Codeine-6-glucuronide
Active metabolite of codeine
From Wikipedia, the free encyclopedia
Codeine-6-glucuronide (C6G) is a major active metabolite of codeine and may be responsible for as much as 60% of the analgesic effects of codeine. C6G exhibits decreased immunosuppressive effects compared to codeine.[1]
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| Names | |
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| IUPAC name
(5α,6α)-3-methoxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-yl β-D-glucopyranosiduronic acid | |
| Preferred IUPAC name
(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-{[(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinolin-7-yl]oxy}oxane-2-carboxylic acid | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C24H29NO9 | |
| Molar mass | 475.494 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Formation
A glucuronosyltransferase enzyme UGT2B7 present in human liver converts codeine to its glucuronide by adding a sugar acid at the hydroxy group, with uridine diphosphate (UDP) as byproduct:[2][3]
