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QuickView for Disulfiram (compound)

Summary
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PubChem

PubChem Compound 3117

PubChem Compound 3117

Name:	Disulfiram
PubChem Compound ID:	3117
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.
Molecular formula:	C₁₀H₂₀N₂S₄
Molecular weight:	296.543 g/mol
Synonyms:	Anticol; Tetraethylthiram disulfide; Exhoran; KBioSS_001490; S00294; Antiaethan; Disulfide, bis (diethylthiocarbamoyl); Formamide, 1, 1'-dithiobis(N,N-diethylthio)-; EU-0101164; Ethyldithiurame. show more » Anticol; Tetraethylthiram disulfide; Exhoran; KBioSS_001490; S00294; Antiaethan; Disulfide, bis (diethylthiocarbamoyl); Formamide, 1, 1'-dithiobis(N,N-diethylthio)-; EU-0101164; Ethyldithiurame; Spectrum2_001176; Thioperoxydicarbonic diamide, tetraethyl-; Disulfiram; Thiosan; Disulfirame [DCIT]; Bis(diethylthiocarbamoyl)disulphide; Antaetil; Bonibal; CHEBI:4659; Tenutex; Bis(N,N-diethylthiocarbamoyl)disulphide; Tetraetil; Nocceler TET-G; Antabuse (TN); Contralin; 1,1',1'',1'''-[disulfanediylbis(carbonothioylnitrilo)]tetraethane; Thiuram disulfide, tetraethyl-; Noxal (VAN); CAS-97-77-8; Stopaethyl; Ethyl Tuex; Tetraethylthiuram disulfide; Anthethyl; Krotenal; Thiocid; Disulfiram [BAN:INN:JAN]; Stopetyl; N,N,N',N'-Tetraethylthiuram disulphide; tetraethylthiuram disulphide; Anteyl; KBio2_001490; Disulfiramo [INN-Spanish]; ENT 27,340; Nocbin; Ethyl Thiram; N,N,N',N'-tetraethylthiuram disulfide; Abstinil; Aversan; Ephorran; SPBio_001191; Ekagom TEDS; InChI=1/C10H20N2S4/c1-5-11(6-2)9(13)15-16-10(14)12(7-3)8-4/h5-8H2,1-4H; D00131; Tuads, ethyl; AI3-27340; SPBio_001993; Espenal; Thireranide; KBio2_004058; bis(diethylthiocarbamoyl) disulfide; Disetil; Noxal; Esperal; anti-Ethyl; SMR000059171; Thioperoxydicarbonic diamide ([(H2N)C(S)]2S2), tetraethyl-; Antadix; Thioscabin; NSC 25953; Antaenyl; Usaf B-33; Thiuranide; Prestwick_182; Tetraethylthiram disulphide; 97-77-8; Contrapot; tetraethylthioperoxydicarbonic diamide; Disulfan; Tetidis; Teturam; Accel TET; Ro-Sulfiram; Spectrum4_000228; Ro-Sulfram-500 (USA); Antikol; NSC25953; Abstinyl; Stopethyl; Thiuram E; Antabus; Etabus; TETD; Ethyl Thiudad; Tetraethylthiuram sulfide; 1,1'-Dithiobis[N,N-diethylthioformamide]; Teturamin; Dupont fungicide 4472; Antaethyl; Dupon 4472; Formamide, 1,1'-dithiobis(N,N-diethylthio-; Bis(N,N-diethylthiocarbamoyl) disulfide; Antietanol; Antietil; Disulfuram; Antivitium (Spain); Antalcol; Disulfiram (JP15/USP); HSDB 3317; Refusal [Netherlands]; Alcophobin; Stopety; CCRIS 582; Prestwick0_000097; Ekagom TETDS; Tetraethylthiurium disulfide; AIDS-010293; Bis[(diethylamino)thioxomethyl] disulfide; Bis(N, N-diethylthiocarbamoyl) disulfide; Spectrum_001010; Alk-Aubs; KBio2_006626; Averzan; Sanceler TET-G; NSC 190940; Abstensyl (Argentina); UPCMLD-DP090:001; Nocceler TET; 11078-22-1; KBio3_001150; NCI-C02959; TATD; Lopac-T-1132; Ekagom DTET; Tetradine; AIDS010293; TTD; Ethyl tuads; Tetraethylthiuram; Tetradin; Tiuram; Disulfide, bis(diethylthiocarbamoyl); Antabuse; Refusal; DRG-0068; TTS; Bis(diethylthiocarbamyl) disulfide; Antethyl; Cronetal; Hocakrotenalnci-C02959; Ethyldithiourame; Tetraethylthiuran disulfide; Dicupral; Esperal [France]; KBioGR_000895; C01692; Tenurid; Abstensil; Antetan; Antivitium; Exhorran; Prestwick1_000097; 155-01-1; Antetil; NCGC00016000-01; Hoca; Soxinol TET; NCGC00016000-02; Spectrum3_000405; MLS000069818; Bis((diethylamino)thioxomethyl) disulfide; Thioperoxydicarbonic diamide (((H2N)C(S))2S2), tetraethyl-; Accel TET-R; Antaethan; Disulfiramum [INN-Latin]; Ethyl Thiurad; Tillram; Sanceler TET; EINECS 202-607-8; Bis((diethylamino)thioxomethyl)disulphide; 1,1'-dithiobis(N,N-diethylthioformamide) show less «

