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Chemistry

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Also known as: Tetraethylthiuram disulfide, 97-77-8, Antabuse, Bis(diethylthiocarbamoyl) disulfide, Antabus, Tetd
Molecular Formula
C10H20N2S4
Molecular Weight
296.5  g/mol
InChI Key
AUZONCFQVSMFAP-UHFFFAOYSA-N
FDA UNII
TR3MLJ1UAI

Sulfiram
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.
Disulfiram is an Aldehyde Dehydrogenase Inhibitor. The mechanism of action of disulfiram is as an Acetyl Aldehyde Dehydrogenase Inhibitor.
1 2D Structure

Sulfiram

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
diethylcarbamothioylsulfanyl N,N-diethylcarbamodithioate
2.1.2 InChI
InChI=1S/C10H20N2S4/c1-5-11(6-2)9(13)15-16-10(14)12(7-3)8-4/h5-8H2,1-4H3
2.1.3 InChI Key
AUZONCFQVSMFAP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCN(CC)C(=S)SSC(=S)N(CC)CC
2.2 Other Identifiers
2.2.1 UNII
TR3MLJ1UAI
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Alcophobin

2. Antabus

3. Antabuse

4. Anticol

5. Bis(diethylthiocarbamoyl) Disulfide

6. Dicupral

7. Disulfide, Tetraethylthiuram

8. Esperal

9. Tetraethylthioperoxydicarbonic Diamide, ((h2n)c(s))2s2

10. Tetraethylthiuram Disulfide

11. Teturam

2.3.2 Depositor-Supplied Synonyms

1. Tetraethylthiuram Disulfide

2. 97-77-8

3. Antabuse

4. Bis(diethylthiocarbamoyl) Disulfide

5. Antabus

6. Tetd

7. Alcophobin

8. Anticol

9. Esperal

10. Teturam

11. Dicupral

12. Exhorran

13. Hoca

14. Ethyldithiurame

15. Abstensil

16. Antaethyl

17. Antietanol

18. Antivitium

19. Contralin

20. Tetradine

21. Tetraetil

22. Teturamin

23. Abstinil

24. Abstinyl

25. Antadix

26. Antalcol

27. Antetan

28. Antetil

29. Antietil

30. Antikol

31. Aversan

32. Averzan

33. Cronetal

34. Krotenal

35. Refusal

36. Etabus

37. Ethyl Tuads

38. Ethyl Thiram

39. Ethyl Thiurad

40. Ethyl Tuex

41. Antaenyl

42. Antaetil

43. Antiaethan

44. Contrapot

45. Disulfan

46. Disulfuram

47. Ephorran

48. Stopetyl

49. Thiuranide

50. Anteyl

51. Bonibal

52. Disetil

53. Nocbin

54. Tenurid

55. Tenutex

56. Tetidis

57. Ekagom Teds

58. Ekagom Tetds

59. Ethyldithiourame

60. Noxal

61. Anti-ethyl

62. Alk-aubs

63. Tetraethylthiuram Disulphide

64. Thiuram E

65. Tatd

66. Soxinol Tet

67. Tetraethylthiram Disulfide

68. Ekagom Dtet

69. Accel Tet

70. Espenal

71. Exhoran

72. Sanceler Tet-g

73. Ro-sulfiram

74. Tetraethylthiuram

75. Tuads, Ethyl

76. Usaf B-33

77. Sanceler Tet

78. Tetraethylthioperoxydicarbonic Diamide

79. Stopaethyl

80. Thireranide

81. Antaethan

82. Antethyl

83. Tetradin

84. Tillram

85. Accel Tet-r

86. Ethyl Thiudad

87. Dupon 4472

88. Tetraethylthiuran Disulfide

89. Anthethyl

90. Disulphuram

91. Dupont Fungicide 4472

92. Hocakrotenalnci-c02959

93. Tetraethylthiram Disulphide

94. Bis(diethylthiocarbamyl) Disulfide

95. Tetraethylthiuram Sulfide

96. Thiuram Disulfide, Tetraethyl-

97. N,n,n',n'-tetraethylthiuram Disulfide

98. Antabuse (tn)

99. Bis(n,n-diethylthiocarbamoyl) Disulfide

100. 1,1'-dithiobis(n,n-diethylthioformamide)

