Disulfiram

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, 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, dyspnea, 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.

Disulfiram
Clinical data
Trade namesAntabuse, Antabus, other
Other namestetraethyldisulfanedicarbothioamide; 1-(Diethylthiocarbamoyldisulfanyl)-N,N-diethyl-methanethioamide
AHFS/Drugs.comMonograph
MedlinePlusa682602
Pregnancy
category
  • AU: B2
Routes of
administration
By mouth, subdermal implant
ATC code
Legal status
Legal status
  • AU: S6 (Poison) / S4
  • BR: Class C1 (Other controlled substances)
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
Pharmacokinetic data
MetabolismLiver to diethylthiocarbamate
Elimination half-life60–120 hours
Identifiers
  • 1,1′-disulfanediylbis(N,N-diethylmethanethioamide)
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.002.371
Chemical and physical data
FormulaC10H20N2S4
Molar mass296.52 g·mol−1
3D model (JSmol)
SMILES
  • CCN(CC)C(=S)SSC(=S)N(CC)CC
  • InChI=1S/C10H20N2S4/c1-5-11(6-2)9(13)15-16-10(14)12(7-3)8-4/h5-8H2,1-4H3 Y
  • Key:AUZONCFQVSMFAP-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

In the body, alcohol is converted to acetaldehyde, which is then broken down by acetaldehyde dehydrogenase. When the dehydrogenase enzyme is inhibited, acetaldehyde builds up, causing unpleasant side effects (Disulfiram-alcohol reaction). Disulfiram should be used in conjunction with counseling and support.

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