Codeine-6-glucuronide

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Active metabolite of codeine

title: "Codeine-6-glucuronide" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["mu-opioid-receptor-agonists", "4,5-epoxymorphinans", "opioid-metabolites", "glucuronides", "hydroxyarenes"] description: "Active metabolite of codeine" topic_path: "general/mu-opioid-receptor-agonists" source: "https://en.wikipedia.org/wiki/Codeine-6-glucuronide" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Active metabolite of codeine ::

| ImageFile = Codeine-6-glucuronide.svg | ImageClass = skin-invert-image | ImageSize = 200px | IUPACName = (5α,6α)-3-methoxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-yl β-D-glucopyranosiduronic acid | PIN = (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 | OtherNames = |Section1={{Chembox Identifiers | CASNo = 20736-11-2 | CASNo_Ref = | UNII_Ref = | UNII = E2M937KY47 | PubChem = 5489029 | ChemSpiderID = 4590054 | SMILES = O=C(O)[C@H]6OC@@H C@H C@@H[C@@H]6O | StdInChI = 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 | StdInChIKey = CRWVOYRJXPDBPM-HSCJLHHPSA-N |Section2={{Chembox Properties | C=24 | H=29 | N=1 | O=9 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

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. During its metabolism, codeine is conjugated with glucuronic acid by the enzyme UDP-Glucuronosyltransferase-2B7 (UGT2B7) to form codeine-6-glucuronide.{{Cite journal | last1 = Vree | first1 = T. B. | last2 = Van Dongen | first2 = R. T. | last3 = Koopman-Kimenai | first3 = P. M. | title = Codeine analgesia is due to codeine-6-glucuronide, not morphine | journal = International Journal of Clinical Practice | volume = 54 | issue = 6 | pages = 395–398 | year = 2000 | doi = 10.1111/j.1742-1241.2000.tb11929.x | pmid = 11092114 | s2cid = 8281493 | last1 = Armstrong | first1 = S. C. | last2 = Cozza | first2 = K. L. | doi = 10.1176/appi.psy.44.6.515 | title = Pharmacokinetic Drug Interactions of Morphine, Codeine, and Their Derivatives: Theory and Clinical Reality, Part II | journal = Psychosomatics | volume = 44 | issue = 6 | pages = 515–520 | year = 2003 | pmid = 14597688 | pmc = | doi-access = free

References

(1997). "Analgesic effects of codeine-6-glucuronide after intravenous administration". European Journal of Pain.

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