Drug/Small Molecule:
disulfiram

2D structure

Overview

Generic Names: Disulfuram; Disulphuram; Dupon 4472; Dupont Fungicide 4472; TATD; TETD; TTD; Tetraethylthioperoxydicarbonic Diamide; Tetraethylthiram Disulfide; Tetraethylthiram Disulphide; Tetraethylthiuram; Tetraethylthiuram Disulfide; Tetraethylthiuram Disulphide; Tetraethylthiuram Sulfide; Tetraethylthiuran Disulfide; Usaf B-33
Trade Names: Abstensil; Abstinil; Abstinyl; Accel Tet; Accel Tet-R; Akrochem Tetd; Alcophobin; Alk-Aubs; Ancazide Et; Antabus; Antabuse; Antadix; Antaenyl; Antaethan; Antaethyl; Antaetil; Antalcol; Antetan; Antethyl; Antetil; Anteyl; Anthethyl; Anti-Ethyl; Antiaethan; Anticol; Antietanol; Antietil; Antikol; Antivitium; Aversan; Averzan; Bonibal; Contralin; Contrapot; Cronetal; Dicupral; Disetil; Disulfan; Disulfram; Ekagom Dtet; Ekagom Teds; Ekagom Tetds; Ekaland Tetd; Ephorran; Espenal; Esperal; Etabus; Ethyl Thiram; Ethyl Thiudad; Ethyl Thiurad; Ethyl Tuads; Ethyl Tuads Rodform; Ethyl Tuex; Ethyldithiourame; Ethyldithiurame; Etyl Tuex; Exhoran; Exhorran; Gababentin; Hoca; Krotenal; Nocbin; Nocceler Tet; Nocceler Tet-G; Noxal; Perkacit Tetd; Perkait Tetd; Refusal; Ro-Sulfiram; Sanceler Tet; Sanceler Tet-G; Soxinol Tet; Stopaethyl; Stopethyl; Stopety; Stopetyl; Super Rodiatox; TTS; TTS X; Tenurid; Tenutex; Tetidis; Tetradin; Tetradine; Tetraetil; Teturam; Teturamin; Thiocid; Thiophos; Thioscabin; Thireranide; Tillram; Tiuram
PharmGKB Accession Id: PA449376

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 (source: Drug Bank)

Indication

For the treatment and management of chronic alcoholism (source: Drug Bank)

ATC Therapeutic Categories

  • N07BB:Drugs used in alcohol dependence
  • P03AA:Sulfur containing products

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

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. (source: Drug Bank)

Pharmacology

Disulfiram produces a sensitivity to alcohol which results in a highly unpleasant reaction when the patient under treatment ingests even small amounts of alcohol. Disulfiram blocks the oxidation of alcohol at the acetaldehyde stage during alcohol metabolism following disulfiram intake, the concentration of acetaldehyde occurring in the blood may be 5 to 10 times higher than that found during metabolism of the same amount of alcohol alone. Accumulation of acetaldehyde in the blood produces a complex of highly unpleasant symptoms referred to hereinafter as the disulfiram-alcohol reaction. This reaction, which is proportional to the dosage of both disulfiram and alcohol, will persist as long as alcohol is being metabolized. Disulfiram does not appear to influence the rate of alcohol elimination from the body. Prolonged administration of disulfiram does not produce tolerance; the longer a patient remains on therapy, the more exquisitely sensitive he becomes to alcohol. (source: Drug Bank)

Food Interactions

Avoid alcohol for up to 14 days after treatment has been stopped.
Take without regard to meals. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic. (source: Drug Bank)

Absorption

Disulfiram is absorbed slowly from the gastrointestinal tract (80 to 90% of oral dose). (source: Drug Bank)

Toxicity

LD<sub>50</sub>=8.6g/kg (orally in rats). Symptoms of overdose include irritation, slight drowsiness, unpleasant taste, mild GI disturbances, and orthostatic hypotension. (source: Drug Bank)

Isomeric SMILES Code:

CCN(CC)C(=S)SSC(=S)N(CC)CC (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Has annotations
ABCB1
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  • FA
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Publications
No phenotype data No genotype data Literature annotations available Not annotated
DBH
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  • FA
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Publications

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
ALDH2 Uncurated Annotation (source: Drug Bank)
TSPO Uncurated Annotation (source: Drug Bank)

The following drugs are in curated knowledge about this drug.

  Drug Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Not annotated
warfarin
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Publications

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
acenocoumarol Uncurated Annotation Disulfiram increases the anticoagulant effect (source: Drug Bank)
amprenavir Uncurated Annotation Increased risk of side effects (oral solution) (source: Drug Bank)
chlorzoxazone Uncurated Annotation Increases chlorzoxazone levels (source: Drug Bank)
cocaine Uncurated Annotation Increases the cardiac toxicity of cocaine (source: Drug Bank)
dicumarol Uncurated Annotation Increases the anticoagulant effect (source: Drug Bank)
isoniazid Uncurated Annotation Increased risk of CNS adverse efects (source: Drug Bank)
mephenytoin Uncurated Annotation Increases the effect of phenytoin (source: Drug Bank)
metronidazole Uncurated Annotation Possible acute psychosis and confusion (source: Drug Bank)
phenytoin Uncurated Annotation Increases the effect of phenytoin (source: Drug Bank)
theophylline Uncurated Annotation Increases the effect and toxicity of theophylline (source: Drug Bank)
warfarin Uncurated Annotation Increases the anticoagulant effect (source: Drug Bank)

Curated Information

The following diseases are in curated knowledge about this drug.

  Disease Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
Alcoholism
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  • FA
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Publications
No phenotype data No genotype data Literature annotations available Not annotated
Cocaine-Related Disorders
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  • FA
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Publications
No phenotype data No genotype data Literature annotations available Not annotated
Hypotension
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  • FA
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Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00822
ChEBI ID:
4659
KEGG Compound ID:
C01692
KEGG Drug ID:
D00131
PubChem Compound ID:
3117
PubChem Substance ID:
4833

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

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