Product Name

Disulfiram

CAS Number

97-77-8

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Product Name:
Disulfiram
CAS Number:
97-77-8
Indication:
For the treatment and management of chronic alcoholism
Mode 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.

Pharmacodynamics:

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.

Metabolism:

Hepatic.

Toxicity:

LD50=8.6g/kg (orally in rats). Symptoms of overdose include irritation, slight drowsiness, unpleasant taste, mild GI disturbances, and orthostatic hypotension.

IUPAC:
N, N-diethyl[(diethylcarbamothioyl)disulfanyl]carbothioamide
ATC:
N07BB01 P03AA04
PubChem:
3117
DrugBank:
DB00822 (APRD00767)
Formula:
C20H28N2O5
Molecular Mass:
296.539
Synonyms:
Disulfuram Disulphuram Dupon 4472 Dupont Fungicide 4472 TATD TETD Tetraethylthioperoxydicarbonic Diamide Tetraethylthiram Disulfide Tetraethylthiram Disulphide Tetraethylthiuram Tetraethylthiuram Disulfide Tetraethylthiuram Disulphide Tetraethylthiuram Sulfide Tetraethylthiuran Disulfide TTD Usaf B-33
SMILES:
CCN(CC)C(=S)SSC(=S)N(CC)CC
InChi:
AUZONCFQVSMFAP-UHFFFAOYSA-N
General Reference:
General Reference:

  1. Nash T, Rice WG: Efficacies of zinc-finger-active drugs against Giardia lamblia. Antimicrob Agents Chemother. 1998 Jun;42(6):1488-92. Pubmed
  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. Pubmed
  3. Gaval-Cruz M, Weinshenker D: mechanisms of disulfiram-induced cocaine abstinence: antabuse and cocaine relapse. Mol Interv. 2009 Aug;9(4):175-87. Pubmed 19720750

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