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ACTIVE PHARMA INGREDIENTS

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ANALYTICAL

1 Analytical Methods

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1 Analytical Methods

Synopsis

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Chemistry

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Also known as: Tetramethylthiuram disulfide, 137-26-8, Thiuram, Rezifilm, Tmtd, Pomarsol

Molecular Formula

C₆H₁₂N₂S₄

Molecular Weight

240.4 g/mol

InChI Key

KUAZQDVKQLNFPE-UHFFFAOYSA-N

FDA UNII

0D771IS0FH

A dithiocarbamate chemical, used commercially in the rubber processing industry and as a fungicide. In vivo studies indicate that it inactivates the enzyme GLUTATHIONE REDUCTASE. It has mutagenic activity and may induce chromosomal aberrations.

Thiram is a Standardized Chemical Allergen. The physiologic effect of thiram is by means of Increased Histamine Release, and Cell-mediated Immunity.

1 2D Structure

Thiram

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

dimethylcarbamothioylsulfanyl N,N-dimethylcarbamodithioate

2.1.2 InChI

InChI=1S/C6H12N2S4/c1-7(2)5(9)11-12-6(10)8(3)4/h1-4H3

2.1.3 InChI Key

KUAZQDVKQLNFPE-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C)C(=S)SSC(=S)N(C)C

