Generic Name:
alfentanil hydrochloride

Trade Name:
Alfenta ® [Akorn]

IUPAC Name:
N-[1-[2-(4-ethyl-5-oxo-tetrazol-1-
yl)ethyl]-4-(methoxymethyl)-4-
piperidyl]-N-phenyl-propanamide
hydrochloride

Dosage Forms/Routes:
injectable/injection

Major Metabolites:
noralfentanil;
N-phenylpropionamide

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
12/29/1986

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link]

RxList:
[Link]

Empirical Formula:
C₂₁H₃₃ClN₆O₃

Molecular Mass:
452.978 g/mol

Possible Mechanism of Action:
Alfentanil is a mu opioid receptor agonist (1).

Indications:
Alfentanil is indicated:
--as an analgesic adjunct given in incremental doses in the maintenance of anesthesia with barbiturate/ nitrous oxide/ oxygen;

--as an analgesic administered by continuous infusion with nitrous oxide/ oxygen in the maintenance of general anesthesia;

--as a primary anesthetic agent for the induction of anesthesia in patients undergoing general surgery in which endotracheal intubation and mechanical ventilation are required;

--as the analgesic component for monitored anesthesia care (MAC).

Chemical Class:
piperanilide

PubChem 2D Structure:

Generic Name:
buprenorphine hydrochloride

Trade Name:
Subutex ® [Reckitt Benckiser]

IUPAC Name:
(2S)-2-[(-)-(5R,6R,7R,14S)-
9α-cyclopropylmethyl-4,5-epoxy-
6,14-ethanomorphinan-7-yl]-3-hydroxy-
6-methoxy-3,3-dimethylbutan-2-ol

Dosage Forms/Routes:
tablet/sublingual;
injectable/injection

Major Metabolites:
norbuprenorphine

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
10/08/2002

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link]

RxList:
[Link]

Empirical Formula:
C₂₉H₄₂ClNO₄

Molecular Mass:
504.101 g/mol

Possible Mechanisms of Action:
Buprenorphine is a partial agonist at mu opioid receptors and nociceptin/orphanin FQ (ORL1) receptors (2). The drug has a higher affinity for the former receptors (2). Buprenorphine exhibits antagonist activity at kappa opioid receptors and delta opioid receptors, with less potent effects at the latter (3). The drug may also act as an antagonist at epsilon opioid receptors (4). Buprenorphine's active metabolite norbuprenorphine is a partial agonist at mu and kappa receptors and a full agonist at delta and ORL1 receptors (2).

Indications:
Buprenorphine is indicated for the treatment of opioid dependence.

Chemical Class:
oripavine derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
butorphanol tartrate

Trade Name:
Stadol ® [Apothecon]

IUPAC Name:
17-cyclobutylmethyl-
morphinan-3,14-diol

Dosage Forms/Routes:
injectable/injection
spray, metered/nasal

Major Metabolites:
norbutorphanol;
hydroxybutorphanol

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
08/22/1978

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link]

RxList:
[Link]

Empirical Formula:
C₂₅H₃₅NO₈

Molecular Mass:
477.547 g/mol

Possible Mechanisms of Action:
Butorphanol's primary effect involves partial agonism at mu opioid receptors (5). In addition, butorphanol is a full agonist at delta opioid receptors (6). At kappa opioid receptors, the drug is likely to act as a full agonist (7).

Indications:
Injectable butorphanol tartrate and butorphanol tartrate nasal spray are indicated for the management of pain when the use of an opioid analgesic is appropriate.

Injectable butorphanol is also indicated as a preoperative or preanesthetic medication, as a supplement to balanced anesthesia, and for the relief of pain during labor.