101. Disulfide, Bis(diethylthiocarbamoyl)

102. Diethylcarbamothioylsulfanyl N,n-diethylcarbamodithioate

103. Ent 27,340

104. Nsc 190940

105. Thioperoxydicarbonic Diamide, Tetraethyl-

106. Bis(diethylthiocarbamoyl)disulphide

107. Nci-c02959

108. Tts

109. Nsc-25953

110. Bis(n,n-diethylthiocarbamoyl)disulphide

111. N,n,n',n'-tetraethylthiuram Disulphide

112. Bis((diethylamino)thioxomethyl)disulphide

113. Bis((diethylamino)thioxomethyl) Disulfide

114. Tetraethylthiuram Disulfide;tetd

115. Disulfiram (antabuse)

116. Tr3mlj1uai

117. N,n-diethyl[(diethylcarbamothioyl)disulfanyl]carbothioamide

118. Thioperoxydicarbonic Diamide ([(h2n)c(s)]2s2), Tetraethyl-

119. Chembl964

120. Mls000069818

121. Chebi:4659

122. Ora102

123. Ora-102

124. Bis(diethylthiocarbamyoyl)disulfide

125. 1,1',1'',1'''-[disulfanediylbis(carbonothioylnitrilo)]tetraethane

126. Nsc25953

127. Esperal [france]

128. Cas-97-77-8

129. Ncgc00016000-08

130. Ncgc00016000-13

131. Smr000059171

132. Thioperoxydicarbonic Diamide (((h2n)c(s))2s2), Tetraethyl-

133. Dsstox_cid_1322

134. Ancazide Et

135. Akrochem Tetd

136. Perkacit Tetd

137. Ekaland Tetd

138. Perkait Tetd

139. Dsstox_rid_76082

140. Dsstox_gsid_21322

141. Ethyl Tuads Rodform

142. C10h20n2s4

143. Disulfiramum [inn-latin]

144. Disulfiramo [inn-spanish]

145. Bis[(diethylamino)thioxomethyl] Disulfide

146. Ccris 582

147. 1,1'-dithiobis[n,n-diethylthioformamide]

148. Hsdb 3317

149. Sr-01000076145

150. Unii-tr3mlj1uai

151. Einecs 202-607-8

152. Mfcd00009048

153. Nsc 25953

154. Disulfarim

155. Ai3-27340

156. Formamide, 1,1'-dithiobis(n,n-diethylthio-

157. Thioperoxydicarbonic Diamide (((h2n)c(s))2s2), N,n,n',n'-tetraethyl-

158. Thioperoxydicarbonic Diamide ([(h2n)c(s)]2s2), N,n,n',n'-tetraethyl-

159. Disulfiram [usp:inn:ban:jan]

160. Prestwick_182

161. Spectrum_001010

162. Cpd000059171

163. Disulfiram [mi]

164. Opera_id_224

165. Disulfiram [inn]

166. Disulfiram [jan]

167. Prestwick0_000097

168. Prestwick1_000097

169. Prestwick2_000097

170. Prestwick3_000097

171. Spectrum2_001176

172. Spectrum3_000405

173. Spectrum4_000228

174. Spectrum5_001590

175. Disulfiram [hsdb]

176. Disulfiram [iarc]

177. Lopac-t-1132

178. 1,n-diethylthioformamide]