2.2 Other Identifiers

2.2.1 UNII

0D771IS0FH

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bacteriostat

2. Disulfide, Tetramethylthiuram

3. Disulfide, Tmt

4. Nobecutan

5. Sadoplon 75

6. Tetramethylthiuram Disulfide

7. Thiuram

8. Thiuram D

9. Tmt Disulfide

10. Tmtd

2.3.2 Depositor-Supplied Synonyms

1. Tetramethylthiuram Disulfide

2. 137-26-8

3. Thiuram

4. Rezifilm

5. Tmtd

6. Pomarsol

7. Thirame

8. Arasan

9. Fernasan

10. Nobecutan

11. Thioscabin

12. Thirasan

13. Aapirol

14. Tersan

15. Tetrathiuram Disulfide

16. Tetramethylthiuram

17. Falitiram

18. Formalsol

19. Hexathir

20. Kregasan

21. Mercuram

22. Normersan

23. Sadoplon

24. Spotrete

25. Tetrasipton

26. Thillate

27. Thiramad

28. Aatiram

29. Atiram

30. Fermide

31. Fernide

32. Hermal

33. Pomasol

34. Puralin

35. Thiosan

36. Thiotox

37. Thiulin

38. Thiulix

39. Heryl

40. Pomarsol Forte

41. Methyl Tuads

42. Polyram Ultra

43. Accelerator T

44. Methyl Thiram

45. Fernasan A

46. Tetramethylthiuram Disulphide

47. Nocceler Tt

48. Arasan-m

49. Bis(dimethylthiocarbamoyl) Disulfide

50. Thiram B

51. Arasan-sf

52. Cyuram Ds

53. Ekagom Tb

54. Hermat Tmt

55. Tetramethylenethiuram Disulfide

56. Accel Tmt

57. Accelerator Thiuram

58. Aceto Tetd

59. Radothiram

60. Royal Tmtd

61. Tetramethyl-thiram Disulfid

62. Fernacol

63. Sadoplon 75

64. Tetramethylthiuram Bisulfide

65. Tetrapom

66. Thioknock

67. Thirampa

68. Thiramum

69. Anles

70. Arasan-sf-x

71. Aules

72. Thimer

73. Panoram 75

74. Tetramethylthiouram Disulfide

75. Tetramethylthiurane Disulfide

76. Arasan 70

77. Arasan 75

78. Tersan 75

79. Thiram 75

80. Thiram 80

81. Spotrete-f

82. Tmtds

83. Arasan 70-s Red

84. Tetramethylthioperoxydicarbonic Diamide

85. Methylthiuram Disulfide

86. N,n-tetramethylthiuram Disulfide

87. Metiurac

88. Micropearls

89. Nomersan

90. Thianosan

91. Cunitex

92. Delsan

93. Thimar

94. Teramethylthiuram Disulfide

95. Tersantetramethyldiurane Sulfide

96. Pol-thiuram

97. Arasan 42-s

98. Tetramethylthiurum Disulfide

99. Disulfure De Tetramethylthiourame

100. Tetrathiuram Disulphide

101. Sranan-sf-x

102. Hy-vic

103. Sq 1489

104. Chipco Thiram 75

105. Bis(dimethyl-thiocarbamoyl)-disulfid

106. Orac Tmtd

107. Tetramethylthioramdisulfide

108. Tetramethyldiurane Sulphite

109. Thiotox (fungicide)

110. Disulfide, Bis(dimethylthiocarbamoyl)

111. Bis((dimethylamino)carbonothioyl) Disulfide

112. Fermide 850

113. Tetramethyl Thiuramdisulfide

114. Tetramethylthiocarbamoyldisulphide

115. Thiuramyl

116. Thylate

117. Methyl Thiuramdisulfide

118. Bis(dimethylthiocarbamyl) Disulfide

119. Tetramethyl Thiurane Disulfide

120. Bis(dimethyl Thiocarbamoyl)disulfide

121. Thirame [inn-french]

122. Thiramum [inn-latin]

123. Thiuram D

124. Disolfuro Di Tetrametiltiourame

125. Tetramethyl Thiurane Disulphide

126. Tetramethylenethiuram Disulphide

127. N,n'-(dithiodicarbonothioyl)bis(n-methylmethanamine)

128. Rcra Waste Number U244

129. Flo Pro T Seed Protectant

130. Tetramethylthiuram Bisulphide

131. Tetramethylthiuran Disulphide

132. Tetramethylthiurum Disulphide

133. Nsc-1771

134. Tetramethyl Thiuram Disulfide

135. Alpha,alpha'-dithiobis(dimethylthio)formamide

136. Thiotex

137. Thiurad

138. Tirampa

139. Tiuramyl

140. Trametan

141. Tridipam

142. Tripomol

