DISULFIRAM

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 Search

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

Molecular Formula	C10H20N2S4
Molecular Weight	296.539
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00822
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/disulfiram.html

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 Target	Pharmacology	Potency
Aldehyde dehydrogenase 8 Target ID: CHEMBL1935 Sources: http://www.drugbank.ca/drugs/DB00822	Inhibitor 8504
Arylamine N-acetyltransferase 1 4 Target ID: CHEMBL5101 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19664055	Inhibitor 8504	3.3 µM [IC50]
Aldehyde dehydrogenase 1A1 5 Target ID: CHEMBL3577 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19296407	Inhibitor 8504	101.0 µM [IC50]
leukotriene B4 biosynthetic process 8 Target ID: GO:0097251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1647348	Inhibitor 8504	4.6 µM [IC50]
Dopamine beta-hydroxylase 17 Target ID: CHEMBL3102 Sources: http://www.drugbank.ca/drugs/DB00822	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic alcoholism 1 Sources: https://www.drugs.com/pro/disulfiram.html	Primary		Approved 8583	Disulfiram Approved Use Disulfiram is an aid in the management of selected chronic alcohol patients who want to remain in a state of enforced sobriety so that supportive and psychotherapeutic treatment may be applied to best advantage. Launch Date 1981

C_max

Value	Dose	Co-administered	Analyte	Population
1.3 nM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1471547	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		DISULFIRAM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
54.696 ng/mL EXPERIMENT https://www.accessdata.fda.gov/drugsatfda_docs/anda/2011/091619Orig1s000BioeqR.pdf#page=19	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		DISULFIRAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
715.144 ng × h/mL EXPERIMENT https://www.accessdata.fda.gov/drugsatfda_docs/anda/2011/091619Orig1s000BioeqR.pdf#page=19	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		DISULFIRAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.3 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1471547	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		DISULFIRAM plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
9.82 h EXPERIMENT https://www.accessdata.fda.gov/drugsatfda_docs/anda/2011/091619Orig1s000BioeqR.pdf#page=19	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		DISULFIRAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2E1 1060 CYP2C19 2057

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10348802/	no		no (co-administration study) Comment: Results show that single-dose disulfiram does not cause clinically significant inhibition of human CYP2C9, 2C19, 2D6, and 3A4 activities in vivo Sources: https://pubmed.ncbi.nlm.nih.gov/10348802/
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10348802/	no		no (co-administration study) Comment: Results show that single-dose disulfiram does not cause clinically significant inhibition of human CYP2C9, 2C19, 2D6, and 3A4 activities in vivo Sources: https://pubmed.ncbi.nlm.nih.gov/10348802/
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10348802/	no		no (co-administration study) Comment: Results show that single-dose disulfiram does not cause clinically significant inhibition of human CYP2C9, 2C19, 2D6, and 3A4 activities in vivo Sources: https://pubmed.ncbi.nlm.nih.gov/10348802/
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10348802/	no		no (co-administration study) Comment: Results show that single-dose disulfiram does not cause clinically significant inhibition of human CYP2C9, 2C19, 2D6, and 3A4 activities in vivo Sources: https://pubmed.ncbi.nlm.nih.gov/10348802/
CYP2E1 1146	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2993453/	yes [Ki 12.1 uM]	DCC 1
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11851639/; https://pubmed.ncbi.nlm.nih.gov/10078678/	yes		yes (co-administration study) Comment: Disulfiram, a selective inhibitor of human hepatic P450 2E1, prevented 80-90% of isoflurane metabolism Sources: https://pubmed.ncbi.nlm.nih.gov/11851639/; https://pubmed.ncbi.nlm.nih.gov/10078678/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4659	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4659
ChemicalBook	CB0476519	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0476519
eMolecules	28294932	https://www.emolecules.com/cgi-bin/more?vid=28294932
eMolecules	531942	https://www.emolecules.com/cgi-bin/more?vid=531942
MolPort	MolPort-001-792-519	https://www.molport.com/shop/molecule-link/MolPort-001-792-519
Selleck Chemicals	Disulfiram(Antabuse)	http://www.selleckchem.com/products/Disulfiram(Antabuse).html
ZINC	ZINC000001529266	http://zinc15.docking.org/substances/ZINC000001529266

