Wikipedia

Buprenorphine-3-glucuronide

Buprenorphine-3-glucuronide(B3G) is a majoractive metaboliteof theopioid modulatorbuprenorphine.[1]It hasaffinityfor theμ-opioid receptor(Ki= 4.9 (± 2.7) pM),δ-opioid receptor(Ki= 270 nM), andnociceptin receptor(Ki= 36 μM), but not for theκ-opioid receptor.[1]Whether B3G acts as anagonistorantagonistof each of the former three respective sites has yet to be determined.[2]In rats, at the doses assayed, B3G has been found to produce a small degree ofantinociception,and similarly to buprenorphine in these assays, has not been found to producesedation,reducelocomotion,or decreaserespiratory rate.[1]Of all of the active metabolites of buprenorphine, B3G is thought to be the most similar to the parent drug.[1]Unlikenorbuprenorphine,but similarly to buprenorphine (andnorbuprenorphine-3-glucuronide), B3G is not asubstrateforP-glycoprotein,and hence may cross theblood-brain-barriersignificantly.[2]

Buprenorphine-3-glucuronide
Clinical data
ATC code
  • None
Identifiers
  • (5α,6β,14β,18R)-17-(Cyclopropylmethyl)-18-[(2S)-2-hydroxy-3,3-dimethyl-2-butanyl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-2-yl β-D-glucopyranosiduronic acid
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC35H49NO10
Molar mass643.774g·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[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O)O4)CC8CC8)OC)(C(C)(C)C)O
  • InChI=1S/C35H49NO10/c1-31(2,3)32(4,42)20-15-33-10-11-35(20,43-5)30-34(33)12-13-36(16-17-6-7-17)21(33)14-18-8-9-19(26(46-30)22(18)34)44-29-25(39)23(37)24(38)27(45-29)28(40)41/h8-9,17,20-21,23-25,27,29-30,37-39,42H,6-7,10-16H2,1-5H3,(H,40,41)/t20-,21-,23+,24+,25-,27+,29-,30-,32+,33-,34+,35-/m1/s1
  • Key:CZULHKGIAJASAA-WWIHBJMFSA-N

See also

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References

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  1. ^abcdBrown SM, Holtzman M, Kim T, Kharasch ED (December 2011)."Buprenorphine metabolites, buprenorphine-3-glucuronide and norbuprenorphine-3-glucuronide, are biologically active".Anesthesiology.115(6): 1251–60.doi:10.1097/ALN.0b013e318238fea0.PMC3560935.PMID22037640.
  2. ^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.PMC3464040.PMID22739506.

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