Buprenorphine-3-glucuronide

Buprenorphine-3-glucuronide (B3G) is a major active metabolite of the opioid modulator buprenorphine.^[1] It has affinity for the μ-opioid receptor (K_i = 4.9 (± 2.7) pM), δ-opioid receptor (K_i = 270 nM), and nociceptin receptor (K_i = 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
IUPAC name (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
Formula	C35H49NO10
Molar mass	643.774 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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

• Morphine-3-glucuronide

References

1. 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. 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.