PubMed

Title	Date	PubMed
Manic episode with psychosis following a lower than recommended dosage regimen of disulfiram.	2008-01-01	17904262
Behavioral couples therapy for comorbid substance use disorders and combat-related posttraumatic stress disorder among male veterans: an initial evaluation.	2008-01	17628345
Adverse effects of excessive nitric oxide on cytochrome c oxidase in lenses of hereditary cataract UPL rats.	2007-12-05	17936468
Disulfiram-induced transient optic and peripheral neuropathy: a case report.	2007-12	17786501
Quantity of ethanol absorption after excessive hand disinfection using three commercially available hand rubs is minimal and below toxic levels for humans.	2007-10-11	17927841
[Acute encephalopathy secondary to treatment with disulfiram].	2007-10-06	17918114
Perturbation of retinoic acid (RA)-mediated limb development suggests a role for diminished RA signaling in the teratogenesis of ethanol.	2007-09	17676605
Hypotension and ST depression as a result of disulfiram ethanol reaction.	2007-08	17620917
Disulfiram is an inhibitor of human purified monoacylglycerol lipase, the enzyme regulating 2-arachidonoylglycerol signaling.	2007-07-23	17579916
Induction of tibial dyschondroplasia by carbamate and thiocarbamate pesticides.	2007-06	17626489
Manic episode with psychotic symptoms associated with high dose of disulfiram: a case report.	2007-04	17414256
Naltrexone and disulfiram in patients with alcohol dependence and current depression.	2007-04	17414239
Disulfiram effects on responses to intravenous cocaine administration.	2007-03-16	16979847
Pharmacological profiling of disulfiram using human tumor cell lines and human tumor cells from patients.	2007-01-01	17026967
Refractive hypotension in a patient with disulfiram-ethanol reaction.	2007-01	17220694
Bench-to-bedside review: current evidence for extracorporeal albumin dialysis systems in liver failure.	2007	17567927
[Disulfiram-induced delirium: a case report].	2006-12	17313059
Disulfiram, a clinically used anti-alcoholism drug and copper-binding agent, induces apoptotic cell death in breast cancer cultures and xenografts via inhibition of the proteasome activity.	2006-11-01	17079463
Antabuse reaction with ceftin.	2006-11	17074964
[Optic neuropathy while taking disulfiram].	2006-10	17075509
Choosing the right medication for the treatment of alcoholism.	2006-10	16968619
Involvement of drug-specific T cells in acute drug-induced interstitial nephritis.	2006-10	16943303
The catatonic dilemma expanded.	2006-09-07	16959040
[New developments in the pharmacotherapy of cocaine dependence].	2006-09	16425053
Quantification of breath carbon disulphide and acetone following a single dose of disulfiram (Antabuse) using selected ion flow tube mass spectrometry (SIFT-MS).	2006-06	16800830
[Is Antabus therapy connected with reduced efficacy of nitroglycerin?].	2006-04-24	16674895
Transgenic analysis of the medaka mesp-b enhancer in somitogenesis.	2006-04	16573733
Clinical characteristics and prognostic markers in disulfiram-induced liver injury.	2006-04	16487618
Disulfiram irreversibly aggregates betaine aldehyde dehydrogenase--a potential target for antimicrobial agents against Pseudomonas aeruginosa.	2006-03-10	16426571
Cross-reactivity between thiurams.	2006-03	16524440
Effects of dopamine beta-hydroxylase genotype and disulfiram inhibition on catecholamine homeostasis in mice.	2005-11	16163519
[The first to go--physicians who experimented on themselves].	2005-09-08	16151505
Fulminant drug-induced hepatic failure leading to death or liver transplantation in Sweden.	2005-09	16165719
Effect of inducers of DT-diaphorase on the haemolytic activity and nephrotoxicity of 2-amino-1,4-naphthoquinone in rats.	2005-08-15	16045903
Disulfiram metabolites permanently inactivate the human multidrug resistance P-glycoprotein.	2005-07-21	16028354
Are alcoholism treatments effective? The Project MATCH data.	2005-07-14	16018798
Pharmacokinetics, safety, and tolerability of a depot formulation of naltrexone in alcoholics: an open-label trial.	2005-04-01	15804355
Acute liver failure: a message found under the skin.	2005-04	15811896
Cutaneous metabolism of glycol ethers.	2005-03	15551062
Resistance of zwitterionic telomers accumulated on metal surfaces against nonspecific adsorption of proteins.	2005-02-15	15589539
Clioquinol and pyrrolidine dithiocarbamate complex with copper to form proteasome inhibitors and apoptosis inducers in human breast cancer cells.	2005	16280039
[Anterior myocardial infarction in a chronic alcoholic man on disulfiram therapy: a case report].	2004-12	15709459
One-pot synthesis of high-quality zinc-blende CdS nanocrystals.	2004-11-10	15521736
Preparation of mononuclear and dinuclear Rh hydrotris(pyrazolyl)borato complexes containing arenethiolato ligands and conversion of the mononuclear complexes into dinuclear Rh-Rh and Rh-Ir complexes with bridging arenethiolato ligands.	2004-11-07	15510281
Ask the doctor. I need to quit drinking, but don't think I can do it on my own. Can I use a drug like Antabuse even though I have heart disease?	2004-10	15496370
Disulfiram is a potent modulator of multidrug transporter Cdr1p of Candida albicans.	2004-09-17	15325261
Disulfiram inhibits activating transcription factor/cyclic AMP-responsive element binding protein and human melanoma growth in a metal-dependent manner in vitro, in mice and in a patient with metastatic disease.	2004-09	15367699
Disulfiram-induced fulminant hepatic failure in an active duty soldier.	2004-08	15379082
Effectiveness of some means using against root rot on parsley seedling root.	2004	15756860
Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects.	1991-03-01	1664256