Chemical Class:
morphinan derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
codeine phosphate

IUPAC Name:
7,8-didehydro-4,5-epoxy-3-methoxy-
17-methylmorphinan-6-ol

Dosage Forms/Routes:
[This drug is often combined with other medications.]
tablet/oral;
capsule/oral;
syrup/oral;
solution/oral

Major Metabolites:
codeine-6-glucuronide;
morphine;
normorphine;
norcodeine;
morphine-3-glucuronide;
morphine-6-glucuronide

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link] (Tylenol® with codeine)

RxList:
[Link]

Empirical Formula:
C₃₆H₅₀N₂O₁₅P₂

Molecular Mass:
812.734 g/mol

Possible Mechanisms of Action:
Codeine must be metabolized in order for its analgesic activity to be exhibited (8,9). Codeine analgesia is primarily due to its metabolism to codeine-6-glucuronide (8). To a much lesser degree, the metabolism of codeine to morphine may contribute to codeine- induced analgesia (9). Codeine-6-glucuronide binds with high affinity to mu opioid receptors (10). Codeine-6-glucuronide also binds to delta opioid receptors and is less selective for mu opioid receptors than its parent compound (10).

Indications:
Codeine is indicated for the relief of mild to moderate pain. Some formulations of the drug are also indicated as cough suppressants.

Chemical Class:
phenanthrene (opium alkaloid)

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
dihydrocodeine bitartrate

IUPAC Name:
4,5-alpha-epoxy-3-methoxy-17-
morphinan-6-ol

Dosage Forms/Routes:
tablet/oral;
capsule/oral

Major Metabolites:
dihydromorphine;
dihydromorphine-6-glucuronide;
nordihydrocodeine;
dihydrocodeine-6-glucuronide;
dihydromorphine-3-glucuronide

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
07/07/1958

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link] (Synalgos® DC)

Empirical Formula:
C₂₂H₂₉NO₉

Molecular Mass:
451.467 g/mol

Possible Mechanism of Action:
Dihydrocodeine is an agonist at mu opioid receptors (11).

Indications:
Dihydrocodeine bitartrate is indicated for the relief of moderate to moderately severe pain.

Chemical Class:
semisynthetic phenanthrene derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
fentanyl

Trade Name:
Duragesic ® [Alza/Janssen]

IUPAC Name:
NN-(1-phenethyl-4-piperidyl)-N-
phenyl-propanamide

Dosage Forms/Routes:
film (extended release); transdermal

Major Metabolites:
norfentanyl

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
08/07/1990

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link]

RxList:
[Link]

Empirical Formula:
C₂₂H₂₈N₂O

Molecular Mass:
336.471 g/mol

Possible Mechanism of Action:
Fentanyl is an agonist at mu opioid receptors (12).

Indications:
DURAGESIC® is indicated for management of persistent, moderate to severe chronic pain that:

— requires continuous, around-the-clock opioid administration for an extended period of time, and

— cannot be managed by other means such as non-steroidal analgesics, opioid combination products, or immediate-release opioids

DURAGESIC® should ONLY be used in patients who are already receiving opioid therapy, who have demonstrated opioid tolerance, and who require a total daily dose at least equivalent to DURAGESIC® 25 mcg/h. Patients who are considered opioid-tolerant are those who have been taking, for a week or longer, at least 60 mg of morphine daily, or at least 30 mg of oral oxycodone daily, or at least 8 mg of oral hydromorphone daily or an equianalgesic dose of another opioid.

Chemical Class:
piperanilide

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
fentanyl citrate

Trade Name:
Sublimaze ® [Akorn]

IUPAC Name:
2-hydroxypropane-1,2,3-tricarboxylic
acid; N-(1-phenethyl-4-piperidyl)-N-
phenyl-propanamide

Dosage Forms/Routes:
injectable/injection;
film (extended release)/transdermal
tablet/buccal;
lozenge/transmucosal

Major Metabolites:
norfentanyl

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
02/19/1968

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link] (Sublimaze® Injectable)

[Link] (Actiq®)

[Link] (Fentora®)

RxList:
[Link]

Empirical Formula:
C₂₈H₃₆N₂O₈

Molecular Mass:
528.594 g/mol

Possible Mechanism of Action:
Fentanyl is an agonist at mu opioid receptors (12).

Indications:
SUBLIMAZE (fentanyl citrate) is indicated:
— for analgesic action of short duration during the anesthetic periods, premedication, induction and maintenance, and in the immediate
postoperative period (recovery room) as the need arises.
— for use as a narcotic analgesic supplement in general or regional anesthesia.
— for administration with a neuroleptic as an anesthetic premedication, for the induction of anesthesia and as an adjunct in the
maintenance of general and regional anesthesia.
— for use as an anesthetic agent with oxygen in selected high risk patients, such as those undergoing open heart surgery or certain
complicated neurological or orthopedic procedures.

