{{Short description|Active metabolite of codeine}} {{Chembox | 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 = (2''S'',3''S'',4''S'',5''R'',6''R'')-3,4,5-Trihydroxy-6-<nowiki/>{[(4''R'',4a''R'',7''S'',7a''R'',12b''S'')-9-methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1''H''-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 = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = E2M937KY47 | PubChem = 5489029 | ChemSpiderID = 4590054 | 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 | 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.<ref>{{Cite journal | last1 = Srinivasan | first1 = V. | last2 = Wielbo | first2 = D. | last3 = Tebbett | first3 = I. R. | title = Analgesic effects of codeine-6-glucuronide after intravenous administration | journal = European Journal of Pain | volume = 1 | issue = 3 | pages = 185–190 | year = 1997 | pmid = 15102399 | doi = 10.1016/S1090-3801(97)90103-8| s2cid = 23099329 }}</ref>
==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:<ref>{{cite journal |last1=Vree |first1=TB |last2=Van Dongen |first2=RTM |last3=Koopman-Kimenai |first3=PM |title=Codeine Analgesia is Due to Codeine-6-Glucuronide, Not Morphine |journal=International Journal of Clinical Practice |date=2000 |volume=54 |issue=6 |pages=395–398 |doi=10.1111/j.1742-1241.2000.tb11929.x |pmid=11092114 }} </ref><ref>{{cite journal |last1=Armstrong |first1=Scott C. |last2=Cozza |first2=Kelly L. |title=Pharmacokinetic Drug Interactions of Morphine, Codeine, and Their Derivatives: Theory and Clinical Reality, Part II |journal=Psychosomatics |date=2003 |volume=44 |issue=6 |pages=515–520 |doi=10.1176/appi.psy.44.6.515 |doi-access=free |pmid=14597688 }}</ref>
{{chemrxn|width=65%| {{chemrxn/cpd|codeine }} {{chemrxn/txt|+ UDP-glucuronate }} {{chemrxn/arw|fwd_out=UDP }} {{chemrxn/cpd|codeine-6-glucuronide }} }}
==See also== * Morphine-6-glucuronide
==References== {{Reflist|2}}
{{Opioidergics}}
Category:Mu-opioid receptor agonists Category:4,5-Epoxymorphinans Category:Opioid metabolites Category:Glucuronides Category:Hydroxyarenes