Buprenorphine-3-glucuronide
 | |
| Systematic (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 | |
| Identifiers | |
| CAS Number | 101224-22-0 |
| ATC code | None |
| PubChem | CID 127780 |
| ChemSpider | 113341 |
| Chemical data | |
| Formula | C35H49NO10 |
| Molar mass | 643.764 g/mol |
| |
| |
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]
See also
References
- 1 2 3 4 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.
- 1 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.