ACTIQ® is indicated only for the management of breakthrough
cancer pain in patients with malignancies who are already
receiving and who are tolerant to opioid therapy for their
underlying persistent cancer pain. Patients considered opioid
tolerant are those who are taking at least 60 mg morphine/day, at
least 25 mcg transdermal fentanyl/hour, at least 30 mg of
oxycodone daily, at least 8 mg oral hydromorphone daily or an
equianalgesic dose of another opioid for a week or longer.

Chemical Class:
piperanilide

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
fentanyl hydrochloride

Trade Name:
Ionsys ® [Alza/Ortho-McNeil]

IUPAC Name:
N-(1-phenethyl-4-piperidyl)-N-
phenyl-propanamide hydrochloride

Dosage Form:
iontophoretic transdermal system

Major Metabolites:
norfentanyl

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
05/22/2006

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link]

RxList:
[Link]

Empirical Formula:
C₂₂H₂₉ClN₂O

Molecular Mass:
372.931 g/mol

Possible Mechanism of Action:
Fentanyl is an agonist at mu opioid receptors (12).

Indications:
IONSYS™ is indicated for the short-term management of acute postoperative pain in adult patients requiring opioid analgesia during hospitalization. Patients should be titrated to an acceptable level of analgesia before initiating treatment with IONSYS™. IONSYS™ is not intended for home use
and is, therefore, inappropriate for use in patients once they have been discharged from the
hospital. It is not recommended for patients under the age of 18 years

Chemical Class:
piperanilide

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
hydrocodone bitartrate

Trade Name:
Vicodin ® [Abbott] (hydrocodone bitartrate combined with acetaminophen)

Common Chemical Name:
4,5α-epoxy-3-methoxy-
17-methylmorphinan-6-one tartrate (1:1) hydrate (2:5)

Dosage Forms/Routes:
tablet/oral;
capsule/oral;
solution/oral;
suspension/oral

Major Metabolites:
hydromorphone;
norhydrocodone

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
01/07/1983

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link] (generic hydrocodone bitartrate plus acetaminophen)

RxList:
[Link]

Empirical Formula:
C₁₈H₂₁NO₃•C₄H₆O₆•
2½ H₂O

Molecular Mass:
494.490 g/mol

Possible Mechanism of Action:
Hydrocodone is a mu opioid receptor agonist. (13).

Indications:
Hydrocodone is indicated for the treatment of moderate to moderately severe pain.

Chemical Class:
phenanthrene derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
hydromorphone hydrochloride

Trade Name:
Dilaudid ® [Abbott]

Common Chemical Name:
4,5α-epoxy-3-hydroxy-
17-methylmorphinan-6-one hydrochloride

Dosage Forms/Routes:
tablet/oral;
solution/oral;
injectable/injection;
extended release capsule; oral

Major Metabolites:
hydromorphone-3-glucuronide;
hydromorphone-3-glucoside;
dihydroisomorphine-6-glucuronide

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
01/11/1984

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link]

RxList:
[Link]

Empirical Formula:
C₁₇H₂₀ClNO₃

Molecular Mass:
321.798 g/mol

Possible Mechanism of Action:
Hydromorphone is a mu opioid receptor agonist (14).

Indications:
Hydromorphone is indicated for the management of pain in patients where an opioid analgesic is appropriate.

Chemical Class:
morphinan derivative

PubChem 2D Structure:

Generic Name:
levorphanol tartrate

Trade Name:
Levo-Dromoran ® [Valeant]

Common Chemical Name:
levo-3-hydroxy-N-methylmorphinan

Dosage Forms/Routes:
tablet/oral

Major Metabolites:
levorphanol glucuronide

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
01/08/1953

Manufacturers:
[FDA Search]

RxList:
[Link]

Empirical Formula:
C₂₁H₃₃NO₉

Molecular Mass:
443.488 g/mol

Possible Mechanisms of Action:
Levorphanol binds with high affinity to mu, kappa, and delta opioid receptors (15). The drug has been identified as a full agonist at kappa opioid receptors (16). Furthermore, it binds with high affinity to kappa1 and kappa3 but not kappa2 receptors (17). Levorphanol may also exhibit non-competitive NMDA antagonist activity at high doses (18).

