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Chemistry

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Also known as: Metrifonate, Chlorophos, 52-68-6, Metriphonate, Trichlorphon, Methyl chlorophos
Molecular Formula
C4H8Cl3O4P
Molecular Weight
257.43  g/mol
InChI Key
NFACJZMKEDPNKN-UHFFFAOYSA-N
FDA UNII
37VCQ9C0OG

Trichlorfon
An organochlorophosphate cholinesterase inhibitor that is used as an insecticide for the control of flies and roaches. It is also used in anthelmintic compositions for animals. (From Merck, 11th ed)
1 2D Structure

Trichlorfon

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2,2,2-trichloro-1-dimethoxyphosphorylethanol
2.1.2 InChI
InChI=1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3
2.1.3 InChI Key
NFACJZMKEDPNKN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COP(=O)(C(C(Cl)(Cl)Cl)O)OC
2.2 Other Identifiers
2.2.1 UNII
37VCQ9C0OG
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bilarcil

2. Chlorofos

3. Chlorophos

4. Dipterex

5. Dylox

6. Foschlor

7. Metrifonate

8. Metriphonate

9. Neguvon

10. Ricifon

11. Trichlorphon

2.3.2 Depositor-Supplied Synonyms

1. Metrifonate

2. Chlorophos

3. 52-68-6

4. Metriphonate

5. Trichlorphon

6. Methyl Chlorophos

7. Trichlorofon

8. Bilarcil

9. Chlorofos

10. Dylox

11. Chloroftalm

12. Chloroxyphos

13. Dipterex

14. Foschlor

15. Neguvon

16. Ricifon

17. Detf

18. Agroforotox

19. Chlorophthalm

20. Fliegenteller

21. Hypodermacid

22. Khloroftalm

23. Metrifonatum

24. Polfoschlor

25. Trichlorophon

26. Bovinox

27. Cekufon

28. Diptevur

29. Ditrifon

30. Forotox

31. Masoten

32. Mazoten

33. Phoschlor

34. Ritsifon

35. Sotipox

36. Volfartol

37. Votexit

38. Wotexit

39. Anthon

40. Briten

41. Briton

42. Combot

43. Danex

44. Dyrex

45. Dyvon

46. Loisol

47. Proxol

48. Soldep

49. Trinex

50. Tugon

51. (+-)-trichlorfon

52. Trichlorphon Fn

53. Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate

54. Equino-aid

55. Foschlor R

56. Bayer L 1359

57. Chlorophosciclosom

58. Flibol E

59. Dep (pesticide)

60. Dipterex 50

61. Trichloorfon

62. Clorofos

63. Denkaphon

64. Dioxaphos

65. Foschlorem

66. Chlorak

67. Dimetox

68. Phoschlor R50

69. Dipterex Wp 80

70. Foschlor R-50

71. Metrifonato

72. Trichlorophone

73. Trichlorfon [usan]

74. Wec 50

75. Bay-a 9826

76. Bayer L 13/59

77. Nci-c54831

78. Bay 15922

79. Metifonate

80. Triclorfon

81. Dipterax

82. Neguron

83. Ent 19,763

84. Oms 800

85. Bayer-l-1359

86. 1-hydroxy-2,2,2-trichloroethylphosphonic Acid Dimethyl Ester

87. Bay-l 1359

88. (+)-trichlorfon

89. (-)-trichlorfon

90. Phosphonic Acid, (2,2,2-trichloro-1-hydroxyethyl)-, Dimethyl Ester

91. Metrifonate [inn]

92. Dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate

93. Metrifonate, (+)-

94. Metrifonate, (-)-

95. Nsc-8923

96. Dbf2dg4g2k

97. 1mvy4ku98f

98. 37vcq9c0og

99. Dimethyl(2,2,2-trichloro-1-hydroxyethyl)phosphonate

100. O,o-dimethyl-1-oxy-2,2,2-trichloroethyl Phosphonate

101. Dimethyl (1-hydroxy-2,2,2-trichloroethyl)phosphonate

