N,N-diethyl[(diethylcarbamothioyl)disulfanyl]carbothioamide

• ChemBase ID: 701
• Molecular Formular: C10H20N2S4
• Molecular Mass: 296.5392
• Monoisotopic Mass: 296.05093265
• SMILES: S(SC(=S)N(CC)CC)C(=S)N(CC)CC
• Canonical SMILES: CCN(C(=S)SSC(=S)N(CC)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
• InChIKey: AUZONCFQVSMFAP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N,N-diethyl[(diethylcarbamothioyl)disulfanyl]carbothioamide
• IUPAC Traditional name: disulfiram
• Brand Name: Abstensil; Abstinil; Abstinyl; Accel Tet; Accel Tet-R; Akrochem Tetd; Alcophobin; Alk-Aubs; Ancazide Et; Antabus; Antabuse; Antadix; Antaenyl; Antaethan; Antaethyl; Antaetil; Antalcol; Antetan; Antethyl; Antetil; Anteyl; Anthethyl; Anti-Ethyl; Antiaethan; Anticol; Antietanol; Antietil; Antikol; Antivitium; Aversan; Averzan; Bonibal; Contralin; Contrapot; Cronetal; Dicupral; Disetil; Disulfan; Disulfram; Ekagom Dtet; Ekagom Teds; Ekagom Tetds; Ekaland Tetd; Ephorran; Espenal; Esperal; Etabus; Ethyl Thiram; Ethyl Thiudad; Ethyl Thiurad; Ethyl Tuads; Ethyl Tuads Rodform; Ethyl Tuex; Ethyldithiourame; Ethyldithiurame; Etyl Tuex; Exhoran; Exhorran; Gababentin; Hoca; Krotenal; Nocbin; Nocceler Tet; Nocceler Tet-G; Noxal; Perkacit Tetd; Perkait Tetd; Refusal; Ro-Sulfiram; Sanceler Tet; Sanceler Tet-G; Soxinol Tet; Stopaethyl; Stopethyl; Stopety; Stopetyl; Super Rodiatox; TTS; Tenurid; Tenutex; Tetidis; Tetradin; Tetradine; Tetraetil; Teturam; Teturamin; Thiocid; Thiophos; Thioscabin; Thireranide; Tillram; Tiuram; TTS X
• Synonyms: 1-(diethylthiocarbamoyldisulfanyl)-N,N-diethyl-methanethioamide; Tetraethylthiuram disulfide; Disulfiram; 1,1',1'',1'''-{Disulfanediylbis[(thioxomethylene)-nitrilo]}tetraethane; Bis(diethylthiocarbamoyl) disulfide; Bis(diethylthiocarbamyl) disulfide; Dupon 4472; Dupont Fungicide 4472; Disulfuram; Disulphuram; TATD; TETD; Tetraethylthioperoxydicarbonic Diamide; Tetraethylthiram Disulfide; Tetraethylthiram Disulphide; Tetraethylthiuram; Tetraethylthiuram Disulfide; Tetraethylthiuram Disulphide; Tetraethylthiuram Sulfide; Tetraethylthiuran Disulfide; TTD; Usaf B-33; Disulfiram; Antabuse; Antabus; 双(二乙基硫代氨基甲酰)二硫化物; 双硫仑; 双硫醒; 二硫化四乙基秋兰姆; 四乙基二硫化秋兰姆

Database IDs

• CAS Number: 97-77-8
• EC Number: 202-607-8
• MDL Number: MFCD00009048
• Beilstein Number: 1712560
• Merck Index: 143364
• PubChem SID: 46506008; 24278722; 160964164; 24888757
• PubChem CID: 3117
• CHEBI ID: 4659
• ATC CODE: P03AA04; N07BB01
• CHEMBL: 964
• Chemspider ID: 3005
• DrugBank ID: DB00822
• KEGG ID: D00131
• Unique Ingredient Identifier: TR3MLJ1UAI
• Wikipedia Title: Disulfiram
• Medline Plus: a682602

CALCULATED PROPERTIES

JChem

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.159759
• LogD (pH = 7.4): 4.159759
• Log P: 4.159759
• Molar Refractivity: 88.2352 cm^3
• Polarizability: 34.53991 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.88
• LOG S: -4.37
• Solubility (Water): 1.26e-02 g/l

PROPERTIES

Physical Property

• Solubility: 4.09 mg/L
• Melting Point: 69-71 °C(lit.); 69-72°C; 70 °C
• Boiling Point: 1.17 °C at 17 mmHg; 117°C/17mm
• Density: 1.30 (water = 1); 1.300
• Hydrophobicity(logP): 1.9

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: JO1225000
• European Hazard Symbols: Nature polluting (N); X; Harmful (Xn)
• UN Number: 2811; 3077; UN3077
• German water hazard class: 3
• Hazard Class: 6.1; 9
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 22-43-48/22-50/53; R:22-43-48/22-50/53
• Safety Statements: 24-37-60-61; S:24-37-60-61
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: false; 是
• GHS Pictograms: GHS07; GHS08; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317-H373-H410; H373-H400-H410-H302-H317
• GHS Precautionary statements: P260-P261-P280-P302+P352-P321-P501A; P273-P280-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3077 9/PG 3

Pharmacology Properties

• Admin Routes: Oral, subdermal implant
• Half Life: 60–120 hours
• Metabolism: Hepatic to diethylthiocarbamate
• Pregnancy Category: C (US)
• Gene Information: human ... ALDH2(217), CYP1A2(1544); human ... CYP1A2(1544)

Product Information

• Purity: ≥97%; ≥97.0% (S); 97%
• Salt Data: Free Base
• Linear Formula: (C2H5)2NCSS2CSN(C2H5)2

DETAILS

MP Biomedicals - 02150998

Crystalline
Dopamine β-hydroxylase inhibitor.

DrugBank - DB00822

• Drug Groups: approved
• Description: 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. [PubChem]
• Indication: For the treatment and management of chronic alcoholism
• Pharmacology: Disulfiram produces a sensitivity to alcohol which results in a highly unpleasant reaction when the patient under treatment ingests even small amounts of alcohol. Disulfiram blocks the oxidation of alcohol at the acetaldehyde stage during alcohol metabolism following disulfiram intake, the concentration of acetaldehyde occurring in the blood may be 5 to 10 times higher than that found during metabolism of the same amount of alcohol alone. Accumulation of acetaldehyde in the blood produces a complex of highly unpleasant symptoms referred to hereinafter as the disulfiram-alcohol reaction. This reaction, which is proportional to the dosage of both disulfiram and alcohol, will persist as long as alcohol is being metabolized. Disulfiram does not appear to influence the rate of alcohol elimination from the body. Prolonged administration of disulfiram does not produce tolerance; the longer a patient remains on therapy, the more exquisitely sensitive he becomes to alcohol.
• Toxicity: LD₅₀=8.6g/kg (orally in rats). Symptoms of overdose include irritation, slight drowsiness, unpleasant taste, mild GI disturbances, and orthostatic hypotension.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Disulfiram is absorbed slowly from the gastrointestinal tract (80 to 90% of oral dose).
• References: Nash T, Rice WG: Efficacies of zinc-finger-active drugs against Giardia lamblia. Antimicrob Agents Chemother. 1998 Jun;42(6):1488-92. [Pubmed] ; Bouma MJ, Snowdon D, Fairlamb AH, Ackers JP: Activity of disulfiram (bis(diethylthiocarbamoyl)disulphide) and ditiocarb (diethyldithiocarbamate) against metronidazole-sensitive and -resistant Trichomonas vaginalis and Tritrichomonas foetus. J Antimicrob Chemother. 1998 Dec;42(6):817-20. [Pubmed] ; Gaval-Cruz M, Weinshenker D: mechanisms of disulfiram-induced cocaine abstinence: antabuse and cocaine relapse. Mol Interv. 2009 Aug;9(4):175-87. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1680

Research Area: Neurological Disease
Biological Activity:
Disulfiram is an agent used to support the treatment of chronic alcoholism by producing an acute sensitivity to alcohol. Disulfiram is also being studied as a treatment for cocaine dependence, as it prevents the breakdown of dopamine (a neurotransmitter whose release is stimulated by cocaine); the excess dopamine results in increased anxiety, higher blood pressure, restlessness and other unpleasant symptoms. Several studies have reported that it has anti-protozoal activity as well. [1]

Sigma Aldrich - T1132

Application
乙醇脱氢酶抑制剂。
研究表明，双硫仑可作为原型，用于开发靶向 PKC 同工酶中氧化还原调控型 Cys 开关的新型防癌剂。Proceedings of the AACR，第45卷，2004 年 3 月。#2242

Sigma Aldrich - 86720

Application
Alcohol dehydrogenase inhibitor.
Packaging
1 kg in poly bottle
50, 250 g in poly bottle

REFERENCES

• Nash T, Rice WG: Efficacies of zinc-finger-active drugs against Giardia lamblia. Antimicrob Agents Chemother. 1998 Jun;42(6):1488-92. Pubmed
• Bouma MJ, Snowdon D, Fairlamb AH, Ackers JP: Activity of disulfiram (bis(diethylthiocarbamoyl)disulphide) and ditiocarb (diethyldithiocarbamate) against metronidazole-sensitive and -resistant Trichomonas vaginalis and Tritrichomonas foetus. J Antimicrob Chemother. 1998 Dec;42(6):817-20. Pubmed
• Gaval-Cruz M, Weinshenker D: mechanisms of disulfiram-induced cocaine abstinence: antabuse and cocaine relapse. Mol Interv. 2009 Aug;9(4):175-87. Pubmed
• http://en.wikipedia.org/wiki/Disulfiram