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

General Information of Drug (ID: DR1039)
Drug Name
Methadone
Synonyms
Levometadona; Levometadona [INN-Spanish]; Levomethadone; Levomethadone (INN); Levomethadone [INN]; Levomethadonum; Levomethadonum [INN-Latin]; Levothyl; Polamivet; L-Polamidon; l-Polamivet; (-)-(R)-6-(Dimethylamino)-4,4-diphenyl-3-heptanone; (-)-Methadone; (6R)-Methadone; (R)-6-(Dimethylamino)-4,4-diphenyl-3-heptanone; (R)-Methadone; 125-58-6; 3-HEPTANONE, 6-(DIMETHYLAMINO)-4,4-DIPHENYL-, L-; 3-Hetpanone, 6-(dimethylamino)-4,4-diphenyl-, (R)- (9CI); 6Y75Z4E8NS; L-6-(Dimethylamino)-4,4-diphenyl-3-heptanone; UNII-6Y75Z4E8NS
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 309.4 Topological Polar Surface Area 20.3
Heavy Atom Count 23 Rotatable Bond Count 7
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
22267
PubChem SID
841133 ; 8166385 ; 16828013 ; 29289580 ; 47359869 ; 47510027 ; 50251534 ; 57331123 ; 93167208 ; 96024811 ; 103412836 ; 104355526 ; 129415111 ; 131326064 ; 135650582 ; 138237674 ; 141601059 ; 144239892 ; 162222373 ; 175271129 ; 198945476 ; 226513694
ChEBI ID
ChEBI:6807
CAS Number
76-99-3
TTD Drug ID
D09OJQ
Formula
C21H27NO
Canonical SMILES
CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2
InChI
1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3/t17-/m1/s1
InChIKey
USSIQXCVUWKGNF-QGZVFWFLSA-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
4-dimethylamino-22-diphenylvaleric acid DM018107 N. A. Unclear - Unclear 1 [5] , [3]
EDDP DM015453
5378015
Oxidation - N-demethylation 1 [5] , [3]
Methadol DM015001
28397
Unclear - Unclear 1 [5] , [3]
4-methylamino-2,2-diphenylvaleric acid DM018108 N. A. Unclear - Unclear 2 [5] , [3]
EMDP DM015551
9879368
Oxidation - N-Demethylization 2 [5] , [3]
Normethadol DM015182
135027
Unclear - Unclear 2 [5] , [3]
15-dimethyi-33-diphenyl-2-pyrrolidone DM018109 N. A. Unclear - Unclear 3 [5] , [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009993 Methadone 4-dimethylamino-22-diphenylvaleric acid Unclear - Unclear Unclear [5], [3]
MR009996 Methadone Methadol Unclear - Unclear ADH [5], [3]
MR009998 Methadone EDDP Oxidation - N-demethylation CYP1A2 ... [5], [3]
MR009994 4-dimethylamino-22-diphenylvaleric acid 4-methylamino-2,2-diphenylvaleric acid Unclear - Unclear Unclear [5], [3]
MR009999 EDDP EMDP Oxidation - N-Demethylization CYP [5], [3]
MR009997 Methadol Normethadol Unclear - Unclear CYP [5], [3]
MR009995 4-methylamino-2,2-diphenylvaleric acid 15-dimethyi-33-diphenyl-2-pyrrolidone Unclear - Unclear Unclear [5], [3]
⏷ 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
Aromatase (CYP19A1) DME0002 Homo sapiens
CP19A_HUMAN
1.14.14.14
[2]
Cytochrome P450 (CYP) DMEN060 . Not Available Not Available [3]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[4]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[5]
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[6]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[5]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[5]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[5]
S-(hydroxymethyl)glutathione dehydrogenase (adh) DME1249 Vibrio cholerae
A0A0A7DS01_VIBCL
1.1.1.284
[3]
⏷ Show the Full List of 13  DME(s)
References
1 Methadone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Bidirectional transfer of methadone across human placenta. Biochem Pharmacol. 2005 Jan 1;69(1):187-97.
3 Effects of cytochrome P450 single nucleotide polymorphisms on methadone metabolism and pharmacodynamics
4 Methadone--metabolism, pharmacokinetics and interactions. Pharmacol Res. 2004 Dec;50(6):551-9.
5 Methadone metabolism and drug-drug interactions: in vitro and in vivo literature review. J Pharm Sci. 2018 Dec;107(12):2983-2991.
6 Involvement of cytochrome P450 3A4 enzyme in the N-demethylation of methadone in human liver microsomes. Chem Res Toxicol. 1996 Mar;9(2):365-73.

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