179. Disulfiram [vandf]

180. Formamide, 1,1'-dithiobis(n,n-diethylthio)-

181. Upcmld-dp090

182. Ec 202-607-8

183. T 1132

184. Tetraethyl Thiuram Disulfide

185. Disulfiram [mart.]

186. Tetraethyldithiuram Disulfide

187. Disulfiram [who-dd]

188. Lopac0_001164

189. Schembl27213

190. Bspbio_000054

191. Bspbio_001930

192. Kbiogr_000895

193. Kbioss_001490

194. Mls000758264

195. Mls001076475

196. Mls001423963

197. Spectrum1500262

198. Spbio_001191

199. Spbio_001993

200. Bpbio1_000060

201. Disulfiram (jp17/usp/inn)

202. Gtpl7168

203. Disulfiram [ep Impurity]

204. Disulfiram [orange Book]

205. Dtxsid1021322

206. Upcmld-dp090:001

207. Kbio2_001490

208. Kbio2_004058

209. Kbio2_006626

210. Kbio3_001150

211. Disulfiram [ep Monograph]

212. Thioperoxydicarbonic Diamide ((h2n)c(s))2s2, Tetraethyl-

213. Disulfiram [usp Monograph]

214. Hms1568c16

215. Hms1920i16

216. Hms2051m17

217. Hms2090c18

218. Hms2091o22

219. Hms2095c16

220. Hms2230k06

221. Hms3263j09

222. Hms3371b21

223. Hms3393m17

224. Hms3655i19

225. Hms3712c16

226. Hms3867h13

227. Pharmakon1600-01500262

228. Bcp07331

229. Hy-b0240

230. Zinc1529266

231. Bis-(diethyl-thiocarbamyl)-disulfide

232. Tox21_110280

233. Tox21_300403

234. Tox21_400072

235. Tox21_501164

236. Bdbm50058655

237. Ccg-39549

238. Dl-379

239. N,n',n'-tetraethylthiuram Disulfide

240. Nsc756748

241. Nsc800739

242. S1680

243. Stl069539

244. 1,1',1'',1'''-{disulfanediylbis[(thioxomethylene)-nitrilo]}tetraethane

245. Akos000120201

246. Tox21_110280_1

247. At13284

248. Db00822

249. Hs-0057

250. Lp01164

251. Nc00063

252. Nsc-756748

253. Nsc-800739

254. Sdccgsbi-0051131.p005

255. Wln: 2n2 & Yus & S 2

256. Ncgc00016000-01

257. Ncgc00016000-02

258. Ncgc00016000-03

259. Ncgc00016000-04

260. Ncgc00016000-05

261. Ncgc00016000-06

262. Ncgc00016000-07

263. Ncgc00016000-09

264. Ncgc00016000-10

265. Ncgc00016000-11

266. Ncgc00016000-12

267. Ncgc00016000-14

268. Ncgc00016000-15

269. Ncgc00016000-18

270. Ncgc00016000-29

271. Ncgc00094423-01

272. Ncgc00094423-02

273. Ncgc00094423-03

274. Ncgc00094423-05

275. Ncgc00094423-06

276. Ncgc00094423-07

277. Ncgc00254447-01

278. Ncgc00261849-01

279. N,n,n'',n''-tetraethylthiuram Disulfide

280. Bis(diethylthiocarbamoyl) Disulphide

281. Formamide,1'-dithiobis(n,n-diethylthio)-

282. Sbi-0051131.p004

283. 1,1''-dithiobis(n,n-diethylthioformamide)