143. Tyradin

144. Tuads

145. Tutan

146. Vulkacit Mtic

147. N,n,n',n'-tetramethylthiuram Disulfide

148. N,n-tetramethylthiuram Disulphide

149. Vulkacit Thiuram

150. Thioperoxydicarbonic Diamide, Tetramethyl-

151. Thiuram M

152. Vulkacit Th

153. Tetramethylthioramdisulfide [dutch]

154. Vulcafor Tmt

155. Vulcafor Tmtd

156. Bis((dimethylamino)carbonothioyl) Disulphide

157. Fmc 2070

158. Bis(dimethylthiocarbamoyl) Disulphide

159. Tetramethyl-thiram Disulfid [german]

160. Formamide, 1,1'-dithiobis(n,n-dimethylthio-

161. Dimethylcarbamothioylsulfanyl N,n-dimethylcarbamodithioate

162. Zaprawa Nasienna T

163. [me2nc(s)s]2

164. Vancida Tm-95

165. Disulfuro Di Tetrametiltiourame

166. Arasan 42s

167. Tuex

168. Disolfuro Di Tetrametiltiourame [italian]

169. Disulfuro Di Tetrametiltiourame [italian]

170. Disulfure De Tetramethylthiourame [french]

171. Nsc1771

172. Bis(dimethyl-thiocarbamoyl)-disulfid [german]

173. Vuagt-i-4

174. Nsc-49512

175. Thioperoxydicarbonic Diamide ([(h2n)c(s)]2s2), Tetramethyl-

176. Nsc-622696

177. [disulfanediylbis(carbonothioylnitrilo)]tetramethane

178. Thiuram M Rubber Accelerator

179. Mls000069752

180. Mls002702972

181. 0d771is0fh

182. Chebi:9495

183. Thiuram Disulfide, Tetramethyl-

184. Dtxsid5021332

185. Thiuram-m

186. Thioperoxydicarbonic Diamide (((h2n)c(s))2s2), Tetramethyl-

187. Nsc49512

188. Ccg-35460

189. Nsc-59637

190. Nsc622696

191. Tntd

192. Sq-1489

193. Ncgc00091563-01

194. Smr000059023

195. Thioperoxydicarbonic Diamide ((h2n)c(s))2s2, Tetramethyl-

196. [dithiobis(carbonothioylnitrilo)]tetramethane

197. Dsstox_cid_1332

198. Dsstox_rid_76087

199. .alpha.,.alpha.'-dithiobis(dimethylthio)formamide

200. Dsstox_gsid_21332

201. Caswell No. 856

202. Granuflo

203. Thiuramin

204. N,n',n'-tetramethylthiuram Disulfide

205. Thioperoxydicarbonic Diamide (((h2n)c(s))2s2), N,n,n',n'-tetramethyl-

206. Cas-137-26-8

207. Formamide,1'-dithiobis(n,n-dimethylthio-

208. Bis[(dimethylamino)carbonothioyl] Disulfide

209. Attack [antifungal]

210. Thiram [iso]

211. Nsc59637

212. Ccris 1282

213. Hsdb 863

214. Ent 987

215. Wln: 1n1 & Yus & Ssyus & N1 & 1

216. Nsc 1771

217. Einecs 205-286-2

218. Nsc 49512

219. Nsc 59637

220. Rcra Waste No. U244

221. Epa Pesticide Chemical Code 079801

222. Nsc 622696

223. Brn 1725821

224. Tiramo

225. Unii-0d771is0fh

226. Basultra

227. Betoxin

228. Tiradin

229. Accelerant T

230. Ai3-00987

231. Arasan M

232. Vulkazam S

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

234. Vanguard Gf

235. Vancide Tm

236. Akrochem Tmtd

237. Perkacit Tmtd

238. Vulkacit Dtmt

239. Robac Tmt

240. Thiram (tmtd)

241. Rezifilm (tn)

242. Arasan 50 Red

243. Spotrete Wp 75

244. Mfcd00008325

245. Vancide Tm-95

246. Naftocit Thiuram 16

247. Spectrum_001687

248. Thiram (usan/inn)

249. Agrichem Flowable Thiram

250. Thiram [hsdb]

251. Thiram [iarc]

252. Thiram [inci]

253. Thiram [usan]

254. Thiram [inn]

255. Spectrum2_001554

256. Spectrum3_001592

257. Spectrum4_000860

258. Spectrum5_001653

259. Thiram [who-dd]

260. Thiram [mi]

261. Thiram [mart.]

262. Bmse000928

263. Ec 205-286-2

264. Ncimech_000272

265. Cid_5455

266. Nciopen2_007854

267. Schembl21144

268. Bspbio_003184

269. Kbiogr_001499

270. Kbioss_002167

271. 4-04-00-00242 (beilstein Handbook Reference)

