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Buprenorphine-3-glucuronide

August 25, 2023

Buprenorphine-3-glucuronide (B3G) is a major active metabolite of the opioid modulator buprenorphine.[1] It has affinity for the μ-opioid receptor (Ki = 4.9 (± 2.7) pM), δ-opioid receptor (Ki = 270 nM), and nociceptin receptor (Ki = 36 μM), but not for the κ-opioid receptor.[1] Whether B3G acts as an agonist or antagonist of 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 of antinociception, and similarly to buprenorphine in these assays, has not been found to produce sedation, reduce locomotion, or decrease respiratory rate.[1] Of all of the active metabolites of buprenorphine, B3G is thought to be the most similar to the parent drug.[1] Unlike norbuprenorphine, but similarly to buprenorphine (and norbuprenorphine-3-glucuronide), B3G is not a substrate for P-glycoprotein, and hence may cross the blood-brain-barrier significantly.[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
  • 101224-22-0 Y
PubChem CID
  • 127780
ChemSpider
  • 113341
UNII
  • L7FYM9GI97
CompTox Dashboard (EPA)
  • DTXSID40906012
Chemical and physical data
FormulaC35H49NO10
Molar mass643.774 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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 Edit

References Edit

  1. ^ a b c d Brown 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. PMC 3560935. PMID 22037640.
  2. ^ 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.


 

This analgesic-related article is a stub. You can help Wikipedia by expanding it.

August 25, 2023
buprenorphine, glucuronide, major, active, metabolite, opioid, modulator, buprenorphine, affinity, opioid, receptor, opioid, receptor, nociceptin, receptor, opioid, receptor, whether, acts, agonist, antagonist, each, former, three, respective, sites, determine. Buprenorphine 3 glucuronide B3G is a major active metabolite of the opioid modulator buprenorphine 1 It has affinity for the m opioid receptor Ki 4 9 2 7 pM d opioid receptor Ki 270 nM and nociceptin receptor Ki 36 mM but not for the k opioid receptor 1 Whether B3G acts as an agonist or antagonist of 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 of antinociception and similarly to buprenorphine in these assays has not been found to produce sedation reduce locomotion or decrease respiratory rate 1 Of all of the active metabolites of buprenorphine B3G is thought to be the most similar to the parent drug 1 Unlike norbuprenorphine but similarly to buprenorphine and norbuprenorphine 3 glucuronide B3G is not a substrate for P glycoprotein and hence may cross the blood brain barrier significantly 2 Buprenorphine 3 glucuronideClinical dataATC codeNoneIdentifiersIUPAC name 5a 6b 14b 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 b D glucopyranosiduronic acidCAS Number101224 22 0 YPubChem CID127780ChemSpider113341UNIIL7FYM9GI97CompTox Dashboard EPA DTXSID40906012Chemical and physical dataFormulaC 35H 49N O 10Molar mass643 774 g mol 13D model JSmol Interactive imageSMILES 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 OInChI 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 s1Key CZULHKGIAJASAA WWIHBJMFSA NSee also EditMorphine 3 glucuronideReferences Edit a b c d Brown 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 PMC 3560935 PMID 22037640 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 This analgesic related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Buprenorphine 3 glucuronide amp oldid 1090160224, wikipedia, wiki, book, books, library,

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