284. Db-057683

285. Ab00051976

286. B0479

287. Eu-0101164

288. Ft-0631502

289. Ft-0667720

290. Sw196492-4

291. Tetraethylthiuram Disulfide, >=97.0% (s)

292. C01692

293. D00131

294. S00294

295. Ab00051976-20

296. Ab00051976-21

297. Ab00051976-23

298. Ab00051976_22

299. Ab00051976_25

300. A845750

301. Q409665

302. Q-201812

303. Sr-01000076145-1

304. Sr-01000076145-5

305. Sr-01000076145-8

306. Brd-k32744045-001-05-6

307. Brd-k32744045-001-17-1

308. Z1522553469

309. Disulfiram, British Pharmacopoeia (bp) Reference Standard

310. Disulfiram, European Pharmacopoeia (ep) Reference Standard

311. 1,1',1'',1'''-[disulfanediylbis(carbonothioylnitrilo)]tetra

312. Disulfiram, United States Pharmacopeia (usp) Reference Standard

313. 1,1'',1'''',1''''''-[disulfanediylbis(carbonothioylnitrilo)]tetraethane

314. Disulfiram, Pharmaceutical Secondary Standard; Certified Reference Material

315. N,n-diethylcarbamodithioic Acid [[diethylamino(sulfanylidene)methyl]thio] Ester

316. Thioperoxydicarbonic Diamide ((h2n)c(s))(sub 2) S(sub 2), Tetraethyl-

317. Tetraethylthioperoxydicarbonic Diamide ((((c(sub 2)h(sub 5))(sub 2)n)c(s))(sub 2)s(sub 2))

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 296.5 g/mol
Molecular Formula C10H20N2S4
XLogP33.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Exact Mass296.05093334 g/mol
Monoisotopic Mass296.05093334 g/mol
Topological Polar Surface Area121 Ų
Heavy Atom Count16
Formal Charge0
Complexity201
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameAntabuse
PubMed HealthDisulfiram (By mouth)
Drug ClassesEthanol Dependency
Drug LabelDisulfiram is an alcohol antagonist drug. CHEMICAL NAME:bis(diethylthiocarbamoyl) disulfide.STRUCTURAL FORMULA:C10H20N2S4 M.W. 296.54Disulfiram occurs as a white to off-white, odorless, and almost tasteless powder, soluble in water to the extent of a...
Active IngredientDisulfiram
Dosage FormTablet
RouteOral
Strength250mg; 500mg
Market StatusPrescription
CompanyOdyssey Pharms

2 of 4  
Drug NameDisulfiram
PubMed HealthDisulfiram (By mouth)
Drug ClassesEthanol Dependency
Drug LabelDisulfiram is an alcohol antagonist drug. CHEMICAL NAME: bis(diethylthiocarbamoyl) disulfide. STRUCTURAL FORMULA:Disulfiram occurs as a white to off-white, odorless, and almost tasteless powder, soluble in water to the extent of about 20 mg in 100 mL...
Active IngredientDisulfiram
Dosage FormTablet
RouteOral
Strength250mg; 500mg
Market StatusPrescription
CompanyVintage Pharms; Sigmapharm Labs; Roxane; Alvogen Pine Brook

3 of 4  
Drug NameAntabuse
PubMed HealthDisulfiram (By mouth)
Drug ClassesEthanol Dependency
Drug LabelDisulfiram is an alcohol antagonist drug. CHEMICAL NAME:bis(diethylthiocarbamoyl) disulfide.STRUCTURAL FORMULA:C10H20N2S4 M.W. 296.54Disulfiram occurs as a white to off-white, odorless, and almost tasteless powder, soluble in water to the extent of a...
Active IngredientDisulfiram
Dosage FormTablet
RouteOral
Strength250mg; 500mg
Market StatusPrescription
CompanyOdyssey Pharms

4 of 4  
Drug NameDisulfiram
PubMed HealthDisulfiram (By mouth)
Drug ClassesEthanol Dependency
Drug LabelDisulfiram is an alcohol antagonist drug. CHEMICAL NAME: bis(diethylthiocarbamoyl) disulfide. STRUCTURAL FORMULA:Disulfiram occurs as a white to off-white, odorless, and almost tasteless powder, soluble in water to the extent of about 20 mg in 100 mL...
Active IngredientDisulfiram
Dosage FormTablet
RouteOral
Strength250mg; 500mg
Market StatusPrescription
CompanyVintage Pharms; Sigmapharm Labs; Roxane; Alvogen Pine Brook

4.2 Therapeutic Uses

Alcohol Deterrents; Enzyme Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Disulfiram is used to help maintain sobriety in the treatment of chronic alcoholism in conjunction with supportive and psychotherapeutic measures.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1133


Case reports suggest that disulfiram may be useful for the treatment of nickel dermatitis. However, small double-blind placebo-controlled study of patients with hand eczema and nickel allergy did not find a clinically significant difference between those treated with disulfiram and those treated with placebo. Because some patients worsen with this therapy and because patients treated for nickel dermatitis have developed disulfiram induced hepatitis, this therapy is not generally indicated.