272. Bidd:er0359

273. Divk1c_000741

274. Spectrum1503322

275. Spbio_001428

276. Chembl120563

277. Thiram [usan:inn:bsi:iso]

278. Bdbm43362

279. Hms502f03

280. Kbio1_000741

281. Kbio2_002167

282. Kbio2_004735

283. Kbio2_007303

284. Kbio3_002684

285. Kuazqdvkqlnfpe-uhfffaoysa-

286. Ent-987

287. Ninds_000741

288. Hms1922a12

289. Hms2093e03

290. Hms2234b08

291. Hms3374c05

292. Pharmakon1600-01503322

293. Tetramethylthiuram Disulfide, 97%

294. Thiram 100 Microg/ml In Ethanol

295. Zinc1532176

296. Tox21_111150

297. Tox21_201569

298. Tox21_301102

299. Nsc758454

300. S2431

301. Stl264104

302. (dimethylamino){[(dimethylamino)thioxomethyl]disulfanyl}methane-1-thione

303. Akos000120200

304. Bis (dimethyl Thiocarbamoyl) Disulfide

305. Bis(dimethylaminothiocarbonyl)disulfide

306. Tox21_111150_1

307. Bis(dimethylaminothiocarbonyl) Disulfide

308. Db13245

309. Ks-5354

310. Nsc-758454

311. Idi1_000741

312. Qtl1_000082

313. Ncgc00091563-02

314. Ncgc00091563-03

315. Ncgc00091563-04

316. Ncgc00091563-05

317. Ncgc00091563-06

318. Ncgc00091563-07

319. Ncgc00091563-08

320. Ncgc00091563-09

321. Ncgc00091563-10

322. Ncgc00091563-12

323. Ncgc00255002-01

324. Ncgc00259118-01

325. Nci60_001477

326. Nci60_006736

327. Sbi-0051813.p002

328. Thiram, Pestanal(r), Analytical Standard

329. Db-042384

330. B0486

331. Cs-0012858

332. Ft-0631799

333. 37t268

334. D06114

335. D97716

336. Ab00052345_10

337. Q416572

338. Sr-01000736911

339. J-006992

340. J-524968

341. Sr-01000736911-2

342. Thiram, Certified Reference Material, Tracecert(r)

343. Brd-k29254801-001-06-3

344. F0001-0468

345. Tetramethylthioperoxydicarbonic Acid [(h2n)c(s)]2s2

346. N,n-dimethyl[(dimethylcarbamothioyl)-disulfanyl]carbothioamide

347. N,n-dimethyl[(dimethylcarbamothioyl)disulfanyl]carbothioamide

348. 1-(dimethylthiocarbamoyldisulfanyl)-n,n-dimethyl-methanethioamide

349. N,n-dimethylcarbamodithioic Acid (dimethylthiocarbamoylthio) Ester

350. N(1),n(1),n(3),n(3)-tetramethyl-2-dithioperoxy-1,3-dithiodicarbonic Diamide

351. N,n-dimethylcarbamodithioic Acid [[dimethylamino(sulfanylidene)methyl]thio] Ester

352. Tetramethylthioperoxydicarbonic Diamide ((((ch(sub 3))(sub 2)n)c(s))(sub 2)s(sub 2))

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₆H₁₂N₂S₄
Molecular Weight	240.4 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	239.98833309 g/mol
Monoisotopic Mass	239.98833309 g/mol
Topological Polar Surface Area	121 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	158
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Anti-Infective Agents, Local; Antifungal Agents; Carcinogens; Enzyme Inhibitors; Fungicides, Industrial; Mutagens

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

Has wide spectrum of antibacterial activity ... also effective against several dermatophytes. Serum does not appear to suppress its activity. ... marketed only as component of plastic film that is sprayed onto dry surgical wounds for purpose of preventing post operative infections. ... film containing 0.5% thiram.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1104

Antifungal (topical)

Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 1476

Used in antiseptic sprays.

Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, DC: Association of American Railroads, Bureau of Explosives, 1994., p. 1051

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Mutagens

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. (See all compounds classified as Mutagens.)

Fungicides, Industrial

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. (See all compounds classified as Fungicides, Industrial.)

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

THIRAM

5.2.2 FDA UNII

0D771IS0FH

5.2.3 Pharmacological Classes

Chemical Structure [CS] - Allergens

5.3 ATC Code

P - Antiparasitic products, insecticides and repellents

P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents

P03A - Ectoparasiticides, incl. scabicides

P03AA - Sulfur containing products

P03AA05 - Thiram

5.4 Absorption, Distribution and Excretion

Tetramethylthiuramdisulfide appears to be readily absorbed through the intestinal tract and the lungs and is quickly and widely distributed throughout the body.

O'Donoghue, J.L. (ed.). Neurotoxicity of Industrial and Commercial Chemicals. Volume II. Boca Raton, FL: CRC Press, Inc., 1985., p. 48

In 2 days following its ingestion, bis(dimethylthiocarbamoyl) disulfide (TMTD) is found in the liver and spleen together with its metabolites: amine salt dimethyldithiocarbamic acid (DDCA) and tetramethylthiourea, and in the lungs, carbon disulfide and the amine salt of DDCA. TMTD is known to form N-nitrosodimethylamine by reaction with nitrite in mildly acid solution. TMTD and the amine salt of DDCA are excreted from the body in the urine and feces, and as carbon disulfide via the lungs.

Sheftel, V.O.; Indirect Food Additives and Polymers. Migration and Toxicology. Lewis Publishers, Boca Raton, FL. 2000., p. 551

After absorption (respiratory, dermal, gastrointestinal), thiram is distributed in all organs and is mainly excreted unchanged in urine and feces. Some metabolism exists; carbon dioxide is exhaled and dithiocarbamate is excreted in urine.

American Conference of Governmental Industrial Hygienists. Documentation of Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices for 2001. Cincinnati, OH. 2001., p. 3

5.5 Metabolism/Metabolites

In studies with ruminant animals fed corn treated with thiram, rumen microorganisms degraded thiram to carbon disulfide and probably hydrogen sulfide and dimethylamine. ... some unchanged thiram was also observed in feces /and/ urine.