Indications:
Levorphanol is indicated for the management of moderate to severe pain or as a preoperative medication where an opioid analgesic is appropriate.

Chemical Class:
morphinan derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link]

Generic Name:
meperidine

Trade Name:
Demerol ® [Sanofi-Aventis]

IUPAC Name:
ethyl 1-methyl-4-phenyl-piperidine-
4-carboxylate hydrochloride

Dosage Forms/Routes:
tablet/oral

Major Metabolites:
normeperidine

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
11/10/1942

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link]

RxList:
[Link]

Empirical Formula:
C₁₅H₂₂ClNO₂

Molecular Mass:
283.793 g/mol

Possible Mechanisms of Action:
Meperidine is a partial agonist at mu opioid receptors (22, 5). The drug also inhibits the serotonin reuptake transporter (23).

Indications:
Meperidine is indicated:
— For the relief of moderate to severe pain (parenteral and oral forms)
— For preoperative medication (parenteral form only)
— For support of anesthesia (parenteral form only)
— For obstetrical analgesia (parenteral form only)

Chemical Class:
phenylpiperidine

PubChem 2D Structure:

Generic Name:
methadone hydrochloride

Trade Name:
Dolophine ® [Roxane]

IUPAC Name:
6-dimethylamino-4,4-diphenyl-
heptan-3-one hydrochloride

Dosage Forms/Routes:
tablet/oral;
injectable/injection;
concentrate/oral;
solution/oral

Major Metabolites:
2-ethylidene-1,5-dimethyl-3,3-
diphenylpyrrolidine (EDDP);
2-ethyl-5-methyl-3,3-diphenyl-1-
pyrroline (EMDP)

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
08/13/1947

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link]

RxList:
[Link]

Empirical Formula:
C₂₁H₂₈ClNO

Molecular Mass:
345.906 g/mol

Possible Mechanisms of Action:
Methadone is a mu opioid receptor agonist (19, 20). Based on its intermediate efficacy at activating mu opioid receptors, methadone desensitizes the receptors disproportionally more than comparable opioids (20). In addition, methadone may bind to kappa3 opioid receptors (21).

Indications:
Methadone is indicated:
— For the treatment of moderate to severe pain not responsive to non-narcotic analgesics.
— For detoxification treatment of opioid addiction (heroin or other morphine-like drugs).
— For maintenance treatment of opioid addiction (heroin or other morphine-like drugs), in conjunction with
appropriate social and medical services.

Chemical Class:
phenylheptylamine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link]

Generic Name:
morphine sulfate

Trade Name:
MS Contin ® [Purdue Pharma]

Common Chemical Name:
7,8-didehydro-4,5α-epoxy-17-
methylmorphinan-
3,6α-diol sulfate (2:1) (salt)
pentahydrate

Dosage Forms/Routes:
tablet/oral;
extended release tablet/oral;
extended release capsule/oral;
injectable/injection;
injectable, liposomal; injection

Major Metabolites:
morphine-6-glucuronide (M6G);
morphine-3-glucuronide (M3G)

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link] (MS Contin®)

RxList:
[Link] (MS Contin®)

[Link] (Roxanol®)

[Link] (Duramorph®)

DrugBank:
[Link]

Empirical Formula:
(C₁₇H₁₉NO₃)₂·H₂SO₄·5H₂O

Molecular Mass:
758.83 g/mol

Possible Mechanisms of Action:
Morphine and its key active metabolite, morphine-6-glucuronide (M6G), activate mu opioid receptors. Morphine and M6G are partial agonists at some splice variants of the mu opioid receptor and full agonists at other splice variants of the receptor (24). To a much lesser degree, morphine and M6G may act as agonists at kappa and delta opioid receptors (25). Morphine has a higher affinity for kappa opioid receptors than M6G, but morphine has less affinity than M6G for delta opioid receptors (25). Morphine is a partial agonist at delta receptors (6).

Indications:
Immediate release morphine tablets are indicated for the relief of severe acute and severe chronic pain.

Sustained release morphine tablets and capsules are indicated for the relief of pain in patients who require opioid analgesics for more than a few days.

