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Norbuprenorphine

From Wikipedia, the free encyclopedia
Active metabolite of buprenorphine
Pharmaceutical compound
Norbuprenorphine
Clinical data
ATC code
  • None
Identifiers
  • (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
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.208.387Edit this at Wikidata
Chemical and physical data
FormulaC25H35NO4
Molar mass413.558 g·mol−1
3D model (JSmol)
  • C[C@]([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN[C@@H]3Cc6c5c(c(cc6)O)O4)OC)(C(C)(C)C)O
  • InChI=1S/C25H35NO4/c1-21(2,3)22(4,28)16-13-23-8-9-25(16,29-5)20-24(23)10-11-26-17(23)12-14-6-7-15(27)19(30-20)18(14)24/h6-7,16-17,20,26-28H,8-13H2,1-5H3/t16-,17-,20-,22+,23-,24+,25-/m1/s1
  • Key:YOYLLRBMGQRFTN-IOMBULRVSA-N

Norbuprenorphine is a majoractive metabolite of theopioid modulatorbuprenorphine. It is aμ-opioid,δ-opioid, andnociceptin receptorfull agonist,[1][2] and aκ-opioid receptorpartial agonist.[2] In rats, unlike buprenorphine, norbuprenorphine produces markedrespiratory depression but with very littleantinociceptive effect.[3] In explanation of these properties, norbuprenorphine has been found to be a high affinityP-glycoproteinsubstrate, and in accordance, shows very limitedblood-brain-barrier penetration.[3]

Norbuprenorphine

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.S2CID 11921738.
  2. ^abHuang 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.doi:10.1016/S0022-3565(24)29586-0.PMID 11303059.
  3. ^abBrown 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.
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
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