Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2013-02-08 18:43:49 UTC
HMDB IDHMDB14960
Secondary Accession NumbersNone
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
Thumb
Synonyms
  1. Disulfuram
  2. Disulphuram
  3. Dupon 4472
  4. Dupont Fungicide 4472
  5. TATD
  6. TETD
  7. Tetraethylthioperoxydicarbonic Diamide
  8. Tetraethylthiram Disulfide
  9. Tetraethylthiram Disulphide
  10. Tetraethylthiuram
  11. Tetraethylthiuram Disulfide
  12. Tetraethylthiuram Disulphide
  13. Tetraethylthiuram Sulfide
  14. Tetraethylthiuran Disulfide
  15. TTD
  16. Usaf B-33
Chemical FormulaC10H20N2S4
Average Molecular Weight296.539
Monoisotopic Molecular Weight296.05093141
IUPAC NameN,N-diethyl[(diethylcarbamothioyl)disulfanyl]carbothioamide
Traditional IUPAC NameN,N-diethyl(diethylcarbamothioyl)disulfanylcarbothioamide
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
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassOrganic Disulfides
Sub ClassN/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • a small molecule(Cyc)
  • organic disulfide(ChEBI)
Substituents
  • N/A
Direct ParentOrganic Disulfides
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Alcohol Deterrents
  • Enzyme Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point71.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.26e-02 g/LNot Available
LogP1.9Not Available
Predicted Properties
PropertyValueSource
water solubility0.013 g/LALOGPS
logP3.88ALOGPS
logP4.16ChemAxon
logS-4.4ALOGPS
physiological charge0ChemAxon
hydrogen acceptor count0ChemAxon
hydrogen donor count0ChemAxon
polar surface area6.48ChemAxon
rotatable bond count7ChemAxon
refractivity88.24ChemAxon
polarizability31.6ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Disulfiram PathwaySMP00429Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00822
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00822
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00822
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3005
KEGG Compound IDC01692
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDisulfiram
NuGOwiki LinkHMDB14960
Metagene LinkHMDB14960
METLIN IDNot Available
PubChem Compound3117
PDB IDNot Available
ChEBI ID4659
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. 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

Gene Name:
DBH
Uniprot ID:
P09172
Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP2E1
Uniprot ID:
P05181
Gene Name:
CYP3A5
Uniprot ID:
P20815