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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:48 UTC
HMDB IDHMDB0014960
Secondary Accession Numbers
  • HMDB14960
Metabolite Identification
Common NameDisulfiram
DescriptionA carbamate derivative used as an alcohol deterrent. It is a relatively nontoxic substance when administered alone, but markedly alters the intermediary metabolism of alcohol. When alcohol is ingested after administration of disulfiram, blood acetaldehyde concentrations are increased, followed by flushing, systemic vasodilation, respiratory difficulties, nausea, hypotension, and other symptoms (acetaldehyde syndrome). It acts by inhibiting aldehyde dehydrogenase. [PubChem]
Structure
Data?1582753242
Synonyms
ValueSource
1,1'-Dithiobis(N,N-diethylthioformamide)ChEBI
AntabuseChEBI
Bis(diethylthiocarbamoyl) disulfideChEBI
N,N,N',n'-tetraethylthiuram disulfideChEBI
Tetraethylthioperoxydicarbonic diamideChEBI
Tetraethylthiuram disulfideChEBI
Tetraethylthiuram disulphideChEBI
Bis(diethylthiocarbamoyl) disulphideGenerator
N,N,N',n'-tetraethylthiuram disulphideGenerator
DisulphiramGenerator
DisulfuramHMDB
DisulphuramHMDB
Dupon 4472HMDB
Dupont fungicide 4472HMDB
TATDHMDB
TETDHMDB
Tetraethylthiram disulfideHMDB
Tetraethylthiram disulphideHMDB
TetraethylthiuramHMDB
Tetraethylthiuram sulfideHMDB
Tetraethylthiuran disulfideHMDB
TTDHMDB
Usaf b-33HMDB
Allphar brand OF disulfiramHMDB
Altana pharma brand OF disulfiramHMDB
AntabusHMDB
AnticolHMDB
Disulfide, tetraethylthiuramHMDB
Tetraethylthioperoxydicarbonic diamide, ((H2N)C(S))2S2HMDB
AlcophobinHMDB
EsperalHMDB
Sanofi synthelabo brand OF disulfiramHMDB
Bohm brand OF disulfiramHMDB
Odyssey brand OF disulfiramHMDB
Orphan brand OF disulfiramHMDB
DicupralHMDB
Dumex brand OF disulfiramHMDB
TeturamHMDB
Chemical FormulaC10H20N2S4
Average Molecular Weight296.539
Monoisotopic Molecular Weight296.05093141
IUPAC NameN,N-diethyl[(diethylcarbamothioyl)disulfanyl]carbothioamide
Traditional Namedisulfiram
CAS Registry Number97-77-8
SMILES
CCN(CC)C(=S)SSC(=S)N(CC)CC
InChI Identifier
InChI=1S/C10H20N2S4/c1-5-11(6-2)9(13)15-16-10(14)12(7-3)8-4/h5-8H2,1-4H3
InChI KeyAUZONCFQVSMFAP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiuram disulfides. These are organic disulfides that have the general structural formula RN(R')C(=S)SSC(=S)N(R\")R\"', where R-R\"'=alkyl groups.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentThiuram disulfides
Alternative Parents
Substituents
  • Thiuram disulfide
  • Organic disulfide
  • Sulfenyl compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point71.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.013 g/LNot Available
LogP1.9Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available165.48http://allccs.zhulab.cn/database/detail?ID=AllCCS00000708
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP3.88ALOGPS
logP4.16ChemAxon
logS-4.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity88.24 m³·mol⁻¹ChemAxon
Polarizability31.6 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.92831661259
DarkChem[M-H]-165.97231661259
DeepCCS[M+H]+159.91530932474
DeepCCS[M-H]-157.55730932474
DeepCCS[M-2H]-191.57830932474
DeepCCS[M+Na]+166.51330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DisulfiramCCN(CC)C(=S)SSC(=S)N(CC)CC3506.8Standard polar33892256
DisulfiramCCN(CC)C(=S)SSC(=S)N(CC)CC2101.6Standard non polar33892256
DisulfiramCCN(CC)C(=S)SSC(=S)N(CC)CC2526.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Disulfiram GC-MS (Non-derivatized) - 70eV, Positivesplash10-016r-8930000000-ff4b800eacdb52d66d802017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Disulfiram GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-014r-9510000000-2e18f478f9c0f9a2958a2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Disulfiram LC-ESI-qTof , Positive-QTOFsplash10-014i-0900000000-274003127d4c34f9abcc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Disulfiram LC-ESI-qTof , Positive-QTOFsplash10-002b-1910000000-0371815b89a4378bec812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Disulfiram LC-ESI-qTof , Positive-QTOFsplash10-004i-0950000000-ca28d8dfdf780c2017162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Disulfiram LC-ESI-qTof , Positive-QTOFsplash10-004i-0950000000-ca28d8dfdf780c2017162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Disulfiram LC-ESI-qTof , Positive-QTOFsplash10-0a4i-5910000000-7dd7b7fbb29b6ae08f4c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Disulfiram , positive-QTOFsplash10-00xr-0904000000-2d29367629d096da47082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Disulfiram , positive-QTOFsplash10-00xr-1914000000-0022574151f222c8050f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Disulfiram , positive-QTOFsplash10-014j-0900000000-07fd862cac7fb47fa0072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Disulfiram , positive-QTOFsplash10-00di-0903000000-bb7b2b338b8981b249ac2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Disulfiram , positive-QTOFsplash10-00kb-3910100000-263484085094fbdd45da2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Disulfiram 35V, Positive-QTOFsplash10-014s-5900000000-fe9f3fb3c9d4c94f64962021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disulfiram 10V, Positive-QTOFsplash10-0002-1970000000-87dad5bd832c248e4c732016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disulfiram 20V, Positive-QTOFsplash10-014i-3900000000-f7637bebace8002bdd782016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disulfiram 40V, Positive-QTOFsplash10-00di-9500000000-491cc5b9b0d4455ff6742016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disulfiram 10V, Negative-QTOFsplash10-01vk-4690000000-64528d1f9696aa7a5d5d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disulfiram 20V, Negative-QTOFsplash10-02ft-9810000000-825b92854771a0e58c9d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disulfiram 40V, Negative-QTOFsplash10-0fdo-8910000000-afd3a638d74e8761c5182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disulfiram 10V, Positive-QTOFsplash10-014i-0910000000-cf16eb2676d288479eac2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disulfiram 20V, Positive-QTOFsplash10-014i-2900000000-2765ff0428d56cf810492021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disulfiram 40V, Positive-QTOFsplash10-000i-9200000000-7f8c0eb726cf3929fa7f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disulfiram 10V, Negative-QTOFsplash10-0002-3690000000-f14241348cdf9f8196d22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disulfiram 20V, Negative-QTOFsplash10-01ot-7900000000-1843982004d8ffd33a5f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Disulfiram 40V, Negative-QTOFsplash10-03di-9200000000-28f4b4954161ce60f7332021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00822 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00822 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00822
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3005
KEGG Compound IDC01692
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDisulfiram
METLIN IDNot Available
PubChem Compound3117
PDB IDNot Available
ChEBI ID4659
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gaval-Cruz M, Weinshenker D: mechanisms of disulfiram-induced cocaine abstinence: antabuse and cocaine relapse. Mol Interv. 2009 Aug;9(4):175-87. doi: 10.1124/mi.9.4.6. [PubMed:19720750 ]
  2. Nash T, Rice WG: Efficacies of zinc-finger-active drugs against Giardia lamblia. Antimicrob Agents Chemother. 1998 Jun;42(6):1488-92. [PubMed:9624499 ]
  3. Bouma MJ, Snowdon D, Fairlamb AH, Ackers JP: Activity of disulfiram (bis(diethylthiocarbamoyl)disulphide) and ditiocarb (diethyldithiocarbamate) against metronidazole-sensitive and -resistant Trichomonas vaginalis and Tritrichomonas foetus. J Antimicrob Chemother. 1998 Dec;42(6):817-20. [PubMed:10052908 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Conversion of dopamine to noradrenaline.
Gene Name:
DBH
Uniprot ID:
P09172
Molecular weight:
69064.45
References
  1. Gaval-Cruz M, Weinshenker D: mechanisms of disulfiram-induced cocaine abstinence: antabuse and cocaine relapse. Mol Interv. 2009 Aug;9(4):175-87. doi: 10.1124/mi.9.4.6. [PubMed:19720750 ]
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
References
  1. Mackenzie IS, Maki-Petaja KM, McEniery CM, Bao YP, Wallace SM, Cheriyan J, Monteith S, Brown MJ, Wilkinson IB: Aldehyde dehydrogenase 2 plays a role in the bioactivation of nitroglycerin in humans. Arterioscler Thromb Vasc Biol. 2005 Sep;25(9):1891-5. Epub 2005 Jul 28. [PubMed:16051882 ]
  2. Ho MP, Yo CH, Liu CM, Chen CL, Lee CC: Refractive hypotension in a patient with disulfiram-ethanol reaction. Am J Med Sci. 2007 Jan;333(1):53-5. [PubMed:17220694 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]