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. 310

Pesticides and nitrites in food may be a hazard to man, since many pesticides are secondary or tertiary amines, which form nitroso compounds in the presence of nitrite under conditions resembling those in the human stomach. Compounds were incubated for 4 hours at 37 C in the presence of excess nitrite at pH 3. Thiram converted to the carcinogen dimethylnitrosamine at a yield of 9%.

PMID:7518 Egert G, Greim H; Food Cosmet Toxicol 14 (3): 193-5 (1976)

The major metabolite in plants is ethylene thiourea, followed by ethylene thiuram monosulfide and presumably ethylene thiuram disulfide and sulfur.

Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. 2nd ed. Lechworth, Herts, England: The Royal Society of Chemistry, 1987., p. A399/Aug 87

The hepatotoxic effects of thiram metabolism to carbon disulfide were investigated in rats. Male Sprague-Dawley rats were administered 15, 30 or 60 mg/kg thiram ip. Activities of serum glutamic oxaloacetic transaminase and sorbitol dehydrogenase were measured in the blood to assess the extent of liver injury. Detectable amounts of carbon disulfide appeared after 1.5 to 2 hr of treatment; 5 hr were required for complete recovery of carbon disulfide produced from 60 mg/kg thiram. A 2 fold increase in the dose of thiram from 15 to 30 mg/kg resulted in a 10 fold increase in the amount of carbon disulfide in expired air. Increasing the thiram dose 4 times to 60 mg/kg resulted in a 40 fold increase in carbon disulfide production over that from a 15 mg/kg thiram dose. The microsomal inhibitor SKF-525A inhibited the formation of carbon disulfide from thiram; phenobarbital treatment increased the formation of carbon disulfide. Thiram caused a significant loss of cytochrome P450 and benzphetamine-N-demethylase activity at 24 hr following treatment. Five hours after 60 mg/kg thiram treatment, there was an increase in sorbitol dehydrogenase activity 47%; serum glutamic oxaloacetic transaminase activity increased by 41 and 40% during 5 and 24 hr, respectively. /It was/ concluded that carbon disulfide is an in vivo metabolite of thiram and may be responsible for hepatotoxicity.

PMID:3953292 Dalvi RR, Deoras DP; Acta Pharmacologica et Toxicologica 58 (1): 38-42 (1986)

For more Metabolism/Metabolites (Complete) data for THIRAM (6 total), please visit the HSDB record page.

5.6 Mechanism of Action

Inhibition of hepatic dehydrogenases results in an acetaldehyde reaction on exposure to ethanol. Other effects may result from the known reactions of dithiocarbamates with metals, sulfhydryl-containing enzymes, or metabolism to reactive metabolites including carbon disulfide.

O'Donoghue, J.L. (ed.). Neurotoxicity of Industrial and Commercial Chemicals. Volume II. Boca Raton, FL: CRC Press, Inc., 1985., p. 48

...Ingestion of the fungicide thiram (125 mg/kg)... /has/ been reported to evoke ovarian atrophy and cessation of egg laying in hens, presumably through inhibition of dopamine beta-hydroxylase.

Shore R.F., Rattner BA. Ecotoxicology of Wild Mammals. Ecological & Environmental Toxicology Series 2001. John Wiley & Sons, New York, N.Y. 2001, p. 12

... /It was/ previously demonstrated that Disulfiram impairs the permeability of inner mitochondrial membrane (IMM). In this report, the effect of Disulfiram and its structural analogue thiram (Th) on mitochondrial functions was studied in detail. /It was/ found that mitochondria metabolize thiram disulfide compounds (TDs) in a NAD(P)H- and GSH-dependent manner. At the concentration above characteristic threshold, TDs induced irreversible oxidation of NAD(P)H and glutathione (GSH) pools, collapse of transmembrane potential, and inhibition of oxidative phosphorylation. The presence of Ca(2+) and exhaustion of mitochondrial glutathione (GSH+GSSG) decreased the threshold concentration of TDs. ... TDs induced the mitochondrial permeability transition (MPT).

PMID:11714485 Balakirev MY, Zimmer G; Chem Biol Interact 138 (3): 299-311 (2001)

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