Norbuprenorphine

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Norbuprenorphine
Norbuprenorphine.png
Systematic (IUPAC) name
(5α,6β,14β,18R)-18-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol
Clinical data
Identifiers
78715-23-8
None
PubChem CID 6426801
ChemSpider 4932224
Chemical data
Formula C25H35NO4
413.55 g/mol

Norbuprenorphine is a major active metabolite of the opioid modulator buprenorphine. It is a μ-opioid, δ-opioid, and nociceptin receptor full agonist,[1][2] and a κ-opioid receptor partial agonist.[2] In rats, unlike buprenorphine, norbuprenorphine produces marked respiratory depression but with very little antinociceptive effect.[3] In explanation of these properties, norbuprenorphine has been found to be a high affinity P-glycoprotein substrate, and in accordance, shows very limited blood-brain-barrier penetration.[3]

See also[edit]

References[edit]

  1. ^ Yassen A, Kan J, Olofsen E, Suidgeest E, Dahan A, Danhof M (May 2007). "Pharmacokinetic-pharmacodynamic modeling of the respiratory depressant effect of norbuprenorphine in rats". The Journal of Pharmacology and Experimental Therapeutics 321 (2): 598–607. doi:10.1124/jpet.106.115972. PMID 17283225. 
  2. ^ a b Huang P, Kehner GB, Cowan A, Liu-Chen LY (May 2001). "Comparison of pharmacological activities of buprenorphine and norbuprenorphine: norbuprenorphine is a potent opioid agonist". The Journal of Pharmacology and Experimental Therapeutics 297 (2): 688–95. PMID 11303059. 
  3. ^ a b Brown SM, Campbell SD, Crafford A, Regina KJ, Holtzman MJ, Kharasch ED (October 2012). "P-glycoprotein is a major determinant of norbuprenorphine brain exposure and antinociception". J. Pharmacol. Exp. Ther. 343 (1): 53–61. doi:10.1124/jpet.112.193433. PMC 3464040. PMID 22739506.