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Chemistry

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Also known as: 148-79-8, Tiabendazole, Mintezol, 2-(4-thiazolyl)benzimidazole, Omnizole, Thiabenzole

Molecular Formula

C₁₀H₇N₃S

Molecular Weight

201.25 g/mol

InChI Key

WJCNZQLZVWNLKY-UHFFFAOYSA-N

FDA UNII

N1Q45E87DT

2-Substituted benzimidazole first introduced in 1962. It is active against a variety of nematodes and is the drug of choice for STRONGYLOIDIASIS. It has CENTRAL NERVOUS SYSTEM side effects and hepatototoxic potential. (From Smith and Reynard, Textbook of Pharmacology, 1992, p919)

Thiabendazole is an Anthelmintic.

1 2D Structure

Thiabendazole

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-(1H-benzimidazol-2-yl)-1,3-thiazole

2.1.2 InChI

InChI=1S/C10H7N3S/c1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9/h1-6H,(H,12,13)

2.1.3 InChI Key

WJCNZQLZVWNLKY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C2C(=C1)NC(=N2)C3=CSC=N3

2.2 Other Identifiers

2.2.1 UNII

N1Q45E87DT

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(4'-thiazolyl)benzimidazole

2. Mintesol

3. Mintezol

4. Omnizole

5. Thibendole

6. Tiabendazol

2.3.2 Depositor-Supplied Synonyms

1. 148-79-8

2. Tiabendazole

3. Mintezol

4. 2-(4-thiazolyl)benzimidazole

5. Omnizole

6. Thiabenzole

7. Equizole

8. Minzolum

9. Thiabendazol

10. Tiabendazol

11. Lombristop

12. Mintesol

13. Nemapan

14. Thibenzole

15. Bovizole

16. Thibenzol

17. Thiaben

18. Testo

19. Bioguard

20. Eprofil

21. Mertect

22. Mycozol

23. Pitrizet

24. Polival

25. Tebuzate

26. Tiabenda

27. Triasox

28. Mertec

29. Tobaz

30. Tbdz

31. Thibenzole Att

32. Apl-luster

33. Top Form Wormer

34. Cropasal

35. Sistesan

36. Thibendole

37. Ormogal

38. Storite

39. Thibenzole 200

40. Tecto Rph

41. 2-(4-thiazolyl)-1h-benzimidazole

42. Hokustar Hp

43. 2-(1,3-thiazol-4-yl)-1h-benzimidazole

44. 4-(1h-benzo[d]imidazol-2-yl)thiazole

45. Mertect 160

46. Tecto 10p

47. Tecto 40f

48. Tecto 60

49. 1h-benzimidazole, 2-(4-thiazolyl)-

50. Sanaizol 100

51. Chemviron Tk 100

52. Thiabendazolum

53. Thiabendole

54. Tiabendazolum

55. Biogard

56. Drawipas

57. Mintezole

58. Tecto

59. Mertect Lsp

60. E-z-ex

61. Equizole A

62. Tbz 60w

63. 4-(2-benzimidazolyl)thiazole

64. Captan T

65. Metasol Tk 100

66. 2-(thiazol-4-yl)benzimidazole

67. Helmindrax Octelmin

68. Thiabenzazole

69. Thiprazole

70. Tresaderm

71. Tubazole

72. 2-thiazole-4-ylbenzimidazole

73. Hymush

74. Nemacin

75. Mertect 340f

76. Metasol Tk-100

77. Syntol M100

78. Mk 360

79. Equivet Tz

80. Tecto B

81. Tibimix 20

82. Arbotect

83. 2-(1,3-thiazol-4-yl)benzimidazole

84. Thiabendazole [bsi:iso]

85. Tbz 6

86. Benzimidazole, 2-(4-thiazolyl)-

87. 2-(1,3-thiazol-4-yl)-1h-1,3-benzodiazole

88. Mk-360

89. 2-(4'-thiazolyl)benzimidazole

90. Mintezol (tn)

91. 4-(1h-benzimidazol-2-yl)-1,3-thiazole

92. Thiabendazole (usp)

93. Tiabendazole (jan/inn)

94. 4-(1h-benzimidazol-2-yl)thiazole

95. 1yvm

96. G 491

97. 5-(4-thiazolyl)benzimidazole

98. Tiabendazole [inn]

99. Rph

100. Nsc-90507

101. Chembl625

102. Nsc-525040

103. Mls000053094

104. N1q45e87dt

105. Chebi:45979

106. Nsc90507

107. Nsc525040

108. 2-(4-thiazolyl)-benzimidazole

109. Ncgc00016410-06

110. Ncgc00016410-13

111. Cas-148-79-8

112. E233

113. Smr000058170

114. 2-(1,3-thiazol-4-yl)-1h-benzoimidazole

115. Rtu Flowable Fungicide

116. Dsstox_cid_1337

117. 4-(1h-1,3-benzodiazol-2-yl)-1,3-thiazole

118. Dsstox_rid_76091

119. Dsstox_gsid_21337

120. Metasol Tk 10

121. Tiabendazolum [inn-latin]

122. Thiabendazole [usan:ban]

123. Tbz-6

124. 2-[4-thiazoly]benzimidazole

125. Caswell No. 849a

126. Tiabendazol [inn-spanish, French]

127. Wln: T56 Bm Dnj C-et5n Csj

128. Metasol Tk 25

129. Ccris 4510

130. Thiabendazole [iso]

131. Hsdb 2027

132. 2-thiazol-4-yl-1h-benzoimidazole

133. Sr-01000000188

134. Einecs 205-725-8

135. Nsc 90507

136. Epa Pesticide Chemical Code 060101

137. Nsc 525040

138. Thiabendazole [usan:usp]

139. Brn 0611403

140. Unii-n1q45e87dt

141. 2-(4-thiazoly)-benzimidazole

142. Ai3-50598

143. Tiabendazole, Inn

144. 2-(4-thiazolyl)-1h-benzoimidazole

145. Thiabendazole(usan)

146. Prestwick_813

147. Mfcd00005587

148. Thiabendazole, 98%

149. Spectrum_000039

150. Cpd000058170

151. Opera_id_336

152. Prestwick0_000524

153. Prestwick1_000524

154. Prestwick2_000524

155. Prestwick3_000524

156. Spectrum2_001331

157. Spectrum3_001407

158. Spectrum4_000354

159. Spectrum5_001009

160. Thiabendazole [mi]

161. Tiabendazole [jan]

162. Nciopen2_005709

163. Thiabendazole [hsdb]

164. Thiabendazole [inci]

165. Thiabendazole [usan]

166. Schembl19842

167. Bspbio_000507

168. Bspbio_003054

169. Kbiogr_000787

170. Kbioss_000399

171. Thiabendazole [vandf]

172. Tiabendazole [mart.]

173. 2(4-thiazolyl)-benzimidazole

174. Mls000069718

175. Bidd:er0372

176. Divk1c_000072

177. Spectrum1500570

178. Tiabendazole [who-dd]

179. Tiabendazole [who-ip]

180. Spbio_001481

181. Spbio_002428

182. Thiabendazole [usp-rs]

183. Bpbio1_000559

184. Gtpl7304

185. Dtxsid0021337

186. Thiabendazole, >=99%, Powder

187. Hms500d14

188. Kbio1_000072

189. Kbio2_000399

190. Kbio2_002967

191. Kbio2_005535

192. Kbio3_002274

193. Zinc73711

194. Ninds_000072

195. Hms1569j09

196. Hms1921e05

197. Hms2092m07

198. Hms2096j09

199. Hms2230f20

200. Hms3259e20

201. Hms3372e11

202. Hms3655e08

203. Hms3713j09

204. Pharmakon1600-01500570

205. Thiabendazole [green Book]

206. Tiabendazole [ep Impurity]

207. Thiabendazole [orange Book]

208. Tiabendazole [ep Monograph]

209. Albb-023635

210. Amy22461

211. Bcp19179

212. Hy-b0263

213. Tox21_110427

214. Tox21_202397

215. Tox21_300970

216. Bdbm50121347

217. Ccg-39633

218. Nsc757347

219. S1739

220. Stk394289

221. Thiabendazole [usp Monograph]

222. Akos000120940

223. Tox21_110427_1

224. Db00730

225. Nc00593

226. Nsc-757347

227. Sdccgmls-0002984.p003

228. Idi1_000072

229. Ncgc00016410-01

230. Ncgc00016410-02

231. Ncgc00016410-03

232. Ncgc00016410-04

233. Ncgc00016410-05

