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QuickView for Buprenorphine (compound)

Summary
General Info

PubChem

PubChem Compound 11969480

PubChem Compound 11969480

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. show more » 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; CL 112302; EINECS 258-396-8; 52485-79-7; 53152-21-9; UM 952; 55327-62-3; CL 112,302; Subutex; Buprenorphine hydrochloride; 53187-13-6; MR 56 show less «

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... show more » 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. show less «
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 ... show more » 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. show less «
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:

Triprolidine	The CNS depressants, Triprolidine and Buprenorphine, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Procarbazine	Buprenorphine 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.
Linezolid	Buprenorphine 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.
Rasagiline	Buprenorphine 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.
Atazanavir	Atazanavir 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.

Triprolidine	The CNS depressants, Triprolidine and Buprenorphine, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
Procarbazine	Buprenorphine 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.
Linezolid	Buprenorphine 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.
Rasagiline	Buprenorphine 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.
Atazanavir	Atazanavir 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.
Droperidol	Droperidol may enhance the CNS depressant effect of CNS Depressants like buprenorphine. Consider dose reductions of droperidol or of other CNS agents (e.g., opioids, barbiturates) with concomitant use.
Selegiline	Buprenorphine may enhance the adverse/toxic effect of MAO Inhibitors like selegiline. 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.
Tranylcypromine	Buprenorphine may enhance the adverse/toxic effect of MAO Inhibitors like tranylcypromine. 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.
Moclobemide	Buprenorphine may enhance the adverse/toxic effect of MAO Inhibitors like moclobemide. 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.
Telithromycin	Telithromycin may reduce clearance of Buprenorphine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Buprenorphine if Telithromycin is initiated, discontinued or dose changed.
Phenelzine	Buprenorphine may enhance the adverse/toxic effect of MAO Inhibitors like phenelzine. 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.
Conivaptan	Conivaptan may increase the serum concentration of CYP3A4 Substrates like buprenorphine. Upon completion/discontinuation of conivaptan, allow at least 7 days before initiating therapy with drugs that are CYP3A4 substrates.
Isocarboxazid	Buprenorphine may enhance the adverse/toxic effect of MAO Inhibitors like isocarboxazid. 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.
Alvimopan	Opioids like buprenorphine may enhance the adverse/toxic effect of Alvimopan. This is most notable for patients receiving long-term (i.e., more than 7 days) opiates prior to alvimopan initiation. Consider therapy modification.
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of buprenorphine by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of buprenorphine if voriconazole is initiated, discontinued or dose changed.

Targets

Mu-type opioid receptor

Kappa-type opioid receptor

Delta-type opioid receptor

Enzymes

Cytochrome P450 3A4

Cytochrome P450 3A5

Cytochrome P450 2C9

Cytochrome P450 2C8

Cytochrome P450 3A7

UDP-glucuronosyltransferase 1-9

Cytochrome P450 2D6

Cytochrome P450 2C18

Cytochrome P450 2C19

Cytochrome P450 1A2

Cytochrome P450 2A6

Transporters

Multidrug resistance protein 1

ATP-binding cassette sub-family G member 2