102. Mls000069726

103. Chebi:6908

104. Chembl167150

105. O,o-dimethyl (1-hydroxy-2,2,2-trichloroethyl)phosphonate

106. O,o-dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate

107. Wec-50

108. 2,2,2-trichloro-1-dimethoxyphosphorylethanol

109. (2,2,2-trichloro-1-hydroxyethyl)phosphonic Acid Dimethyl Ester

110. O,o-dimethyl-(1-hydroxy-2,2,2-trichloraethyl)phosphosaeure Ester

111. Phosphonic Acid, (1-hydroxy-2,2,2-trichloroethyl)-, Dimethyl Ester

112. Trichlorfon (usan)

113. Ent-19,763

114. O,o-dimethyl-(1-hydroxy-2,2,2-trichlorathyl)-phosphat

115. O,o-dimetil-(2,2,2-tricloro-1-idrossi-etil)-fosfonato

116. 1-hydroxy-2,2,2-trichloro-ethyle Phosphonate De Dimethyle

117. O,o-dimethyl-(2,2,2-trichlor-1-hydroxy-aethyl)phosphonat

118. Ncgc00018237-03

119. Metriphonatum

120. Britten

121. Chlorfos

122. Chlorphos

123. Ciclosom

124. Depthon

125. Leivasom

126. O,o-dimethyl-(2,2,2-trichloor-1-hydroxy-ethyl)-fosfonaat

127. Smr000058176

128. Dimethyl (trichlorohydroxyethyl)phosphonate

129. Combot Equine

130. Dicontal Fort

131. Tugon Fly Bait

132. Dsstox_cid_1389

133. Dipterex Sl

134. Ditriphon 50

135. Dsstox_rid_76131

136. Tugon Stable Spray

137. Dsstox_gsid_21389

138. Foschlor 25

139. 26373-97-7

140. Aerol 1

141. Foschlorem [polish]

142. Trichlorphon [iso]

143. Satox 20wsc

144. Trichloorfon [dutch]

145. Trichlorfon [german]

146. Aerol 1 (pesticide)

147. Caswell No. 385

148. Vermicide Bayer 2349

149. Trichlorfon [bsi:iso]

150. Bayer 15922

151. Metrifonatum [inn-latin]

152. Phosphonic Acid, (2,2,2-trichloro-1-hydroxyethyl)-, Dimethyl Ester, (+)-

153. Phosphonic Acid, (2,2,2-trichloro-1-hydroxyethyl)-, Dimethyl Ester, (-)-

154. Phosphonic Acid, P-(2,2,2-trichloro-1-hydroxyethyl)-, Dimethyl Ester, (+)-

155. Phosphonic Acid, P-(2,2,2-trichloro-1-hydroxyethyl)-, Dimethyl Ester, (-)-

156. Foschlor R-50 (van)

157. Metrifonato [inn-spanish]

158. 56042-26-3

159. 56042-27-4

160. Ccris 1289

161. Hsdb 881

162. Clorofos [russian]

163. Nsc 8923

164. Einecs 200-149-3

165. Unii-dbf2dg4g2k

166. Epa Pesticide Chemical Code 057901

167. Dimethyltrichlorohydroxyethyl Phosphonate

168. Brn 1709434

169. Ertefon

170. Memobay

171. Zeltivar

172. Onefon

173. Promem

174. Ai3-19763

175. Cas-52-68-6

176. Phoschlor R.50

177. Prestwick_599

178. Foschlor R 50

179. Trichlorphon Solution

180. Dimethyl 1-hydroxy-2,2,2-trichloroethyl Phosphonate

181. O,o-dimethyl (1-oxy-2,2,2-trichloroethyl)phosphonate

182. O,o-dimethyl-1-hydroxy-2,2,2-trichloroethylphosphonate

183. Totalene (salt/mix)

184. (+/-)-trichlorfon

185. Tri Chlorfon

186. Dimethoxy-2,2,2-trichloro-1-hydroxy-ethyl Phosphine Oxide

187. Dimethoxy-2,2,2-trichloro-1-hydroxy-ethyl-phosphine Oxide

188. O,o-dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosponate

189. Starbld0043468

190. Opera_id_345

191. Metrifonate (usp/inn)

192. Trichlorfon [mi]

193. (2,2,2-trichloro-1-hydroxyethyl)-phosphonic Acid Dimethyl Ester

194. 1-hydroxy-2,2,2-trichloro-ethyle Phosphonate De Dimethyle [french]

