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