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

General Information of Drug (ID: DR1112)
Drug Name
Morphine
Synonyms
Meconium; Morfina; Morfina [Italian]; Morphia; Morphin; Morphin [German]; Morphina; Morphina [Italian]; Morphine [BAN]; Morphinism; Morphinum; Morphium; Morpho; Moscontin; Ms Emma; Nepenthe; Oramorph SR; Ospalivina; Roxanol; Statex SR; Astramorph PF; Avinza; Cube juice; DepoDur; Dolcontin; Dreamer; Dulcontin; Duramorph; Duramorph PF; Duromorph; Hard stuff; Infumorph; Kadian; M-Eslon; MORPHINE SULFATE; MS Contin; l-Morphine; morphine; (-)-Morphine; 57-27-2; CCRIS 5762; HSDB 2134; Hocus; Unkie
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 285.34 Topological Polar Surface Area 52.9
Heavy Atom Count 21 Rotatable Bond Count 0
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5288826
PubChem SID
4681 ; 597738 ; 841232 ; 7888991 ; 7980017 ; 8017560 ; 8144201 ; 11041479 ; 14775492 ; 14897787 ; 39321145 ; 46394454 ; 46505161 ; 48416295 ; 49992759 ; 53788344 ; 56312319 ; 56312595 ; 56313877 ; 57359248 ; 79236356 ; 87544101 ; 93166305 ; 96024921 ; 103169185 ; 103914789 ; 126677732 ; 127553079 ; 127829358 ; 134337399 ; 134970862 ; 135650624 ; 137003124 ; 137178956 ; 139157571 ; 152105973 ; 160963643 ; 175268905 ; 175442171 ; 179150686 ; 223674390 ; 223677431 ; 223738295 ; 226395290 ; 241102130
ChEBI ID
ChEBI:17303
CAS Number
57-27-2
TTD Drug ID
D0WE3O
Formula
C17H19NO3
Canonical SMILES
CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)O
InChI
1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1
InChIKey
BQJCRHHNABKAKU-KBQPJGBKSA-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 DM003212
5284371
Conjugation - Methylationn 1 [11]
Morphine ethereal sulfate DM003213 N. A. Conjugation - Sulfation 1 [11]
Morphine glucuronide DM003209
5360621
Conjugation - Glucuronidation 1 [6] , [7] , [8]
Morphine-3-glucuronide DM003210 N. A. Conjugation - Glucuronidation 1 [7] , [6] , [12]
Normorphine DM003211
5462508
Oxidation - Demethylation 1 [11]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004804 Morphine Morphine glucuronide Conjugation - Glucuronidation UGT2B7 ... [6], [7], [8]
MR004805 Morphine Morphine-3-glucuronide Conjugation - Glucuronidation UGT2B7 ... [7], [6], [12]
MR004806 Morphine Normorphine Oxidation - Demethylation Unclear [11]
MR004807 Morphine Codeine Conjugation - Methylationn Unclear [11]
MR004808 Morphine Morphine ethereal sulfate Conjugation - Sulfation Unclear [11]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[6] , [7] , [8]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[9]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[6] , [7] , [8]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[6] , [7] , [8]
UDP-glucuronosyltransferase 2B15 (UGT2B15) DME0049 Homo sapiens
UDB15_HUMAN
2.4.1.17
[6] , [7] , [8]
UDP-glucuronosyltransferase 2B4 (UGT2B4) DME0047 Homo sapiens
UD2B4_HUMAN
2.4.1.17
[6] , [7] , [8]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[10]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[6] , [7] , [8]
⏷ Show the Full List of 12  DME(s)
References
1 Morphine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro metabolism study of buprenorphine: evidence for new metabolic pathways. Drug Metab Dispos. 2005 May;33(5):689-95.
3 Activation of G-proteins by morphine and codeine congeners: insights to the relevance of O- and N-demethylated metabolites at mu- and delta-opioid receptors. J Pharmacol Exp Ther. 2004 Feb;308(2):547-54.
4 Modulation of UDP-glucuronosyltransferase 2B7 function by cytochrome P450s in vitro: differential effects of CYP1A2, CYP2C9 and CYP3A4. Biol Pharm Bull. 2005 Oct;28(10):2026-7.
5 Contribution of UDP-glucuronosyltransferase 1A1 and 1A8 to morphine-6-glucuronidation and its kinetic properties. Drug Metab Dispos. 2008 Apr;36(4):688-94.
6 Pharmacogenomics knowledge for personalized medicine Clin Pharmacol Ther. 2012 Oct;92(4):414-7. doi: 10.1038/clpt.2012.96.
7 Metabolism and pharmacokinetics of morphine in neonates: A review
8 Morphine metabolism, transport and brain disposition
9 Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3. Drug Metab Dispos. 1998 Jun;26(6):507-12.
10 Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine. Drug Metab Dispos. 2010 Apr;38(4):545-53.
11 Morphine: pharmacokinetics and clinical practice
12 Presence of morphine metabolites in human cerebrospinal fluid after intracerebroventricular administration of morphine

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