DrugBank

Identification

Name:	Disulfiram
Name (isomeric):	DB00822
Drug Type:	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.
Synonyms:	Tetraethylthiuram Disulphide; Dupont Fungicide 4472; Usaf B-33; Tetraethylthioperoxydicarbonic Diamide; TTD; Tetraethylthiuran Disulfide; TETD; Tetraethylthiuram; Tetraethylthiuram Disulfide; Tetraethylthiram Disulfide. show more » Tetraethylthiuram Disulphide; Dupont Fungicide 4472; Usaf B-33; Tetraethylthioperoxydicarbonic Diamide; TTD; Tetraethylthiuran Disulfide; TETD; Tetraethylthiuram; Tetraethylthiuram Disulfide; Tetraethylthiram Disulfide; Dupon 4472; Disulphuram; Tetraethylthiram Disulphide; Disulfuram; TATD; Tetraethylthiuram Sulfide show less «
Brand:	Thiocid, Teturamin, Antaenyl, Ephorran, Antabus, Antadix, Anteyl, Tetradine, Accel Tet-R, Stopaethyl, Antivitium, Antaethyl, TTS, Etabus, Antaetil, Contrapot, Ethyl Tuads Rodform, Super Rodiatox, Antetan, Soxinol Tet, Stopety, Ekagom Tetds, Antabuse, Antethyl, Antietanol, Disulfram, Esperal, Tenurid, Sanceler Tet-G, Tetidis, Abstinyl, Averzan, Tiuram, Antiaethan, Ekaland Tetd, Tetradin, Ethyldithiourame, Ethyl Thiram, Contralin, Alk-Aubs, Refusal, Espenal, Tillram, Aversan, Teturam, Disulfan, Ethyldithiurame, Stopetyl, Antaethan, Ekagom Dtet, Cronetal, Tetraetil, Abstinil, Thireranide, Nocceler Tet-G, Krotenal, Antalcol, Perkacit Tetd, Ancazide Et, Accel Tet, Thioscabin, Alcophobin, Bonibal, Disetil, Exhorran, Abstensil, Ekagom Teds, Ethyl Thiurad, Perkait Tetd, Exhoran, Antietil, Tenutex, Anticol, Ro-Sulfiram, Akrochem Tetd, Nocbin, Ethyl Tuads, Stopethyl, Nocceler Tet, Gababentin, Antetil, Noxal, Thiophos, Hoca, Ethyl Tuex, Anthethyl, TTS X, Ethyl Thiudad, Anti-Ethyl, Antikol, Sanceler Tet, Etyl Tuex, Dicupral
Category:	Enzyme Inhibitors, Alcohol Deterrents
CAS number:	97-77-8

Pharmacology

Indication:	For the treatment and management of chronic alcoholism
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... show more » 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. show less «
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 ste... show more » 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. show less «
Absorption:	Disulfiram is absorbed slowly from the gastrointestinal tract (80 to 90% of oral dose).
Biotransformation:	Hepatic.
Toxicity:	LD₅₀=8.6g/kg (orally in rats). Symptoms of overdose include irritation, slight drowsiness, unpleasant taste, mild GI disturbances, and orthostatic hypotension.
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Avoid alcohol for up to 14 days after treatment has been stopped.

Take without regard to meals.

Drug interaction:

Warfarin	Disulfiram may increase the anticoagulant effect of warfarin.
Trimethadione	Disulfiram, a strong CYP2E1 inhibitor, may decrease the metabolism and clearance of Trimethadione, a CYP2E1 substrate. Consider alternate therapy or monitor for changes in Trimethadione therapeutic and adverse effects if Disulfiram is initiated, discontinued or dose changed.
Phenytoin	Disulfiram may increase the therapeutic and adverse effects of phenytoin.
Anisindione	Disulfiram may increase the anticoagulant effect of anisindione.
Aminophylline	Disulfiram may increase the effect and toxicity of aminophylline.

Targets

Aldehyde dehydrogenase, mitochondrial

Dopamine beta-hydroxylase

Enzymes

Cytochrome P450 2E1

Cytochrome P450 2C9

Cytochrome P450 3A4

Cytochrome P450 3A5