195. O,o Dimetil 2,2,2-trichloro 1 Hidroxietil Fosfonato (portugese)

196. O,o-dimethyl-(1-hydroxy-2,2,2-trichlorathyl)-phosphat [german]

197. O,o-dimethyl-(2,2,2-trichloor-1-hydroxy-ethyl)-fosfonaat [dutch]

198. O,o-dimethyl-(2,2,2-trichlor-1-hydroxy-aethyl)phosphonat [german]

199. O,o-dimetil-(2,2,2-tricloro-1-idrossi-etil)-fosfonato [italian]

200. Prestwick0_000051

201. Prestwick1_000051

202. Prestwick2_000051

203. Prestwick3_000051

204. Trichlorfon [iso]

205. (.+/-.)-trichlorfon

206. Trichlorfon [hsdb]

207. Trichlorfon [iarc]

208. Unii-1mvy4ku98f

209. Unii-37vcq9c0og

210. O,o-dimethyl-(1-hydroxy-2,2,2-trichloraethyl)phosphonsaeure Ester [german]

211. Cid_5853

212. Bay-a-9826

213. Metrifonate [mart.]

214. Schembl15972

215. Bspbio_000201

216. Metrifonate [who-dd]

217. Metrifonate [who-ip]

218. Trichlorfon [usp-rs]

219. Spbio_002122

220. Wln: Gxggyqpo&o1&o1

221. Bpbio1_000223

222. O,2,2-trichlorathyl)-phosphat

223. O,2,2-trichloroethyl)phosphate

224. Dtxsid0021389

225. Trichlorfon [green Book]

226. Metrifonate [ep Impurity]

227. Nsc8923

228. Hms1568k03

229. Hms2095k03

230. Metrifonate [usp Impurity]

231. Pharmakon1600-01505765

232. Metrifonate [usp Monograph]

233. Hy-b1220

234. Metrifonatum [who-ip Latin]

235. Tox21_110843

236. Tox21_201607

237. Tox21_300860

238. Bdbm50286920

239. Nsc759241

240. O,o-dimethyl-(1-hydroxy-2,2,2-trichloraethyl)phosphonsaeure Ester

241. Akos001499170

242. Tox21_110843_1

243. Ccg-213546

244. Cs-4845

245. Db11473

246. Nsc-759241

247. Trichlorfon 100 Microg/ml In Methanol

248. O,2,2-trichlorohydroxyethyl)phosphonate

249. Ncgc00018237-02

250. Ncgc00018237-04

251. Ncgc00018237-06

252. Ncgc00018237-07

253. Ncgc00018237-09

254. Ncgc00089822-02

255. Ncgc00089822-03

256. Ncgc00254763-01

257. Ncgc00259156-01

258. O,2,2-trichloraethyl)phosphosaeure Ester

259. O,2,2-tricloro-1-idrossi-etil)-fosfonato

260. Sbi-0206912.p001

261. Trichlorfon 100 Microg/ml In Acetonitrile

262. 0,2,2-trichloro-1-hydroxyethyl)phosphonate

263. O,2,2-trichloro-1-hydroxyethyl)phosphonate

264. O,2,2-trichloor-1-hydroxy-ethyl)-fosfonaat

265. O,2,2-trichlor-1-hydroxy-aethyl)phosphonat

266. C07971

267. D00805

268. F21293

269. Trichlorfon, Pestanal(r), Analytical Standard

270. Q422991

271. Sr-01000000181

272. Dimethyl (1-hydroxy-2,2-trichloroethyl)phosphonate

273. Dimethyl (2,2-trichloro-1-hydroxyethyl)phosphonate

274. Dimethyl 1-hydroxy-2,2,2-trichloroethylphosphonate

275. Q-201859

276. Sr-01000000181-2

277. (2,2,2-trichloro-1-hydroxyethyl) Dimethylphosphonate

278. [(2,2-trichloro-1-hydroxyethyl) Dimethylphosphonate]