Goldfrank, L.R. (ed). Goldfrank's Toxicologic Emergencies. 7th Edition McGraw-Hill New York, New York 2002., p. 977


The oral efficacy of several chelating drugs, incl disulfiram, was studied in relation to their ability to prevent lethality due to acute inhalation exposure to nickel carbonyl. Disulfiram resulted in very high, but transient, plasma levels. Small, repeated oral doses of disulfiram would be just as effective in nickel carbonyl poisoning as a single large dithiocarb dose. However, disulfiram increase the nickel retained in brain tissue, possibly accounting for its limited efficacy. Caution in the use of oral disulfiram in human nickel carbonyl intoxication is recommended.

PMID:6293022 Baselt RC, Hanson VW; Res Commun Chem Pathol Pharmacol 38 (1): 113-24 (1982)


4.3 Drug Warning

... Alarming reactions may result from the ingestion of even small amt of alc in persons being treated with disulfiram. Marked resp depression, cardiovascular collapse, cardiac arrhythmias, myocardial infarction, acute congestive heart failure, unconsciousness, convulsions, and sudden and unexplained fatalities have occurred.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 388


The ingestion of alcohol by individuals previously treated with disulfiram gives rise to marked signs and symptoms. Within about 5-10 min face feels hot, and soon afterwards it is flushed and scarlet in appearance. As vasodilatation spreads over whole body, intense throbbing is felt in head and neck, and a pulsating headache may develop. Respiratory difficulties, nausea, copious vomiting, sweating, thirst, chest pain, considerable hypotension, orthostatic syncope, marked uneasiness, weakness, vertigo, blurred vision, and confusion are observed. Facial flush is replaced by pallor, and blood pressure may fall to shock level.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 441


May decrease urinary vanilmandelic acid excretion, although ... not sufficient to interfere with diagnosis of pheochromocytoma. /Disulfiram's/ inhibition of dopamine hydroxylase ... may increase urinary concn of homovanillic acid /adverse effect, oral/

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1977


Patients receiving disulfiram should be warned to avoid cough syrups, sauces, vinegars, elixirs, and other preparations that contain alcohol. External application of alcoholic liniments or lotions, including aftershave or back rub, may be sufficient to produce a disulfiram-alcohol reaction. Patients should be cautioned that disulfiram-alcohol reactions may occur for several weeks after discontinuance of disulfiram.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 3558


For more Drug Warnings (Complete) data for DISULFIRAM (17 total), please visit the HSDB record page.


4.4 Drug Indication

For the treatment and management of chronic alcoholism


5 Pharmacology and Biochemistry
5.1 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.


5.2 MeSH Pharmacological Classification

Acetaldehyde Dehydrogenase Inhibitors

Compounds that bind to and inhibit the enzymatic activity of acetaldehyde dehydrogenases. (See all compounds classified as Acetaldehyde Dehydrogenase Inhibitors.)


Alcohol Deterrents

Substances interfering with the metabolism of ethyl alcohol, causing unpleasant side effects thought to discourage the drinking of alcoholic beverages. Alcohol deterrents are used in the treatment of alcoholism. (See all compounds classified as Alcohol Deterrents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DISULFIRAM
5.3.2 FDA UNII
TR3MLJ1UAI
5.3.3 Pharmacological Classes
Aldehyde Dehydrogenase Inhibitor [EPC]; Acetyl Aldehyde Dehydrogenase Inhibitors [MoA]
5.4 ATC Code

N07BB01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


N - Nervous system

N07 - Other nervous system drugs

N07B - Drugs used in addictive disorders

N07BB - Drugs used in alcohol dependence

N07BB01 - Disulfiram


P - Antiparasitic products, insecticides and repellents

P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents

P03A - Ectoparasiticides, incl. scabicides

P03AA - Sulfur containing products

P03AA04 - Disulfiram


5.5 Absorption, Distribution and Excretion

Absorption

Disulfiram is absorbed slowly from the gastrointestinal tract (80 to 90% of oral dose).


