Codeine-6-glucuronide

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] During its metabolism, codeine is conjugated with glucuronic acid by the enzyme UDP-Glucuronosyltransferase-2B7 (UGT2B7) to form codeine-6-glucuronide.[2][3]

Codeine-6-glucuronide

Names
IUPAC name (5α,6α)-3-methoxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-yl β-D-glucopyranosiduronic acid
Identifiers
3D model (JSmol)	Interactive image
ChemSpider	4590054
PubChem CID	5489029
CompTox Dashboard (EPA)	DTXSID60942952
InChI InChI=1S/C24H29NO9/c1-25-8-7-24-11-4-6-14(32-23-18(28)16(26)17(27)20(34-23)22(29)30)21(24)33-19-13(31-2)5-3-10(15(19)24)9-12(11)25/h3-6,11-12,14,16-18,20-21,23,26-28H,7-9H2,1-2H3,(H,29,30)/t11-,12+,14-,16-,17-,18+,20-,21-,23+,24-/m0/s1 Key: CRWVOYRJXPDBPM-HSCJLHHPSA-N InChI=1/C24H29NO9/c1-25-8-7-24-11-4-6-14(32-23-18(28)16(26)17(27)20(34-23)22(29)30)21(24)33-19-13(31-2)5-3-10(15(19)24)9-12(11)25/h3-6,11-12,14,16-18,20-21,23,26-28H,7-9H2,1-2H3,(H,29,30)/t11-,12+,14-,16-,17-,18+,20-,21-,23+,24-/m0/s1 Key: CRWVOYRJXPDBPM-HSCJLHHPBJ
SMILES O=C(O)[C@H]6O[C@@H](O[C@H]1/C=C\[C@@H]5[C@@]24c3c(ccc(OC)c3O[C@@H]12)C[C@H]5N(C)CC4)[C@H](O)[C@@H](O)[C@@H]6O
Properties
Chemical formula	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).
Infobox references

See also

• Morphine-6-glucuronide

References

1. 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.
2. Vree, T. B.; Van Dongen, R. T.; Koopman-Kimenai, P. M. (2000). "Codeine analgesia is due to codeine-6-glucuronide, not morphine". International Journal of Clinical Practice. 54 (6): 395–398. PMID 11092114.
3. Armstrong, S. C.; Cozza, K. 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.