Codeine-6-glucuronide
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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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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]
Formation
[edit]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]
See also
[edit]References
[edit]- ↑ Srinivasan, V.; Wielbo, D.; Tebbett, I. R. (1997). "Analgesic effects of codeine-6-glucuronide after intravenous administration". European Journal of Pain. 1 (3): 185–190. doi:10.1016/S1090-3801(97)90103-8. PMID 15102399. S2CID 23099329.
- ↑ Vree, TB; Van Dongen, RTM; Koopman-Kimenai, PM (2000). "Codeine Analgesia is Due to Codeine-6-Glucuronide, Not Morphine". International Journal of Clinical Practice. 54 (6): 395–398. doi:10.1111/j.1742-1241.2000.tb11929.x. PMID 11092114.
- ↑ Armstrong, Scott C.; Cozza, Kelly L. (2003). "Pharmacokinetic Drug Interactions of Morphine, Codeine, and Their Derivatives: Theory and Clinical Reality, Part II". Psychosomatics. 44 (6): 515–520. doi:10.1176/appi.psy.44.6.515. PMID 14597688.