Human Metabolome Database Version 3.5

Showing metabocard for Disulfiram (HMDB14960)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:50 -0600
Update Date 2013-02-08 11:43:49 -0700
HMDB ID HMDB14960
Secondary Accession Numbers None
Metabolite Identification
Common Name Disulfiram
Description A 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C10H20N2S4
Average Molecular Weight 296.539
Monoisotopic Molecular Weight 296.05093141
IUPAC Name N,N-diethyl[(diethylcarbamothioyl)disulfanyl]carbothioamide
Traditional IUPAC Name N,N-diethyl(diethylcarbamothioyl)disulfanylcarbothioamide
CAS Registry Number 97-77-8
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 Key AUZONCFQVSMFAP-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Organic Disulfides
Sub Class N/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • a small molecule(Cyc)
  • organic disulfide(ChEBI)
Substituents
  • N/A
Direct Parent Organic Disulfides
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Alcohol Deterrents
  • Enzyme Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 71.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1.26e-02 g/L Not Available
LogP 1.9 Not Available
Predicted Properties
Property Value Source
LogP 3.88 ALOGPS
LogP 4.16 ChemAxon
LogS -4.37 ALOGPS
Hydrogen Acceptor Count 0 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 6.48 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 88.24 ChemAxon
Polarizability 31.6 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Disulfiram Pathway SMP00429 Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00822
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00822
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00822 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 3005 Link_out
KEGG Compound ID C01692 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Disulfiram Link_out
NuGOwiki Link HMDB14960 Link_out
Metagene Link HMDB14960 Link_out
METLIN ID Not Available
PubChem Compound 3117 Link_out
PDB ID Not Available
ChEBI ID 4659 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Nash T, Rice WG: Efficacies of zinc-finger-active drugs against Giardia lamblia. Antimicrob Agents Chemother. 1998 Jun;42(6):1488-92. Pubmed: 9624499 Link_out
  2. 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 Link_out
  3. 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 Link_out

Enzymes
Name: Dopamine beta-hydroxylase
Reactions: Not Available
Gene Name: DBH
Uniprot ID: P09172 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: ALDH2
Uniprot ID: P05091 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2E1
Reactions: Not Available
Gene Name: CYP2E1
Uniprot ID: P05181 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A5
Reactions: Not Available
Gene Name: CYP3A5
Uniprot ID: P20815 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA