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Substance Name: Disulfiram [USP:INN:BAN:JAN]
RN: 97-77-8
UNII: TR3MLJ1UAI
InChIKey: AUZONCFQVSMFAP-UHFFFAOYSA-N

Note

  • 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. When alcohol is ingested after administration of disulfiram, blood acetaldehyde concentrations are increased, followed by flushing, systemic vasodilation, respiratory difficulties, nausea, hypotension, and other symptoms (acetaldehyde syndrome). It acts by inhibiting aldehyde dehydrogenase.

Molecular Formula

  • C10-H20-N2-S4

Molecular Weight

  • 296.546
 

Classification Codes

Classification Codes

  • Acaricide
  • Acetaldehyde Dehydrogenase Inhibitors
  • Agricultural Chemical
  • Alcohol Deterrent
  • Alcohol Deterrents
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Fungicide, Bactericide, Wood Preservative
  • Human Data
  • Immunomodulator
  • Mutation Data
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data

Superlist Classification Codes

  • Overall Carcinogenic Evaluation: Group 3
  • TWA 2 mg/m3; Not classifiable as a human carcinogen

Names and Synonyms

Name of Substance

  • Disulfiram
  • Disulfiram [USP:INN:BAN:JAN]

MeSH Heading

  • Disulfiram

Synonyms

  • 1,1'-Dithiobis(N,N-diethylthioformamide)
  • Abstensil
  • Abstensyl (Argentina)
  • Abstinil
  • Abstinyl
  • Accel TET
  • Accel TET-R
  • AI3-27340
  • Alcophobin
  • Alk-aubs
  • Antabus
  • Antabuse
  • Antadix
  • Antaenyl
  • Antaethyl
  • Antaetil
  • Antalcol
  • Antetan
  • Antetil
  • Anteyl
  • Anti-ethyl
  • Antiaethan
  • Anticol
  • Antietanol
  • Antietil
  • Antikol
  • Antivitium
  • Antivitium (Spain)
  • Aversan
  • Averzan
  • Bis((diethylamino)thioxomethyl) disulfide
  • Bis((diethylamino)thioxomethyl)disulphide
  • Bis(diethylthiocarbamoyl) disulfide
  • Bis(diethylthiocarbamoyl)disulphide
  • Bis(N,N-diethylthiocarbamoyl) disulfide
  • Bis(N,N-diethylthiocarbamoyl)disulphide
  • Bonibal
  • CCRIS 582
  • Contralin
  • Contrapot
  • Cronetal
  • Dicupral
  • Disetil
  • Disulfan
  • Disulfiram
  • Disulfirame
  • Disulfirame [DCIT]
  • Disulfiramo
  • Disulfiramo [INN-Spanish]
  • Disulfiramum
  • Disulfiramum [INN-Latin]
  • Dupon 4472
  • Dupont fungicide 4472
  • EC 202-607-8
  • EINECS 202-607-8
  • Ekagom DTET
  • Ekagom TEDS
  • Ekagom TETDS
  • ENT 27,340
  • Ephorran
  • Esperal
  • Esperal [France]
  • Etabus
  • Ethyl thiram
  • Ethyl thiurad
  • Ethyl tuads
  • Ethyl TUEX
  • Ethyldithiourame
  • Ethyldithiurame
  • Exhorran
  • Formamide, 1,1'-dithiobis(N,N-diethylthio-
  • HOCA
  • Hocakrotenalnci-C02959
  • HSDB 3317
  • Krotenal
  • N,N,N',N'-Tetraethylthiuram disulfide
  • N,N,N',N'-Tetraethylthiuram disulphide
  • NCI-C02959
  • Nocbin
  • Nocceler TET
  • Nocceler TET-G
  • Noxal
  • Noxal (VAN)
  • NSC 190940
  • NSC 25953
  • Refusal
  • Refusal [Netherlands]
  • Ro-Sulfiram
  • Ro-Sulfram-500 (USA)
  • Sanceler TET
  • Sanceler TET-G
  • Soxinol TET
  • Stopetyl
  • TATD
  • Tenurid
  • Tenutex
  • TETD
  • Tetidis
  • Tetradine
  • Tetraethylthioperoxydicarbonic diamide
  • Tetraethylthiram disulfide
  • Tetraethylthiram disulphide
  • Tetraethylthiuram disulfide
  • Tetraethylthiuram disulphide
  • Tetraethylthiuran disulfide
  • Tetraethylthiurium disulfide
  • Tetraetil
  • Teturam
  • Teturamin
  • Thioperoxydicarbonic diamide ((H2N)C(S))2S2, tetraethyl-
  • Thiosan
  • Thioscabin
  • Thiuram disulfide, tetraethyl-
  • Thiuram E
  • Thiuranide
  • Tiuram
  • TTD
  • TTS [Alcohol deterrent]
  • Tuads, ethyl
  • UNII-TR3MLJ1UAI
  • USAF B-33

Systematic Names

  • Disulfide, bis(diethylthiocarbamoyl)
  • Disulfiram
  • Thioperoxydicarbonic diamide (((H2N)C(S))2S2), N,N,N',N'-tetraethyl-
  • Thioperoxydicarbonic diamide (((H2N)C(S))2S2), tetraethyl-

Superlist Names

  • Disulfide, bis(diethylthiocarbamoyl)
  • Disulfiram
  • Tetraethylthiuram disulfide
  • Tetraethylthiuram disulphide
  • Thioperoxydicarbonic diamide, tetraethyl-

Registry Numbers

CAS Registry Number

  • 97-77-8

FDA UNII

  • TR3MLJ1UAI

Other Registry Numbers

  • 11078-22-1
  • 155-01-1

System Generated Number

  • 0000097778

Structure Descriptors

InChI

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

InChIKey

AUZONCFQVSMFAP-UHFFFAOYSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 150mg/kg (150mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 230, 1969.
dog LDLo oral 3500mg/kg (3500mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: ATAXIA
Acta Pharmacologica et Toxicologica. Vol. 8, Pg. 305, 1952.
human LDLo oral 160mg/kg (160mg/kg) BEHAVIORAL: COMA

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE

LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"
British Medical Journal. Vol. 2, Pg. 94, 1977.
man LDLo oral 150mg/kg/6W-I (150mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" Archives of Internal Medicine. Vol. 143, Pg. 1271, 1983.
man TDLo oral 150mg/kg/6W-I (150mg/kg) MUSCULOSKELETAL: JOINTS Arthritis and Rheumatism. Vol. 25, Pg. 1494, 1982.
man TDLo oral 450mg/kg/6W-I (450mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

BRAIN AND COVERINGS: ENCEPHALITIS

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"
American Journal of Gastroenterology. Vol. 93, Pg. 830, 1998.
mouse LD50 intraperitoneal 75mg/kg (75mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 oral 1980mg/kg (1980mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 112, Pg. 36, 1957.
mouse LD50 subcutaneous 2600mg/kg (2600mg/kg)   Drugs in Japan Vol. -, Pg. 523, 1995.
rabbit LD50 oral 1800mg/kg (1800mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: ATAXIA
Acta Pharmacologica et Toxicologica. Vol. 8, Pg. 305, 1952.
rat LD subcutaneous > 4gm/kg (4000mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 8, Pg. 305, 1952.
rat LD50 intraperitoneal 248mg/kg (248mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Journal de Pharmacologie. Vol. 9, Pg. 35, 1978.
rat LD50 oral 500mg/kg (500mg/kg)   Archiv fuer Toxikologie. Vol. 22, Pg. 12, 1966.
women LDLo oral 90mg/kg/18D-I (90mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

BEHAVIORAL: COMA
Deutsche Medizinische Wochenschrift. Vol. 118, Pg. 1355, 1993.
women TDLo oral 90mg/kg/18D-I (90mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" Journal of Clinical Psychiatry. Vol. 46, Pg. 67, 1985.
women TDLo oral 140mg/kg/2W (140mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Southern Medical Journal. Vol. 80, Pg. 1577, 1987.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 71.5 deg C   EXP
log P (octanol-water) 3.88 (none)   EXP
Water Solubility 4.09 mg/L 25 EXP
Vapor Pressure 8.70E-04 mm Hg 25 EST
Henry's Law Constant 8.32E-05 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.92E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.