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QuickView for Buprenorphine (compound)


PubChem
Name: Buprenorphine
PubChem Compound ID: 11969480
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.
Molecular formula: C29H42ClNO4
Molecular weight: 504.101 g/mol
Synonyms:
Temgesic; 64425-21-4; 21-Cyclopropyl-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine hydrochloride; Buprenorphine hydrochloride [USAN:JAN]; NIH 8805; (5alpha,7alpha(S))-alpha-tert-Butyl-17-(cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha-methyl-6,14-ethenomorphinan-7-methanol hydrochloride; 6,14-Ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-alpha-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha-methyl-, hydrochloride, (5alpha,7alpha(S))-; Finibron; RX 6029-M; Buprenex.
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DrugBank
Identification
Name: Buprenorphine
Name (isomeric): DB00921
Drug Type: small molecule
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.
Synonyms:
Buprenorfina [INN-Spanish]; Buprenophine; Buprenorphine Hcl; Buprenorphinum [INN-Latin]
Brand: Probuphine, Temgesic, Subutex, Buprel, Buprenex
Category: Narcotic Antagonists, Narcotics, Analgesics, Opioid
CAS number: 52485-79-7
Pharmacology
Indication: For the treatment of moderate to severe pain, peri-operative analgesia, and opioid dependence.
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 pharm...
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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 ...
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Absorption: 31% bioavailability (sublingual)
Protein binding: 96%
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.
Route of elimination: Buprenorphine, in common with morphine and other phenolic opioid analgesics, is metabolized by the liver and its clearance is related to hepatic blood flow.
Half Life: 37 hours
Toxicity: Manifestations of acute overdose include pinpoint pupils, sedation, hypotension, respiratory depression and death.
Affected organisms: Humans and other mammals
Interactions
Drug interaction:
TriprolidineThe CNS depressants, Triprolidine and Buprenorphine, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
ProcarbazineBuprenorphine may enhance the adverse/toxic effect of MAO Inhibitors like procarbazine. When possible, avoid use of buprenorphine in patients who have used a monoamine oxidase inhibitor within the past 14 days due to possible severe adverse effects.
LinezolidBuprenorphine may enhance the adverse/toxic effect of MAO Inhibitors like linezolid. When possible, avoid use of buprenorphine in patients who have used a monoamine oxidase inhibitor within the past 14 days due to possible severe adverse effects.
RasagilineBuprenorphine may enhance the adverse/toxic effect of MAO Inhibitors like rasagiline. When possible, avoid use of buprenorphine in patients who have used a monoamine oxidase inhibitor within the past 14 days due to possible severe adverse effects.
AtazanavirAtazanavir may increase the serum concentration of Buprenorphine. Buprenorphine may decrease the serum concentration of Atazanavir. Avoid use of buprenorphine in patients receiving atazanavir without ritonavir boosting due to possible decreases in atazanavir exposure. In patients receiving buprenorphine with atazanavir/ritonavir, monitor for increased buprenorphine effects and consider dose reductions if patients experience adverse effects.
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