ContaminantDB: Disulfiram

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (25)XML

Record Information

Version

1.0

Creation Date

2009-07-05 02:56:35 UTC

Update Date

2026-05-14 16:49:54 UTC

Accession Number

CHEM002084

Identification

Common Name

Disulfiram

Class

Small Molecule

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]

Contaminant Sources

HMDB Contaminants - Urine
HPV EPA Chemicals
IARC Carcinogens Group 3
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Alcohol Deterrent
Amine
Drug
Enzyme Inhibitor
Human Neurotoxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,1'-Dithiobis(N,N-diethylthioformamide)	ChEBI
Antabuse	ChEBI
Bis(diethylthiocarbamoyl) disulfide	ChEBI
N,N,N',n'-tetraethylthiuram disulfide	ChEBI
Tetraethylthioperoxydicarbonic diamide	ChEBI
Tetraethylthiuram disulfide	ChEBI
Tetraethylthiuram disulphide	ChEBI
Bis(diethylthiocarbamoyl) disulphide	Generator
N,N,N',n'-tetraethylthiuram disulphide	Generator
Disulphiram	Generator
Disulfuram	HMDB
Disulphuram	HMDB
Dupon 4472	HMDB
Dupont fungicide 4472	HMDB
TATD	HMDB
TETD	HMDB
Tetraethylthiram disulfide	HMDB
Tetraethylthiram disulphide	HMDB
Tetraethylthiuram	HMDB
Tetraethylthiuram sulfide	HMDB
Tetraethylthiuran disulfide	HMDB
TTD	HMDB
Usaf b-33	HMDB
Allphar brand OF disulfiram	HMDB
Altana pharma brand OF disulfiram	HMDB
Antabus	HMDB
Anticol	HMDB
Disulfide, tetraethylthiuram	HMDB
Tetraethylthioperoxydicarbonic diamide, ((H2N)C(S))2S2	HMDB
Alcophobin	HMDB
Esperal	HMDB
Sanofi synthelabo brand OF disulfiram	HMDB
Bohm brand OF disulfiram	HMDB
Odyssey brand OF disulfiram	HMDB
Orphan brand OF disulfiram	HMDB
Dicupral	HMDB
Dumex brand OF disulfiram	HMDB
Teturam	HMDB

Chemical Formula

C₁₀H₂₀N₂S₄

Average Molecular Mass

296.539 g/mol

Monoisotopic Mass

296.051 g/mol

CAS Registry Number

97-77-8

IUPAC Name

N,N-diethyl[(diethylcarbamothioyl)disulfanyl]carbothioamide

Traditional Name

disulfiram

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

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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Thiuram disulfides

Alternative Parents

Substituents

Thiuram disulfide
Organic disulfide
Sulfenyl compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tertiary amino compound (CHEBI:4659 )
organic disulfide (CHEBI:4659 )
a small molecule (DISULFIRAM )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Disulfiram Pathway	Not Available	Not Available

Applications

Not Available

Biological Roles

EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor

Chemical Roles

EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	71.5°C
Boiling Point	117°C at 1.70E+01 mm Hg
Solubility	4.09 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	3.88	ALOGPS
logP	4.16	ChemAxon
logS	-4.4	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	88.24 m³·mol⁻¹	ChemAxon
Polarizability	31.6 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-016r-8930000000-ff4b800eacdb52d66d80	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-014i-0900000000-274003127d4c34f9abcc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-002b-1910000000-0371815b89a4378bec81	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-0950000000-ca28d8dfdf780c201716	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-0950000000-ca28d8dfdf780c201716	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0a4i-5910000000-7dd7b7fbb29b6ae08f4c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00xr-0904000000-2d29367629d096da4708	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00xr-1914000000-0022574151f222c8050f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014j-0900000000-07fd862cac7fb47fa007	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-0903000000-bb7b2b338b8981b249ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00kb-3910100000-263484085094fbdd45da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014s-5900000000-fe9f3fb3c9d4c94f6496	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-1970000000-87dad5bd832c248e4c73	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-3900000000-f7637bebace8002bdd78	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9500000000-491cc5b9b0d4455ff674	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01vk-4690000000-64528d1f9696aa7a5d5d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02ft-9810000000-825b92854771a0e58c9d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fdo-8910000000-afd3a638d74e8761c518	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0910000000-cf16eb2676d288479eac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2900000000-2765ff0428d56cf81049	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9200000000-7f8c0eb726cf3929fa7f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-3690000000-f14241348cdf9f8196d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ot-7900000000-1843982004d8ffd33a5f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9200000000-28f4b4954161ce60f733	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-014r-9510000000-2e18f478f9c0f9a2958a	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (MSDS, A308); ingestion (MSDS, A308); dermal (MSDS, A308) ; eye contact (MSDS, A308) Disulfiram is absorbed slowly from the gastrointestinal tract (80 to 90% of oral dose).

Mechanism of Toxicity

Disulfiram blocks the oxidation of alcohol at the acetaldehyde stage during alcohol metabolism following disulfiram intake causing an accumulation of acetaldehyde in the blood producing highly unpleasant symptoms. Disulfiram blocks the oxidation of alcohol through its irreversible inactivation of aldehyde dehydrogenase, which acts in the second step of ethanol utilization. In addition, disulfiram competitively binds and inhibits the peripheral benzodiazepine receptor, which may indicate some value in the treatment of the symptoms of alcohol withdrawal, however this activity has not been extensively studied.

Metabolism

Disulfiram is completely absorbed from the human GI tract. However, a period of 12 hr is required for its full action, perhaps because, being highly sol in lipid, it is initially localized in fat. It is slowly metabolized in the liver to diethyldithiocarbamate, diethylamine, and carbon disulfide. Six hr after oral administration of the drug, one third of plasma disulfiram is in the form of diethyldithiocarbamate. Elimination is relatively slow, and about 1/5 still remains in body at end of a week. The greater part of the absorbed drug is excreted in the urine as the sulfate, partly free and partly esterified (2, 3).

Toxicity Values

LD50: 8.6g/kg (oral, rat).

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (7)

Uses/Sources

For the treatment and management of chronic alcoholism (1).

Minimum Risk Level

Not Available

Health Effects

Occasionally implicated in producing psychosis, optic neuritis, and encephalopathy. Hematologic, neuromuscular, and gastrointestinal toxicity and hepatotoxicity may occur 10 days to 12 months after therapy is begun (10).

Symptoms

Symptoms of overdose include irritation, slight drowsiness, unpleasant taste, mild GI disturbances, and orthostatic hypotension.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00822

HMDB ID

HMDB0014960

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Adams, H.S. and Meuser, L.; US.Patent 1,782,111; November 18,1930; assigned to The
Naugatuck Chemical Company.
Bailey, G.C.; U.S.Patent 1,796,977; March 17,1931; assigned to The Roessler & Hasslacher
Chemical Company.

MSDS

Link

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.

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.

3. 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.

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=10841824

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11005259

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=11716515

7. https://www.ncbi.nlm.nih.gov/pubmed/?term=14978246

8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15325261

9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15709459