234. Ncgc00016410-07

235. Ncgc00016410-08

236. Ncgc00016410-09

237. Ncgc00016410-10

238. Ncgc00016410-11

239. Ncgc00016410-12

240. Ncgc00016410-14

241. Ncgc00016410-15

242. Ncgc00016410-18

243. Ncgc00016410-21

244. Ncgc00021671-04

245. Ncgc00021671-05

246. Ncgc00021671-06

247. Ncgc00021671-07

248. Ncgc00021671-08

249. Ncgc00021671-09

250. Ncgc00021671-10

251. Ncgc00254873-01

252. Ncgc00259946-01

253. Thiabendazole 100 Microg/ml In Methanol

254. Ac-10139

255. Ls-07459

256. Nci60_004280

257. Nci60_042006

258. Mls-0002984.p004

259. Sbi-0051531.p003

260. 2-(1,3-thiazole-4-yl)-1h-benzimidazole

261. Db-042952

262. Thiabendazole 10 Microg/ml In Acetonitrile

263. Ab00052107

264. Ft-0608694

265. Sw196947-3

266. T0830

267. Thiabendazole 100 Microg/ml In Acetonitrile

268. 2-(1,3-thiazol-4-yl)-1h-benzimidazole #

269. Thiabendazole 1000 Microg/ml In Acetonitrile

270. Thiabendazole, Ban, Bsi, Iso, Jmaf, Usan

271. 48t798

272. C07131

273. D00372

274. E70385

275. Ab00052107_17

276. Ab00052107_18

277. Thiabendazole, Pestanal(r), Analytical Standard

278. A808809

279. Q424986

280. Sr-01000000188-2

281. Sr-01000000188-4

282. Sr-01000000188-5

283. W-108097

284. Brd-k77695569-001-05-2

285. Brd-k77695569-001-16-9

286. Brd-k77695569-001-28-4

287. Thiabendazole, Certified Reference Material, Tracecert(r)

288. Thiabendazole, Bioreagent, Plant Cell Culture Tested, Powder

289. Tiabendazole, European Pharmacopoeia (ep) Reference Standard

290. Thiabendazole, United States Pharmacopeia (usp) Reference Standard

291. Thiabendazole, Pharmaceutical Secondary Standard; Certified Reference Material

292. 98002-42-7

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₇N₃S
Molecular Weight	201.25 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	201.03606841 g/mol
Monoisotopic Mass	201.03606841 g/mol
Topological Polar Surface Area	69.8 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	212
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

Antinematodal Agents

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

MEDICATION (VET): Thiabendazole is included in some otic preparations for treatment of yeast infections.

Kahn, C.M. (Ed.); The Merck Veterinary Manual 9th ed. Merck & Co. Whitehouse Station, NJ. 2005, p. 2102

MEDICATION (VET): The antifungal imidazoles also have some antibacterial action but are rarely used for this purpose. ... Thiabendazole is effective against Aspergillus and Penicillium spp , but its use has largely been replaced by the more effective imidazoles.

Kahn, C.M. (Ed.); The Merck Veterinary Manual 9th ed. Merck & Co. Whitehouse Station, NJ. 2005, p. 212

MEDICATION (VET): Imidazoles may have antibacterial, antifungal, antiprotozoal, and anthelmintic activity. ... The anthelmintic thiabendazole is also an imidazole with antifungal properties.

Kahn, C.M. (Ed.); The Merck Veterinary Manual 9th ed. Merck & Co. Whitehouse Station, NJ. 2005, p. 2101

For more Therapeutic Uses (Complete) data for THIABENDAZOLE (10 total), please visit the HSDB record page.