Patents

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:03 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:03 GMT 2025`
Record UNII	TR3MLJ1UAI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRAETHYLTHIOPEROXYDICARBONIC DIAMIDE ((((C(SUB 2)H(SUB 5))(SUB 2)N)C(S))(SUB 2)S(SUB 2))

Preferred Name

English

DISULFIRAM

Official Name

English

ORA102

Code

English

ANTABUSE

Brand Name

English

DISULFIRAM [HSDB]

Common Name

English

THIOPEROXYDICARBONIC DIAMIDE ((H2N)C(S))(SUB 2) S(SUB 2), TETRAETHYL-

Common Name

English

DISULFIRAM [MART.]

Common Name

English

DISULFIRAM [MI]

Common Name

English

Disulfiram [WHO-DD]

Common Name

English

ORA-102

Code

English

NSC-25953

Code

English

DISULFIRAM [JAN]

Common Name

English

disulfiram [INN]

Common Name

English

TETRAETHYLTHIURAM DISULPHIDE

Systematic Name

English

DISULFIRAM [EP IMPURITY]

Common Name

English

DISULFIRAM [VANDF]

Common Name

English

BIS(DIETHYLTHIOCARBAMOYL) DISULPHIDE

Systematic Name

English

TETRAETHYLTHIURAM DISULFIDE

Systematic Name

English

DISULFIRAM [ORANGE BOOK]

Common Name

English

DISULFIRAM [IARC]

Common Name

English

DISULFIRAM [USP MONOGRAPH]

Common Name

English

Bis(diethylthiocarbamoyl) disulfide

Systematic Name

English

DISULFIRAM [EP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN07BB01