Absorption /of disulfiram is/ slow. Eighty to ninety percent of an oral dose is absorbed. /Its/ biotransformation /is predominately/ hepatic /and/ a single dose will begin to affect ethanol metabolism within 1 to 2 hours.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1133


Disulfiram is ... completely absorbed from the human GI tract. However, a period of 12 hr is required for its full action, perhaps because, being highly sol in lipid, it is initially localized in fat. Elimination is relatively slow, and about 1/5 still remains in body at end of a week. The greater part of the absorbed drug is ... excreted in the urine as the sulfate, partly free and partly esterified.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 388


After a single oral dose of 50, 100, 200, or 400 mg/kg, disulfiram was found in dose-dependent quantities in blood, liver, kidney, spleen, brain, muscle, and peri-epididymal adipose tissue of rats. After a 2-mo treatment, accumulation was not dose-dependent, suggesting a saturation point for various organs.

De Saint-Blanquat G et al; Eur J Drug Metab Pharmacokinet 3 (4): 205-9 (1978)


The human plasma protein binding characteristics of disulfiram and its therapeutically active metabolite, diethylthiocarbamic acid methyl ester were investigated. Both compounds were bound principally to albumin over the ranges 200-800 and 345-2756 nM, respectively. The average number of binding sites was approximately one for both substances, whereas the average association constants were 7.1X10+4 and 6.1X10+3/M, respectively.

PMID:1982309 Johansson B; J Pharm Pharmacol 42 (Nov): 806-7 (1990)


For more Absorption, Distribution and Excretion (Complete) data for DISULFIRAM (7 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Hepatic.


Disulfiram is slowly metabolized in the liver to diethyldithiocarbamate, diethylamine, and carbon disulfide. Six hr after oral administration of the drug, one third of plasma disulfiram is in the form of diethyldithiocarbamate.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2005. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2005 (Plus Supplements)., p. 3559


In rats the following metabolites of disulfiram were found: diethyldithiocarbamate; diethyldithiocarbamate s-glucuronide; inorganic sulfate; diethylamine and carbon disulfide. A small amount of S was bound to proteins as mixed disulfides. ... Metabolism of disulfiram in man is similar to that in animals.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V12 89 (1976)


Recently, n,n-diethylthiocarbamoyl-1-thio-beta-glucopyranosiduronic acid was isolated from combined urine of 4 men given oral doses of tetraethylthiuram disulfide.

Menzie, C.M. Metabolism of Pesticides. U.S. Department of the Interior, Bureau of Sport Fisheries and Wildlife, Publication 127. Washington, DC: U.S. Government Printing Office, 1969., p. 331


Diethylthiocarbamic acid methyl ester, in contrast to other disulfiram metabolites, is a potent inhibitor of liver aldehyde dehydrogenase in vitro. Like disulfiram, diethylthiocarbamic acid methyl ester had a pronounced hypothermic effect in rats. This hypothermic effect and the augmented blood pressure response to ethanol challenge in rats developed rapidly with diethylthiocarbamic acid methyl ester but were somewhat delayed with disulfiram. The blood pressure response outlasted the presence of diethylthiocarbamic acid methyl ester in plasma (less than 24 hr); a significant effect was found 48 hr after pretreatment but not 72 hr after a single dose. No effect was observed when ethanol was given 15 min before diethylthiocarbamic acid methyl ester or disulfiram. These latter two observations are consistent with a function of diethylthiocarbamic acid methyl ester as a suicide inhibitor of aldehyde dehydrogenase. Since diethylthiocarbamic acid methyl ester has been reported to inhibit aldehyde dehydrogenase in vitro, even under anaerobic conditions, diethylthiocarbamic acid methyl ester may be the active metabolite of disulfiram.