4.2 Drug Warning

The clinical utility of thiabendazole in adults is compromised by its toxicity. Side effects frequently encountered with therapeutic doses include anorexia, nausea, vomiting, and dizziness. Less frequently, diarrhea, fatigue, drowsiness, giddiness, or headache occur. Occasional fever, rashes, erythema multiforme, hallucinations, sensory disturbances, and Stevens-Johnson syndrome have been reported. Angioedema, shock, tinnitus, convulsions, and intrahepatic cholestasis are rare complications of therapy. Some patients excrete a metabolite that imparts an odor to the urine much like that occurring after ingestion of asparagus. Crystalluria without hematuria has been reported on occasion; it promptly subsides with discontinuation of therapy. Transient leukopenia has been noted in a few patients on thiabendazole therapy. There are no absolute contraindications to the use of thiabendazole. Because CNS side effects occur frequently, activities requiring mental alertness should be avoided during therapy. Thiabendazole has hepatotoxic potential and should be used with caution in patients with hepatic disease or decreased hepatic function.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 11th ed. New York, NY: McGraw-Hill, 2006., p. 1081

Hypersensitivity reactions consisting of pruritus, fever, facial flush, chills, conjunctival injection, rash (including perianal), angioedema, anaphylaxis, erythema multiforme (including Stevens-Johnson syndrome with some fatalities), and lymphadenopathy have occurred.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 64

Because adverse CNS effects of thiabendazole may occur quite frequently, patients should be warned that the drug may impair their ability to perform activities requiring mental alertness or physical coordination (e.g., operating machinery, driving a motor vehicle) and that such activities should be avoided.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 64

Thiabendazole should be used with caution in patients in whom vomiting might be dangerous and in patients with severe malnutrition or anemia. Ideally, supportive therapy is indicated for anemic, dehydrated, or malnourished patients prior to administration of the drug.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 64

For more Drug Warnings (Complete) data for THIABENDAZOLE (19 total), please visit the HSDB record page.

4.3 Drug Indication

For the treatment of strongyloidiasis (threadworm), cutaneous larva migrans (creeping eruption), visceral larva migrans, and trichinosis.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Thiabendazole is a fungicide and parasiticide. Thiabendazole is also a chelating agent, which means that it is used medicinally to bind metals in cases of metal poisoning, such as lead poisoning, mercury poisoning or antimony poisoning. Thiabendazole is vermicidal and/or vermifugal against Ascaris lumbricoides ("common roundworm"), Strongyloides stercoralis (threadworm), Necator americanus, Ancylostoma duodenale (hookworm), Trichuris trichiura (whipworm), Ancylostoma braziliense (dog and cat hookworm), Toxocara canis, Toxocara cati (ascarids), and Enterobius vermicularis (pinworm). Thiabendazole also suppresses egg and/or larval production and may inhibit the subsequent development of those eggs or larvae which are passed in the feces.

5.2 MeSH Pharmacological Classification

Anthelmintics

Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal. (See all compounds classified as Anthelmintics.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

THIABENDAZOLE

5.3.2 FDA UNII

N1Q45E87DT

5.3.3 Pharmacological Classes

Established Pharmacologic Class [EPC] - Anthelmintic

5.4 ATC Code

D - Dermatologicals

D01 - Antifungals for dermatological use

D01A - Antifungals for topical use

D01AC - Imidazole and triazole derivatives

D01AC06 - Tiabendazole

P - Antiparasitic products, insecticides and repellents

P02 - Anthelmintics

P02C - Antinematodal agents

P02CA - Benzimidazole derivatives

P02CA02 - Tiabendazole

5.5 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed and peak plasma concentration is reached within 1 to 2 hours after the oral administration of a suspension. Some systemic absorption may occur from topical preparations applied to the skin.

Route of Elimination

It is metabolized almost completely to the 5-hydroxy form which appears in the urine as glucuronide or sulfate conjugates.

Investigations in mice, rats and dogs using (14)C-labelled thiabendazole indicated that oral doses were rapidly absorbed from the gut and were distributed throughout the body (including the brain). Only 0.01% of the (14)C-thiabendazole given to rats was recovered as (14)C-carbon dioxide. Thiabendazole readily crossed the placental barrier to expose the fetuses.

European Medicine Agency (EMEA), The European Agency for the Evaluation of Medicinal Products, Veterinary Medicines Evaluation Unit, Committee for Veterinary Medicinal Products; Thiabendazole (148-79-8) EMEA/MRL/868/03, Summary Report (June 2004). Available from, as of June 10, 2009: https://www.ema.europa.eu/pdfs/vet/mrls/086803en.pdf

It becomes distributed throughout most of the body tissues, its highest concn in blood occurring at 4-7 hr after admin /in animals/.

