disulfiram

CHEBI:4659 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

An organic disulfide that results from the formal oxidative dimerisation of N,N-diethyldithiocarbamic acid. A multi-enzyme inhibitor that is used in alcohol aversion therapy and also exhibits anticancer properties. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:35489 CHEBI:35489
CHEBI:39298 CHEBI:39298

Chemical structure

Computed structure properties
Molecular formula	C10H20N2S4
Charge	0
Average mass	296.552 Da
Monoisotopic mass	296.05093 Da
Source	ChEBI
InChIKey	AUZONCFQVSMFAP-UHFFFAOYSA-N

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

Also called

1,1',1'',1'''-[disulfanediylbis(carbonothioylnitrilo)]tetraethane (EXACT_SYNONYM)— chebi
1,1'-dithiobis(N,N-diethylthioformamide) (EXACT_SYNONYM)— chebi
Antabuse (EXACT_SYNONYM)— chebi
Disulfiram (EXACT_SYNONYM)— chebi
N,N,N',N'-tetraethylthiuram disulfide (EXACT_SYNONYM)— chebi
Tetraethylthiuram disulfide (EXACT_SYNONYM)— chebi
bis(diethylthiocarbamoyl) disulfide (EXACT_SYNONYM)— chebi
tetraethylthioperoxydicarbonic diamide (EXACT_SYNONYM)— chebi
tetraethylthiuram disulfide (EXACT_SYNONYM)— chebi
tetraethylthiuram disulphide (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:97-77-8
drugbank:DB00822
drugcentral:928
hmdb:HMDB0014960
kegg.compound:C01692
kegg.drug:D00131
lincs.smallmolecule:LSM-5467
metacyc.compound:DISULFIRAM
pesticides:disulfiram
reaxys:1712560
wikipedia.en:Disulfiram

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:24127 CHEBI:24127

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:4659`	disulfiram	`antibioticmech:chebi-5dccdffd2e`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

Replicase polyprotein 1ab VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).

Severe acute respiratory syndrome coronavirus 2 NCBITaxon:2697049

Quantitative measurements
Type	Reported value	Assay	BindingDB IDs	Reference
IC50	9350 nM	high-throughput activity assay Recombinant SARS-CoV-2 Mpro with native N and C termini was expressed in Escherichia coli, and subsequently purified (Extended Data Fig. 1a, b). The molecular mass of SARS-CoV-2 Mpro as determined by mass spectroscopy is 33797.0 Da, consistent with its theoretical molecular mass of 33796.8 Da. To characterize the enzymatic activity of SARS-CoV-2 Mpro and to carry out high-throughput screening of inhibitors, we developed a fluorescence resonance energy transfer assay. To do this, we designed and synthesized the fluorescently labelled substrate Mca AVLQ↓SGFRK(Dnp)K, derived from the N-terminal autocleavage sequence of the viral protease, for time-dependent kinetic analysis (Extended Data Fig. 1e). The catalytic efficiency (kcat/Km) for SARS-CoV-2 Mpro was measured to be 28,500 M−1 s−1, which is slightly higher than that for SARS-CoV Mpro (kcat/Km = 26,500 M−1 s−1)10 and more than 30-fold higher than that of human rhinovirus 3C protease (kcat/Km = 920 M−1 s−1).	`RSID 840118` `assay 8774_1` `monomer 50058655`	`PMID:32272481`
IC50	9350 nM	No assay is provided This is a review article.	`RSID 868913` `assay 8918_1` `monomer 50058655`	`PMID:32852058`
IC50	220 nM	Hit profiling assay without DTT Primary assay principle based on quenched FRET peptide substrate of SARS-CoV-2 3CL-Pro (lhs). Inhibiting compounds reduce fluorescence signal relative to DMSO controls. Hit profiling using X-ray. Substrate turnover was directly proportional to enzyme concentrations up to 60 nM and assay incubation times up to 15 minutes post substrate addition.	`RSID 902203` `assay 9114_1` `monomer 50058655`	`DOI:10.1101/2020.12.16.422677`
IC50	9350 nM	Various Assay This is a review article. Please point to the original journal.	`RSID 1074058` `assay 10079_1` `monomer 50058655`	`PMID:34798775`
KI	3710 nM	Various Assay This is a review article. Please point to the original journal.	`RSID 1074059` `assay 10079_1` `monomer 50058655`	`PMID:34798775`

Organism-specific examples
Protein	Gene	Organism	Entry
Replicase polyprotein 1ab `UniProtKB:P0DTD1`	—	Severe acute respiratory syndrome coronavirus 2	REVIEWED

PMID:32272481 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
PMID:32852058 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
DOI:10.1101/2020.12.16.422677 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)
PMID:34798775 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)

Mechanism summary

Clinical status: APPROVED

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.