroxydesmethyltrimipramine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 06/12/1979 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₄H₃₀N₂O₄ Molecular Mass: 410.506 g/mol	Indications: Major depressive disorder, especially endogenous depression	Possible Mechanisms of Action: Trimipramine is an antagonist at alpha-1A-adrenoceptors and alpha-1B-adrenoceptors (130, 138) as well as histamine H1 receptors (130). The drug also displays high affinities for serotonin 5-HT2A receptors and dopamine D2 receptors (138).	Chemical Class: dibenzazepine (tertiary tricyclic) PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: venlafaxine hydrochloride Trade Name: Effexor ® [Wyeth] IUPAC Name: 1-[2-dimethylamino-1-(4- methoxyphenyl)- ethyl]cyclohexan-1-ol hydrochloride Dosage Forms/Routes: Tablet/oral; Extended release capsule/oral Major Metabolite: O-desmethylvenlafaxine Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/28/1993 Manufacturers: [FDA Search] Product Insert: [Tablet] [Extended Release Capsule - Effexor XR] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₇H₂₈ClNO₂ Molecular Mass: 313.862 g/mol	Indications: Major depressive disorder, generalized anxiety disorder (XR version only), panic disorder (XR version only), social anxiety disorder (XR version only)	Possible Mechanisms of Action: Venlafaxine inhibits the reuptake of serotonin and norepinephrine (139, 140). It has a much greater affinity for the serotonin transporter (139).	Chemical Class: phenethylamine bicyclic derivative PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: zaleplon Trade Name: Sonata ® [King/Wyeth] IUPAC Name: N-[3-(9-cyano-2,6,7- triazabicyclo[4.3.0]nona- 2,4,7,9-tetraen-5-yl)phenyl]- N-ethyl-ethanamide Dosage Forms/Routes: Capsule/oral Major Metabolite: 5-oxo-zaleplon Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 08/13/1999 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₁₇H₁₅N₅O Molecular Mass: 305.334 g/mol	Indications: Short-term treatment of insomnia	Possible Mechanism of Action: Zaleplon binds to GABA-A receptor complexes that contain the alpha1 subunit(132).	Chemical Class: pyrazolopyrimidine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: ziprasidone hydrochloride monohydrate Trade Name: Geodon ® [Pfizer] IUPAC Name: 6-chloro-5-[2-[4-(7-thia-8- azabicyclo[4.3.0]nona-1,3,5,8- tetraen-9-yl)piperazin-1- yl]ethyl]-1,3-dihydroindol-2- one hydrate hydrochloride Dosage Forms/Routes: Capsule/oral Major Metabolites: benzisothiazole sulphoxide; benzisothiazole sulphone; ziprasidone sulphoxide; S-methyl-dihydroziprasidone Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Manufacturer: Pfizer Initial Approval: 02/05/2001 Manufacturers: [FDA Search] Product Insert: [Link] RxList: [Link] Epocrates: [Link] Empirical Formula: C₂₁H₂₄Cl₂N₄O₂S Molecular Mass: 467.412 g/mol	Indications: Schizophrenia; acute manic or mixed episodes associated with bipolar disorder, with or without psychotic features	Possible Mechanisms of Action: Ziprasidone is an antagonist at serotonin 5-HT2A receptors and dopamine D2 receptors (141). The drug is a partial agonist at serotonin 5-HT1B receptors and an inverse agonist at 5-HT1D receptors (121). Ziprasidone is also an inverse agonist at 5-HT2C receptors (38). The drug is an agonist at 5-HT1A receptors (142) and is known to bind to 5-HT7 receptors (27). Ziprasidone may bind to dopamine D1, D3, and D4 receptors (67). Finally, ziprasidone is a low affinity antagonist at alpha-1-adrenoceptors and histamine H1 receptors (141).	Chemical Class: benzisothiazolyl piperazine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]
Generic Name: zolpidem tartrate Trade Name: Ambien ® [Sanofi-Aventis] IUPAC Name: 2,3-dihydroxybutanedioic acid; N,N-dimethyl-2-[4-methyl-8- (4-methylphenyl)-6,9- diazabicyclo[4.3.0]nona- 2,4,7,9-tetraen-7-yl]- ethanamide Dosage Forms/Routes: Tablet/oral; Extended release tablet/oral Major Metabolite: "M-3" Database Search Links: [PubMed] [Search PubMed for Randomized Controlled Trials] [PubChem] [PDSP K_i database]	Initial Approval: 12/16/1992 Manufacturers: [FDA Search] Product Insert: [Tablet] [Extended Release Tablet - Ambien CR] RxList: [Link] [Link] (CR) Epocrates: [Link] Empirical Formula: C₄₂H₄₈N₆O₈ Molecular Mass: 764.866 g/mol	Indications: Short-term treatment of insomnia	Possible Mechanism of Action: Zolpidem binds to GABA-A receptor complexes that contain the alpha1 subunit (132).	Chemical Class: imidazopyridine PubChem 2D Structure: "3D" Structure (Requires Chime): [Link]

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