Disulfiram

Disulfiram
Clinical data
Trade names	Antabuse, Antabus, other
Other names	tetraethyldisulfanedicarbothioamide; 1-(Diethylthiocarbamoyldisulfanyl)-N,N-diethyl-methanethioamide
AHFS/Drugs.com	Monograph
MedlinePlus	a682602
Pregnancy; category	AU: B2;
Routes of; administration	By mouth, subdermal implant
ATC code	N07BB01 (WHO) P03AA04 (WHO);
Legal status
Legal status	AU: S6 (Poison) / S4; BR: Class C1 (Other controlled substances); UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Metabolism	Liver to diethylthiocarbamate
Elimination half-life	60–120 hours
Identifiers
	IUPAC name 1,1′-disulfanediylbis(N,N-diethylmethanethioamide);
CAS Number	97-77-8 ;
PubChem CID	3117;
IUPHAR/BPS	7168;
DrugBank	DB00822 ;
ChemSpider	3005 ;
UNII	TR3MLJ1UAI;
KEGG	D00131 ;
ChEBI	CHEBI:4659 ;
ChEMBL	ChEMBL964 ;
NIAID ChemDB	010293;
CompTox Dashboard (EPA)	DTXSID1021322 ;
ECHA InfoCard	100.002.371
Chemical and physical data
Formula	C10H20N2S4
Molar mass	296.52 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)C(=S)SSC(=S)N(CC)CC;
	InChI InChI=1S/C10H20N2S4/c1-5-11(6-2)9(13)15-16-10(14)12(7-3)8-4/h5-8H2,1-4H3 ; Key:AUZONCFQVSMFAP-UHFFFAOYSA-N ;
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Disulfiram is a medication used to support the treatment of chronic alcoholism by producing an acute sensitivity to ethanol (drinking alcohol). Disulfiram works by inhibiting the enzyme aldehyde dehydrogenase (specifically ALDH2), causing many of the effects of a hangover to be felt immediately following alcohol consumption. Disulfiram plus alcohol, even small amounts, produces flushing, throbbing in the head and neck, a throbbing headache, respiratory difficulty, nausea, copious vomiting, sweating, thirst, chest pain, palpitation, shortness of breath, hyperventilation, fast heart rate, low blood pressure, fainting, marked uneasiness, weakness, vertigo, blurred vision, and confusion. In severe reactions there may be respiratory depression, cardiovascular collapse, abnormal heart rhythms, heart attack, acute congestive heart failure, unconsciousness, convulsions, and death.

In the body, alcohol is converted to acetaldehyde, which is then broken down by ALDH2. When the dehydrogenase enzyme is inhibited, acetaldehyde builds up, causing unpleasant side effects. The clinical use of disulfiram mimics the genetic predisposition to alcohol intolerance found in East Asian populations due to the mutation of the ALDH2 gene.