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.

Label unavailable CHEBI:35489
Label unavailable 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

wikipedia.en:Disulfiram

Activity roles

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

fungicide 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	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`

Organism-specific examples
Protein	Gene	Organism	Entry
Replicase polyprotein 1ab `UniProtKB:P0DTD1` BindingDB target chain 1	—	Severe acute respiratory syndrome coronavirus 2 `NCBITaxon:2697049`	REVIEWED

PMID:32272481 (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.)

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
RESEEDED_FROM_SOURCES 2026-09-02 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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