Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0366)
Drug Name
Codeine
Prodrug Info Codeine is the prodrug of Morphine
Synonyms
Codein; Codeine Anhydrate; Codeine anhydrous; Codeine polistirex; Codicept; Coducept; Methylmorphine; Morphine 3-methyl ether; CODEINE BASE; Morphine monomethyl ether; Morphine-3-methyl ester; Morphine-3-methyl ether; Norcodeine, N-methyl; Norcodine, N-methyl; O(3)-methylmorphine; O3-Methylmorphine; UX6OWY2V7J; codeina; codeine; codeinum; l-Codeine; (-)-Codeine; 76-57-3; CCRIS 7555; CHEBI:16714; EINECS 200-969-1; HSDB 3043; Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-; UNII-UX6OWY2V7J
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 299.4 Topological Polar Surface Area 41.9
Heavy Atom Count 22 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5284371
PubChem SID
8425 ; 841961 ; 7978983 ; 8144934 ; 11039235 ; 14825207 ; 15419416 ; 24892429 ; 24892819 ; 28325869 ; 39317728 ; 46507764 ; 48413480 ; 48415816 ; 48423163 ; 49855816 ; 50881119 ; 53788605 ; 57653987 ; 57654027 ; 87544102 ; 92710514 ; 103169342 ; 103930322 ; 104000895 ; 117497011 ; 124954734 ; 126631803 ; 126678046 ; 128851630 ; 134337528 ; 134971680 ; 135650117 ; 137001257 ; 137175320 ; 142842434 ; 144207280 ; 152094958 ; 160963666 ; 164838528 ; 175268396 ; 175442317 ; 179151116 ; 223554832 ; 223680835 ; 223739746 ; 226395484 ; 241129665
ChEBI ID
ChEBI:16714
CAS Number
76-57-3
TTD Drug ID
D03DIG
Formula
C18H21NO3
Canonical SMILES
CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O
InChI
1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
InChIKey
OROGSEYTTFOCAN-DNJOTXNNSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Codeine-6-glucuronide DM003705
5489029
Unclear 1 [8]
Morphine DM003208
60053788
Conjugation - Glucuronidation 1 [9] , [10] , [8]
Norcodeine DM003702
9925873
Oxidation - N-demethylation 1 [8]
Morphine 3 glucuronide DM003703
5484731
Conjugation - Glucuronidation 2 [11]
Morphine glucuronide DM003209
5360621
Unclear 2 [11]
Normorphine DM003211
5462508
Conjugation - Glucuronidation 2 [12]
Normorphine DM003211
5462508
Oxidation - O-demethylation 2 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004094 Codeine Norcodeine Oxidation - N-demethylation CYP3A4 [8]
MR004096 Codeine Morphine Conjugation - Glucuronidation UGT2B7 [9], [10], [8]
MR004100 Codeine Codeine-6-glucuronide Unclear Unclear [8]
MR004097 Morphine Morphine 3 glucuronide Conjugation - Glucuronidation UGT2B7 [11]
MR004098 Morphine Morphine 6 glucuronide Unclear Unclear [11]
MR004099 Morphine Normorphine Conjugation - Glucuronidation UGT2B7 ... [12]
MR004095 Norcodeine Normorphine Oxidation - O-demethylation CYP2D6 [8]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 2B4 (UGT2B4) DME0047 Homo sapiens
UD2B4_HUMAN
2.4.1.17
[6]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[7]
⏷ Show the Full List of 6  DME(s)
References
1 Ibuprofen was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Polymorphism of human cytochrome P450 2D6 and its clinical significance: Part I. Clin Pharmacokinet. 2009;48(11):689-723.
3 Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8.
4 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
5 Evaluation of 3'-azido-3'-deoxythymidine, morphine, and codeine as probe substrates for UDP-glucuronosyltransferase 2B7 (UGT2B7) in human liver microsomes: specificity and influence of the UGT2B7*2 polymorphism. Drug Metab Dispos. 2003 Sep;31(9):1125-33.
6 Methadone inhibits CYP2D6 and UGT2B7/2B4 in vivo: a study using codeine in methadone- and buprenorphine-maintained subjects. Br J Clin Pharmacol. 2012 May;73(5):786-94.
7 Human UGT2B7 catalyzes morphine glucuronidation. Drug Metab Dispos. 1997 Jan;25(1):1-4.
8 Pharmacogenetics of analgesic drugs
9 Microsomal codeine N-demethylation: cosegregation with cytochrome P4503A4 activity
10 Pharmacokinetics and metabolism of codeine in humans
11 DrugBank(Pharmacology-Metabolism):Codeine
12 Diclofenac does not interact with codeine metabolism in vivo: a study in healthy volunteers

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