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Buprenorphine

Catalog No. DB00921 Name DrugBank
CAS Number 52485-79-7 Website http://www.ualberta.ca/
M. F. C29H41NO4 Telephone (780) 492-3111
M. W. 467.64014 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 797

SYNONYMS

IUPAC name
(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11-trien-11-ol
IUPAC Traditional name
buprenorphine hydrochloride
Brand Name
Probuphine
Buprel
Subutex
Buprenex
Temgesic
Synonyms
Buprenorphinum [INN-Latin]
Buprenorfina [INN-Spanish]
Buprenophine
Buprenorphine Hcl
buprenorphine

DATABASE IDS

PubChem CID 40400
CAS Number 52485-79-7
PubChem SID 46505782

PROPERTIES

Hydrophobicity(logP) 3.8

DETAILS

Description (English)
Item Information
Drug Groups illicit; approved; investigational
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.
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.
Toxicity Manifestations of acute overdose include pinpoint pupils, sedation, hypotension, respiratory depression and death.
Affected Organisms
Humans and other mammals
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.
Absorption 31% bioavailability (sublingual)
Half Life 37 hours
Protein Binding 96%
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.
References
Huang P, Kehner GB, Cowan A, Liu-Chen LY: Comparison of pharmacological activities of buprenorphine and norbuprenorphine: norbuprenorphine is a potent opioid agonist. J Pharmacol Exp Ther. 2001 May;297(2):688-95. [Pubmed]
Bodkin JA, Zornberg GL, Lukas SE, Cole JO: Buprenorphine treatment of refractory depression. J Clin Psychopharmacol. 1995 Feb;15(1):49-57. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

  • Huang P, Kehner GB, Cowan A, Liu-Chen LY: Comparison of pharmacological activities of buprenorphine and norbuprenorphine: norbuprenorphine is a potent opioid agonist. J Pharmacol Exp Ther. 2001 May;297(2):688-95. Pubmed
  • Bodkin JA, Zornberg GL, Lukas SE, Cole JO: Buprenorphine treatment of refractory depression. J Clin Psychopharmacol. 1995 Feb;15(1):49-57. Pubmed