codeine-6-glucuronide

{{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 = (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 = {{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.{{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 }} 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

}}{{Cite journal

| 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

}}