Duramorph® is a systemic narcotic analgesic for administration by the intravenous, epidural or intrathecal routes. It is used for the management of pain not responsive to non-narcotic analgesics. Duramorph® administered epidurally or intrathecally, provides pain relief for extended periods without attendant loss of motor, sensory or sympathetic function.

Chemical Class:
phenanthrene (opium alkaloid)

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
nalbuphine hydrochloride

Trade Name:
Nubain ® [Endo]

Common Chemical Name:
17-(cyclobutylmethyl)-4,5a-
epoxymorphinan-3,6a,14-triol
hydrochloride

Dosage Forms/Routes:
injectable/injection

Major Metabolites:
noroxymorphine

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
05/15/1979

Manufacturers:
[FDA Search]

RxList:
[Link]

Empirical Formula:
C₂₁H₂₈ClNO₄

Molecular Mass:
393.904 g/mol

Possible Mechanisms of Action:
Nalbuphine is a partial agonist at mu opioid receptors (22, 5). The drug is also a partial agonist at kappa opioid receptors (7).

Indications:
Nalbuphine is indicated for the relief of moderate to severe pain. Nalbuphine can also be used as a supplement to balanced anesthesia, for preoperative and postoperative analgesia, and for obstetrical analgesia during labor and delivery.

Chemical Class:
morphinan derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
oxycodone hydrochloride

Trade Name:
Oxycontin ® [Purdue Pharma]

IUPAC Name:
4, 5-epoxy-14-hydroxy-3- methoxy-
17-methylmorphinan-6-one
hydrochloride

Dosage Forms/Routes:
tablet/oral;
extended release tablet/oral;
capsule/oral;
solution/oral

Major Metabolites:
oxymorphone;
noroxymorphone;
noroxycodone

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
4/12/1950

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link] (Oxycontin)

[Link] (Percocet)

[Link] (Percodan)

RxList:
[Link]

Empirical Formula:
C₁₈H₂₂ClNO₄

Molecular Mass:
351.824 g/mol

Possible Mechanism of Action:
Oxycodone is a mu opioid receptor agonist (26). Kappa opioid receptor agonism and oxycodone's metabolites probably do not contribute to the drug's mechanism of action (26).

Indications:
In immediate-release formulations, oxycodone hydrochloride is indicated for the treatment of moderate to moderately severe pain.

OxyContin Tablets are a controlled-release oral formulation of oxycodone hydrochloride indicated for the management of moderate to severe pain when a continuous, around-the-clock analgesic is needed for an extended period of time.

OxyContin is NOT intended for use as a prn analgesic.

Physicians should individualize treatment in every case, initiating therapy at the appropriate point along a progression from non-opioid analgesics, such as non-steroidal antiinflammatory drugs and acetaminophen to opioids in a plan of pain management such as outlined by the World Health Organization, the Agency for Healthcare Research and Quality
(formerly known as the Agency for HealthCare Policy and Research), the Federation of State
Medical Boards Model Guidelines, or the American Pain Society.

OxyContin is not indicated for pain in the immediate postoperative period (the first 12-24 hours following surgery), or if the pain is mild, or not expected to persist for an extended period of time. OxyContin is only indicated for postoperative use if the patient is already receiving the drug prior to surgery or if the postoperative pain is expected to be moderate to severe and persist for an extended period of time. Physicians should individualize treatment, moving from parenteral to oral analgesics as appropriate. (See American Pain Society guidelines.)

Chemical Class:
semisynthetic phenanthrene derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
oxymorphone hydrochloride

Trade Name:
Opana ® [Endo]

Common Chemical Name:
4, 5a-epoxy-3, 14-dihydroxy-17-
methylmorphinan-6-one hydrochloride

Dosage Forms/Routes:
tablet/oral;
extended release tablet/oral;
injectable/injection

Major Metabolites:
oxymorphone-3-glucuronide;
6-OH-oxymorphone

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
04/02/1959

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link] (Opana immediate release)

[Link] (Opana ER)

RxList:
[Link]

Empirical Formula:
C₁₇H₂₀ClNO₄

Molecular Mass:
337.798 g/mol

Possible Mechanism of Action:
Oxymorphone is a mu opioid receptor agonist (26)

Indications:
Opana immediate release is indicated for the relief of moderate to severe acute pain where the use of an opioid is appropriate.