Jones, L.M., et al. Veterinary Pharmacology & Therapeutics. 4th ed. Ames: Iowa State University Press, 1977., p. 1002

Absorption of thiabendazole by parasites is probably through the cuticle. Evidence from in vitro studies ... suggests that absorption ... is by means of passive diffusion of molecule through lipid barrier of nematode cuticle. This ... is not necessarily the case in vivo.

Jones, L.M., et al. Veterinary Pharmacology & Therapeutics. 4th ed. Ames: Iowa State University Press, 1977., p. 1003

Thiabendazole is rapidly absorbed and peak plasma concentrations occur within 1 to 2 hours. It is metabolized almost completely and appears in the urine as conjugates. In 48 hours, approximately 5% of the administered dose is recovered from feces and approximately 90% from urine. Most is excreted within the first 24 hours.

Novak, K.M. (ed.). Drug Facts and Comparisons 59th Edition 2005. Wolters Kluwer Health. St. Louis, Missouri 2005., p. 1830

For more Absorption, Distribution and Excretion (Complete) data for THIABENDAZOLE (10 total), please visit the HSDB record page.

5.6 Metabolism/Metabolites

Hepatic. Metabolized almost completely to the 5-hydroxy form which appears in the urine as glucuronide or sulfate conjugates.

In mice, rats and humans, the main pathway of metabolism of thiabendazole is an initial hydroxylation to form 5-hydroxythiabendazole, followed by conjugation to 5-hydroxythiabendazole glucuronide and 5-hydroxythiabendazole sulfate. In rats, 4-hydroxythiabendazole and 2-acetylbenzimidazole have been identified as minor metabolites or degradation products in urine.

... Treated beet leaves were exposed to sunlight for equiv of 14 8-hr days ... in addn to benzimidazole-2-carboxamide, benzimidazole and polar and polymer products were formed ... Thiabendazole was not metabolized by potatoes or cotton ...

Menzie, C.M. Metabolism of Pesticides, Update II. U.S. Department of the Interior, Fish Wildlife Service, Special Scientific Report - Wildlife No. 2l2. Washington, DC: U.S. Government Printing Office, 1978., p. 259

A single oral dose of thiabendazole was administered to four male human subjects. Feces and urine were collected. After an oral dose of 1.0 g of (14)C thiabendazole, plasma levels peaked at 1 to 2 hr and large amounts of radioactivity appeared rapidly in the urine. More than 40% of the label was excreted within 4 hr and 80% in 24 hr. Most of the dose appeared in urine as the glucuronide (35%) and sulfate (13%) of 5-hydroxy-TBZ. A small amount of unchanged TBZ and unconjugated 5-HO-TBZ were also present. The same compounds were observed with rats and dogs. It has also been reported that (14)C-labeling of the benzene ring in thiabendazole gave rise to some (14)CO2 by rats, indicating ring cleavage.

Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 507

Rat hepatic mixed function oxidase /activities in microsomal/ preparations hydroxylated thiabendazole. This activity seemed to be greatest in microsomal preparations > hepatocytes > slices.

Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 507

For more Metabolism/Metabolites (Complete) data for THIABENDAZOLE (9 total), please visit the HSDB record page.

Thiabendazole has known human metabolites that include 5-hydroxythiabendazole.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.7 Biological Half-Life

The half-life for thiabendazole in both normal and anephric patients is 1.2 hours (range 0.9 to 2 hours). The half-life for the 5-hydroxythiabendazole metabolite in both normal and anephric patients is 1.7 hours (range 1.4 to 2 hours).

5.8 Mechanism of Action

The precise mode of action of thiabendazole on the parasite is unknown, but it most likely inhibits the helminth-specific enzyme fumarate reductase.

Thiabendazole and other benzimidazole anthelmintics act by binding strongly to tubulin in the absorptive cells in the gut of parasitic worms. This interferes with the uptake of nutrients and the worms effectively starve to death. The host is less affected as the binding to mammalian tubulin is less strong and is reversible.

Although the exact mechanism of anthelmintic activity of thiabendazole has not been fully elucidated, the drug has been shown to inhibit the helminth-specific enzyme, fumarate reductase. In animals, thiabendazole has anti-inflammatory, antipyretic, and analgesic effects.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009), p. 65

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