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Codeine-6-glucuronide
Names
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)
ChemSpider
UNII
  • 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
  • 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
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).

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

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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]

2D representation of the chemical structure of codeine .
codeine
+ UDP-glucuronate
 
 
 
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of codeine-6-glucuronide .
codeine-6-glucuronide


See also

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References

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  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, 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.
  3. ^ 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.

📚 Artikel Terkait di Wikipedia

Morphine-6-glucuronide

byproduct: morphine + UDP-glucuronate       UDP       morphine-6-glucuronide Codeine-6-glucuronide Morphine-N-oxide Coffman BL, Rios GR, King CD, Tephly TR

Codeine

useful in treating codeine dependence, though the metabolism of codeine to morphine (and hence further metabolism to glucuronide morphine conjugates)

Glucuronidation

mouse liver. The substances resulting from glucuronidation are known as glucuronides (or glucuronosides) and are typically much more water-soluble than the

Toxication

toxicological activity. Codeine is an example of a prodrug, metabolized in the body to the active compounds morphine and codeine-6-glucuronide. Phase I of drug

List of opioids

Structures Codeine-6-glucuronide  Codeine-N-oxide (genocodeine)[18] Heroin-7,8-oxide [19] Morphine-6-glucuronide 3-Monoacetylmorphine 6-Monoacetylmorphine

Codeine/paracetamol

Codeine/paracetamol, also called codeine/acetaminophen and co-codamol, is a compound analgesic, comprising codeine phosphate and paracetamol (acetaminophen)

Equianalgesic

2010). "Pharmacokinetics of acetaminophen, codeine, and the codeine metabolites morphine and codeine-6-glucuronide in healthy Greyhound dogs". J. Vet. Pharmacol

Lean (drug)

popular in hip hop culture, especially within the Southern United States. Codeine/promethazine syrup is usually used to make lean, but other syrups are also