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

General Information of Drug (ID: DR2515)
Drug Name
Methimazole
Synonyms
Mercaptazole; Mercasolyl; Mercazole; Mercazolyl; Mercazolylum; Merkastan; Merkazolil; Metazolo; Methiamazole; Methimazol; Methimazolum; Methylmercaptoimidazole; Metizol; Metothyrin; Metothyrine; Metotirin; Strumazol; Tapazole; Thacapzol; Basolan; Danantizol; Favistan; Frentirox; Thiamazol; Thycapsol; Thycapzol; Thymidazol; Thymidazole; Tiamazol; Usaf el-30; methimazole; thiamazole; 1-Methyl-1H-imidazole-2-thiol; 1-Methyl-2-mercaptoimidazole; 1-Methylimidazole-2-thiol; 2-Mercapto-1-methylimidazole; 3-methyl-1H-imidazole-2-thione; 60-56-0
Indication Thyrotoxicosis [ICD11: 5A02] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 114.17 Topological Polar Surface Area 47.4
Heavy Atom Count 7 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
1349907
ChEBI ID
CHEBI:50673
CAS Number
60-56-0
Formula
C4H6N2S
Canonical SMILES
CN1C=CNC1=S
InChI
1S/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)
InChIKey
PMRYVIKBURPHAH-UHFFFAOYSA-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
Methimazole Metabolite 6 DM016104
45087423
Unclear - Unclear 1 [2]
Methimazole M13 DM016545
119092457
Unclear - Unclear 1 [2]
Methimazole N-methyl Thiourea DM015363
2723704
Unclear - Unclear 1 [2] , [3]
Methimazole M14 DM016106
45088108
Unclear - Unclear 2 [2]
Methimazole M7 DM015370
2763436
Unclear - Unclear 2 [2]
Methimazole M8 DM014822
650
Unclear - Unclear 3 [2]
Methimazole N-methyl Thiourea DM015363
2723704
Unclear - Unclear 3 [2]
Methimazole M9 DM017959 N. A. Unclear - Unclear 4 [2]
Methimazole M10 DM016000
22034929
Unclear - Unclear 5 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013809 Methimazole Methimazole M6 Unclear - Unclear CYP [2]
MR013815 Methimazole Methimazole M13 Unclear - Unclear Unclear [2]
MR013817 Methimazole N-methylthiourea Unclear - Unclear CYP2A6 [2], [3]
MR013816 Methimazole M13 Methimazole M14 Unclear - Unclear Unclear [2]
MR013810 Methimazole M6 Methimazole M7 Unclear - Unclear Unclear [2]
MR013811 Methimazole M7 Methimazole M5b Unclear - Unclear Unclear [2]
MR013814 Methimazole M7 Methimazole M8 Unclear - Unclear Unclear [2]
MR013812 Methimazole M5b Methimazole M9 Unclear - Unclear Unclear [2]
MR013813 Methimazole M9 Methimazole M10 Unclear - Unclear FMO [2]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2] , [3]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[3]
Dimethylaniline oxidase 2 (FMO2) DME0283 Homo sapiens
FMO2_HUMAN
1.14.13.8
[4]
References
1 Methimazole was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Evidence for the involvement of N-methylthiourea, a ring cleavage metabolite, in the hepatotoxicity of methimazole in glutathione-depleted mice: structure-toxicity and metabolic studies
3 Role of CYP2A6 in Methimazole Bioactivation and Hepatotoxicity
4 Drug metabolism by flavin-containing monooxygenases of human and mouse. Expert Opin Drug Metab Toxicol. 2017 Feb;13(2):167-181.

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