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

General Information of Drug (ID: DR0519)
Drug Name
Disulfiram
Synonyms
Dicupral; Disulfan; Disulfuram; Ephorran; Esperal; Etabus; Ethyl Thiram; Ethyl Thiurad; Ethyl Tuex; Ethyl tuads; Ethyldithiurame; Exhorran; Krotenal; Refusal; Tetradine; Tetraethylthiuram disulfide; Tetraetil; Teturam; Teturamin; Alcophobin; Antabus; Antabuse; Antadix; Antaenyl; Antaethyl; Antaetil; Antalcol; Antetan; Antetil; Antiaethan; Anticol; Antietanol; Antietil; Antikol; Antivitium; Aversan; Averzan; Contralin; Contrapot; Cronetal; Thiuranide; disulfiram; 97-77-8; Abstensil; Abstinil; Abstinyl; Bis(diethylthiocarbamoyl) disulfide; Hoca; TETD
Indication Alcohol dependence [ICD11: 6C40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 296.5 Topological Polar Surface Area 121
Heavy Atom Count 16 Rotatable Bond Count 7
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
3117
PubChem SID
4833 ; 86944 ; 604564 ; 841760 ; 3134612 ; 7343344 ; 7847199 ; 8151985 ; 10321282 ; 10538921 ; 11111859 ; 11111860 ; 11363904 ; 11366466 ; 11369028 ; 11371250 ; 11374034 ; 11377190 ; 11466125 ; 11467245 ; 11484927 ; 11485729 ; 11488992 ; 11490221 ; 11492043 ; 11494824 ; 11533044 ; 11533307 ; 14720391 ; 14751553 ; 17405720 ; 22390447 ; 22391499 ; 24278722 ; 24888757 ; 26611716 ; 26680072 ; 26719650 ; 26747681 ; 26747682 ; 26753660 ; 26753661 ; 29222259 ; 46386898 ; 46487911 ; 46506008 ; 47216881 ; 47736606 ; 47810875 ; 48110561
ChEBI ID
ChEBI:4659
CAS Number
97-77-8
TTD Drug ID
D0X5SD
Formula
C10H20N2S4
Canonical SMILES
CCN(CC)C(=S)SSC(=S)N(CC)CC
InChI
1S/C10H20N2S4/c1-5-11(6-2)9(13)15-16-10(14)12(7-3)8-4/h5-8H2,1-4H3
InChIKey
AUZONCFQVSMFAP-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
CS2 DM000120
6348
Unclear 1 [5]
Diethylamine DM000119
8021
Unclear 1 [6]
Diethyldithiocarbamate DM000116
28343
Unclear 1 [5]
Diethyldithiocarbamate s-glucuronide DM000117 N. A. Unclear 1 [6]
Diethyldlthiocarbamic acid DM000113 N. A. Unclear 1 [5]
Disulfiram metabolite inorganic sulfate DM000118 N. A. Unclear 1 [6]
Diethyldithiocarbamic acid methyl ester DM000114
12704
Unclear 2 [5]
Diethylthiocarbamic acid methyl ester DM000115
10240953
Oxidation - Oxidative Desulphurylation 3 [5]
Unclear DM009999 N. A. Oxidation - Thiono-Oxidation 3 [4]
Unclear DM009999 N. A. Oxidation - Sulfoxidation 3 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000884 Disulfiram Diethyldlthiocarbamic acid Unclear Unclear [5]
MR000885 Disulfiram Diethyldithiocarbamate Unclear Unclear [5]
MR000886 Disulfiram Diethyldithiocarbamate s-glucuronide Unclear Unclear [6]
MR000887 Disulfiram Disulfiram metabolite inorganic sulfate Unclear Unclear [6]
MR000888 Disulfiram Diethylamine Unclear Unclear [6]
MR000889 Disulfiram Carbon disulfide Unclear Unclear [5]
MR000881 Diethyldlthiocarbamic acid Diethyldithiocarbamic acid methyl ester Unclear Unclear [5]
MR000882 Diethyldithiocarbamic acid methyl ester Diethylthiocarbamic acid methyl ester Oxidation - Oxidative Desulphurylation Unclear [5]
MR000883 Diethyldithiocarbamic acid methyl ester . Oxidation - Sulfoxidation CYP3A4 ... [4]
⏷ 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 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
References
1 Disulfiram was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Identification of the human P-450 enzymes responsible for the sulfoxidation and thiono-oxidation of diethyldithiocarbamate methyl ester: role of P-450 enzymes in disulfiram bioactivation Alcohol Clin Exp Res. 1998 Sep;22(6):1212-9.
3 Interaction of disulfiram with antiretroviral medications: efavirenz increases while atazanavir decreases disulfiram effect on enzymes of alcohol metabolism. Am J Addict. 2014 Mar-Apr;23(2):137-44.
4 Identification of the human P-450 enzymes responsible for the sulfoxidation and thiono-oxidation of diethyldithiocarbamate methyl ester: role of P-450 enzymes in disulfiram bioactivation. Alcohol Clin Exp Res. 1998 Sep;22(6):1212-9.
5 Pharmacological effects of diethylthiocarbamic acid methyl ester, the active metabolite of disulfiram? Eur J Pharmacol. 1989 Aug 3;166(3):419-25. doi: 10.1016/0014-2999(89)90354-3.
6 IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva:World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work).

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