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.
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CYP3A |
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CYP3A4 |
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CYP3A5 |
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UGT1A1 |
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UGT1A3 |
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UGT2B7 |
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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.
LinkOuts
Common Searches
Search PubMed
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.