Drug/Small Molecule:
buprenorphine

2D structure

Overview

Generic Names: Buprenophine; Buprenorfina [INN-Spanish]; Buprenorphine Hcl; Buprenorphinum [INN-Latin]; buprenorphine
Trade Names: Buprel; Buprenex; Probuphine; Subutex; Temgesic
PharmGKB Accession Id: PA448685

Description

A derivative of the opioid alkaloid thebaine that is a more potent and longer lasting analgesic than morphine. It appears to act as a partial agonist at mu and kappa opioid receptors and as an antagonist at delta receptors. The lack of delta-agonist activity has been suggested to account for the observation that buprenorphine tolerance may not develop with chronic use. [PubChem]

Indication

For the treatment of moderate to severe pain, peri-operative analgesia, and opioid dependence.

ATC Therapeutic Categories

  • N02AE:Oripavine derivatives
  • N07BC:Drugs used in opioid dependence

Pharmacology and Interactions

Mechanism Of Action

Buprenorphine's analgesic effect is due to partial agonist activity at mu-opioid receptors. Buprenorphine is also a kappa-opioid receptor antagonist. The partial agonist activity means that opioid receptor antagonists (e.g., an antidote such as naloxone) only partially reverse the effects of buprenorphine. The binding to the mu and kappa receptors results in hyperpolarization and reduced neuronal excitability.

Pharmacology

Buprenorphine is a synthetic opioid analgesic and thebaine derivative, with a longer duration of action than morphine. Buprenorphine interacts predominately with the opioid mu-receptor. These mu-binding sites are discretely distributed in the human brain, spinal cord, and other tissues. In clinical settings, buprenorphine exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Buprenorphine may increase the patient's tolerance for pain and decrease the perception of suffering, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Buprenorphine depresses the respiratory centers, depresses the cough reflex, and constricts the pupils.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic. Buprenorphine undergoes both N-dealkylation to norbuprenorphine and glucuronidation. The N-dealkylation pathway is mediated by cytochrome P-450 3A4 isozyme. Norbuprenorphine, an active metabolite, can further undergo glucuronidation.

Protein Binding

96%

Absorption

31% bioavailability (sublingual)

Half Life

37 hours

Toxicity

Manifestations of acute overdose include pinpoint pupils, sedation, hypotension, respiratory depression and death.

Chemical Properties

Chemical Formula:

C29H41NO4

SMILES Code:

CC(C)(C)C(C)([C@H]1C[C@@]23CC[C@]1(C4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

467.6401 / 467.3036

Curated Information

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Not annotated
CYP3A
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Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP3A4
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Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP3A5
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Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
UGT1A1
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Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
UGT1A3
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Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
UGT2B7
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  • PK
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Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Metabolizing Enzymes

Drug Targets

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. Physicochemical determinants of human renal clearance

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00921
KEGG Compound ID:
C08007
PubChem Compound ID:
40400
PubChem Substance ID:
181274

Common Searches

Search PubMed
Search Medline Plus
Search PubChem
Search CTD

Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
The PharmGKB is financially supported by the NIH/ NIGMS and is managed at Stanford University (U01GM61374).
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