Opana ER is indicated for the relief of moderate to severe pain in patients requiring continuous, around-the-clock opioid treatment for an extended period of time.

Opana ER is not intended for use as a prn analgesic.

Opana ER is not indicated for pain in the immediate post-operative period (12-24 hours following surgery) for patients not previously taking opioids because of the risk of oversedation and respiratory depression requiring reversal with opioid antagonists. Opana ER is not indicated for pain in the post-operative period if the pain is mild or not expected to persist for an extended period of time.

Chemical Class:
semisynthetic phenanthrene derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link]

Generic Name:
pentazocine hydrochloride

Trade Name:
Talacen ® [Endo]

Common Chemical Name:
1,2,3,4,5,6-hexahydro-6,11-dimethyl-
3-(3-methyl-2-butenyl)-2,6-methano-
3-benzazocin-8-ol hydrochloride

Dosage Forms/Routes:
tablet/oral

Major Metabolites:
pentazocine glucuronide

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
02/03/1969

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link]

RxList:
[Link]

Empirical Formula:
C₁₉H₂₈ClNO

Molecular Mass:
321.884 g/mol

Possible Mechanisms of Action:
Pentazocine is likely to be a partial agonist at mu opioid receptors (27). The drug is also a partial agonist at kappa opioid receptors (16).

Indications:
Pentazocine hydrochloride is indicated for the treatment of mild to moderate pain.

Chemical Class:
benzomorphan derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
pentazocine lactate

Trade Name:
Talwin ® [Hospira]

Common Chemical Name:
1,2,3,4,5,6-hexahydro-6,11-dimethyl-
3-(3-methyl-2-butenyl)-2,6-methano-
3-benzazocin-8-ol lactate

Dosage Forms/Routes:
injectable/injection

Major Metabolites:
pentazocine glucuronide

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
07/24/1967

Manufacturers:
[FDA Search]

Empirical Formula:
C₂₂H₃₃NO₄

Molecular Mass:
375.502 g/mol

Possible Mechanisms of Action:
Pentazocine is likely to be a partial agonist at mu opioid receptors (27). The drug is also a partial agonist at kappa opioid receptors (16).

Indications:
Pentazocine lactate is indicated for the treatment of moderate to severe pain. The drug is also indicated as a preoperative or preanesthetic medication and as a supplement to surgical anesthesia.

Chemical Class:
benzomorphan derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
propoxyphene hydrochloride

Trade Name:
Darvon ® [Xanodyne]

IUPAC Name:
[(2S,3R)-4-dimethylamino-3-methyl-
1,2-diphenyl-butan-2-yl] propanoate
hydrochloride

Dosage Forms/Routes:
tablet/oral;
capsule/oral

Major Metabolites:
norpropoxyphene

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
08/16/1957

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link]

RxList:
[Link]

Empirical Formula:
C₂₂H₃₀ClNO₂

Molecular Mass:
375.932 g/mol

Possible Mechanism of Action:
Propoxyphene is a weak mu opioid receptor agonist (28). A metabolite of the drug, norpropoxyphene, may induce cardiotoxic effects that result from an alteration of sodium and potassium ion permeability in cardiac tissue (37).

Indications:
Propoxyphene hydrochloride is indicated for the treatment of mild to moderate pain.

Chemical Class:
phenylheptylamine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
propoxyphene napsylate

Trade Name:
Darvon-N ® [x]

IUPAC Name:
[(2S,3R)-4-dimethylamino-3-methyl-
1,2-diphenyl-butan-2-yl] propanoate;
naphthalene-2-sulfonic acid

Dosage Forms/Routes:
tablet/oral

Major Metabolites:
norpropoxyphene

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
09/09/1971

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link]

RxList:
[Link]

Empirical Formula:
C₃₂H₃₇NO₅S

Molecular Mass:
547.706 g/mol

Possible Mechanism of Action:
Propoxyphene is a weak mu opioid receptor agonist (28). A metabolite of the drug, norpropoxyphene, may induce cardiotoxic effects that result from an alteration of sodium and potassium ion permeability in cardiac tissue (37).

Indications:
Propoxyphene napsylate is indicated for the treatment of mild to moderate pain.

