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Details

Stereochemistry ACHIRAL
Molecular Formula C10H20N2S4
Molecular Weight 296.539
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DISULFIRAM

SMILES

CCN(CC)C(=S)SSC(=S)N(CC)CC

InChI

InChIKey=AUZONCFQVSMFAP-UHFFFAOYSA-N
InChI=1S/C10H20N2S4/c1-5-11(6-2)9(13)15-16-10(14)12(7-3)8-4/h5-8H2,1-4H3

HIDE SMILES / InChI

Description

Disulfiram is 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. 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. Used for the treatment and management of chronic alcoholism.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.3 µM [IC50]
101.0 µM [IC50]
4.6 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Disulfiram

Cmax

ValueDoseCo-administeredAnalytePopulation
1.3 nM
500 mg single, oral
DISULFIRAM plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.3 h
500 mg single, oral
DISULFIRAM plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Alcohol Dependence -Initial dose: 500 mg orally once a day (this dose is generally continued for the first 1 to 2 weeks) -Maintenance dose: 250 mg orally once a day (range: 125 mg to 500 mg once a day) Maximum dose: 500 mg once a day -Duration of therapy: Depending on the individual, therapy may last months or even years
Route of Administration: Oral
In Vitro Use Guide
Application of 1mM disulfiram to R. jostii RHA1, gave rise to 4-carboxymuconolactone on the β-ketoadipate pathway