PMID:2806369 Petersen EN; Eur J Pharmacol 166 (3): 419-25 (1989)


For more Metabolism/Metabolites (Complete) data for DISULFIRAM (7 total), please visit the HSDB record page.


5.7 Biological Half-Life

The elimination half-life of disulfiram in plasma is 7.3 hr. /From table/

Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 424


Following a 250 mg dose, the half-lives of disulfiram, diethyldithiocarbamate and carbon disulfide are 7.3 +/-1.5 hours, 15.5 +/-4.5 hours, and 8.9 +/-1.4 hours, respectively.

Goldfrank, L.R. (ed). Goldfrank's Toxicologic Emergencies. 7th Edition McGraw-Hill New York, New York 2002., p. 972


5.8 Mechanism of Action

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.


Acetaldehyde, produced as a result of oxidation of ethanol by alcohol dehydrogenase, ordinarily does not accumulate in the body, because it is further oxidized almost as soon as it is formed, primarily by aldehyde dehydrogenase. Following the administration of disulfiram, both cytosolic and mitochondrial forms of this enzyme are irreversibly inactivated to varying degrees, and the concentration of acetaldehyde rises. It is unlikely that disulfiram itself is responsible for the enzyme inactivation in vivo; several active metabolites of the drug, especially diethylthiomethylcarbamate, behave as suicide-substrate inhibitors of aldehyde dehydrogenase in vitro. These metabolites reach significant concentrations in plasma following the administration of disulfiram.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 441


Disulfiram (700 mg/kg, orally) increase brain levels of serotonin (i) and 5-hydroxyindoleacetic acid (5-hiaa) in rats. Ethanol (1 g/kg and 2x1.5 g/kg, ip) did not affect the serotonin level, but at the higher dose it increase the 5-hiaa level. When disulfiram was given in combination with ethanol, the brain level of serotonin was higher and the 5-hiaa level was lower, compared to the results with disulfiram alone. Thus, the biogenic aldehyde derived from serotonin may influence serotonin metab and the elimination of 5-hiaa from the brain.

PMID:6153360 Fukumori R et al; Eur J Pharmacol 61 (2): 199-202 (1980)


When disulfiram was given orally to rats at 40-400 mg/kg, the serum and, to a lesser extent, the liver cholesterol concentrations were increased and the liver microsome cholesterol 7alpha-hydroxylase activity decreased. The 7alpha-hydroxylase inhibition was completely reversed by dithiothreitol, indicating that disulfiram acted through its disulfide on 7alpha-hydroxylase. Increased serum cholesterol of alcoholics treated with disulfiram may be related to the inhibition of 7alpha-hydroxylase.

PMID:6477650 Anderson S, Bostroem H; Biochem Pharmacol 33 (18): 2930-2 (1984)


Human aldehyde dehydrogenase consists of two main isozymes with low and high Km for acetaldehyde. Studies regarding the inhibitory reaction of disulfiram and its metabolites were performed. Among the metabolites, diethylamine inhibited the low Km enzyme strongly. Vasomotor symptoms and high acetaldehyde concn in blood after ethanol intake in patients who are treated with disulfiram might be mainly due to a decrease in activity of the low Km enzyme caused by diethylamine which is produced in vivo as one of the metabolites from disulfiram, rather than to an inhibitory reaction of disulfiram only. Thus, alcohol sensitivity in Mongoloids and the disulfiram-ethanol reaction may have a common mechanism.

Harada S et al; Subst Alcohol Actions/Misuse 3 (1-2): 107-15 (1982)


For more Mechanism of Action (Complete) data for DISULFIRAM (19 total), please visit the HSDB record page.


API SUPPLIERS

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Polpharma

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Viatris

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Solara Active Pharma Sciences

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Corden Pharma Bergamo S.p.A

Italy

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25-Jan-2021
20-Aug-2024
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DOSAGE - TABLET;ORAL - 250MG

USFDA APPLICATION NUMBER - 88482

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USFDA APPLICATION NUMBER - 88483

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