Chemical Class:
phenylheptylamine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
remifentanil hydrochloride

Trade Name:
Ultiva ® [Abbott]

IUPAC Name:
methyl 1-(2-methoxycarbonylethyl)-
4-(phenyl-propanoyl-amino)piperidine-
4-carboxylate hydrochloride

Dosage Forms/Routes:
injectable/injection

Major Metabolites:
remifentanil acid

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
07/12/1996

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link]

RxList:
[Link]

Empirical Formula:
C₂₀H₂₉ClN₂O₅

Molecular Mass:
412.907 g/mol

Possible Mechanisms of Action:
Remifentanil is an agonist at mu opioid receptors (29, 30).

Indications:
Remifentanil is indicated for IV administration:
1. As an analgesic agent for use during the induction and maintenance of general anesthesia for inpatient and outpatient procedures.
2. For continuation as an analgesic into the immediate postoperative period in adult patients under the direct supervision of an anesthesia practitioner in a postoperative anesthesia care unit or intensive care setting.
3. As an analgesic component of monitored anesthesia care in adult patients.

Chemical Class:
piperanilide

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link] 

Generic Name:
sufentanil citrate

Trade Name:
Sufenta ® [Akorn]

IUPAC Name:
2-hydroxypropane-1,2,3-tricarboxylic
acid; N-[4-(methoxymethyl)-1-(2-
thiophen-2-ylethyl)-4-piperidyl]-N-
phenyl-propanamide

Dosage Forms/Routes:
injectable/injection

Major Metabolites:
norsufentanil

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
05/04/1984

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link]

Empirical Formula:
C₂₈H₃₈N₂O₉S

Molecular Mass:
578.675 g/mol

Possible Mechanisms of Action:
Sufentanil is a mu opioid receptor agonist (31).

Indications:
Sufenta (sufentanil citrate) is indicated for intravenous administration in adults and pediatric patients:
— as an analgesic adjunct in the maintenance of balanced general anesthesia in patients who are intubated and ventilated.
— as a primary anesthetic agent for the induction and maintenance of anesthesia with 100% oxygen in patients undergoing major surgical procedures, in patients who are intubated and ventilated, such as cardiovascular surgery or neurosurgical procedures in the sitting position, to provide favorable myocardial
and cerebral oxygen balance or when extended postoperative ventilation is anticipated.

Sufentanil citrate is indicated for epidural administration as an analgesic combined with low dose bupivacaine, usually 12.5 mg per administration,
during labor and vaginal delivery.

Chemical Class:
piperanilide

PubChem 2D Structure:

Generic Name:
tramadol hydrochloride

Trade Name:
Ultram ® [Ortho-McNeil]

IUPAC Name:
(1R,2R)-2-(dimethylaminomethyl)-1-
(3-methoxyphenyl)cyclohexan-1-ol
hydrochloride

Dosage Forms/Routes:
tablet/oral;
extended release tablet/oral;
orally disintegrating tablet/oral;

Major Metabolites:
O-desmethyltramadol;
N-desmethyltramadol

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials]
[PubChem]
[PDSP K_i database]

Initial Approval:
03/03/1995

Manufacturers:
[FDA Search]

Prescribing
Information:
[Link] (Ultram)

[Link] (Ultram ER)

RxList:
[Link]

Empirical Formula:
C₁₆H₂₆ClNO₂

Molecular Mass:
299.836 g/mol

Possible Mechanisms of Action:
Tramadol is a weak agonist at mu opioid receptors (32). A metabolite of tramadol, O-desmethyltramadol, is a more potent mu opioid agonist than its parent drug (33). In addition, tramadol inhibits the reuptake of norepinephrine and serotonin (32). Tramadol may also induce the efflux of serotonin from the serotonin transporter (34) and norepinephrine from the norepinephrine transporter (35). Finally, the metabolite O-desmethyltramadol may act as an antagonist at serotonin 5-HT2C receptors (36).

Indications:
Ultram (tramadol hydrochloride) is indicated for the management of moderate to moderately severe pain in adults.

Ultram ER is indicated for the management of moderate to moderately severe chronic pain in adults who require around-the-clock treatment of their pain for an extended period of time.

Chemical Class:
cyclohexanol derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link]