279. O,o-dimethyl (2,2,2-trichlorohydroxyethyl)phosphonate

280. Phosphonic Acid,2,2-trichloroethyl)-, Dimethyl Ester

281. Trichloro-alpha-hydroxyethyl Phosphonic Dimethyl Ester

282. 1-hydroxy-2,2-trichloro-ethyle Phosphonate De Dimethyle

283. Dimethoxy-(2,2-trichloro-1-hydroxyethyl)phosphine Oxide

284. O,o-dimethyl (1-hydroxy-2,2,2-trichloroethyl)phosphate

285. (2,2-trichloro-1-hydroxy)phosphonic Acid, Dimethyl Ester

286. (2,2-trichloro-1-hydroxyethyl)phosphonate, Dimethyl Ester

287. Dimethoxy-(2,2,2-trichloro-1-hydroxyethyl)phosphine Oxide

288. Metrifonate, European Pharmacopoeia (ep) Reference Standard

289. (1-hydroxy-2,2-trichloroethyl)phosphonic Acid, Dimethyl Ester

290. (2,2,2-trichloro-1-hydroxyethyl)phosphonate, Dimethyl Ester

291. (2,2-trichloro-1-hydroxyethyl)phosphonic Acid Dimethyl Ester

292. 1-hydroxy-2,2,2-trichloroethylphosphonate-o,o-dimethyl Ester

293. Phosphonic Acid,2,2-trichloro-1-hydroxyethyl)-, Dimethyl Ester

294. (1-hydroxy-2,2,2-trichloroethyl)phosphonic Acid, Dimethyl Ester

295. 2,2-trichloro-1-hydroxyethyl)phosphonic Acid, Dimethyl Ester

296. Dimethyl (p)-(2,2,2-trichloro-1-hydroxyethyl)phosphonate

297. Dimethyl (rs)-2,2,2-trichloro-1-hydroxyethylphosphonate

298. Trichlorfon, United States Pharmacopeia (usp) Reference Standard

299. Phosphonic Acid, P-(2,2,2-trichloro-1-hydroxyethyl)-, Dimethyl Ester

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 257.43 g/mol
Molecular Formula C4H8Cl3O4P
XLogP30.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Exact Mass255.922579 g/mol
Monoisotopic Mass255.922579 g/mol
Topological Polar Surface Area55.8 Ų
Heavy Atom Count12
Formal Charge0
Complexity183
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Anthelmintics; Cholinesterase Inhibitors; Insecticides.

National Library of Medicine's Medical Subject Headings. Trichlorfon. Online file (MeSH, 2017). Available from, as of May 24, 2017: https://www.nlm.nih.gov/mesh/2017/mesh_browser/MBrowser.html


Trichlorfon has been used to treat helminthiasis, including ankylostomiasis, ascariasis, trichuriasis, and creeping eruption in human. The expected pharmacological effects of the drug did appear as side effects but these effects were no more severe or frequent than those of other anthelminthics. Trichlorfon is effective for treating even Schistosoma hematobium infection.

Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 1, 2nd ed. 2001. Academic Press, San Diego, California., p. 56


/EXPL THER/ Metrifonate (trichlorfon) is an inhibitor of acetylcholinesterase (AChE). It was used as an Alzheimer's disease (AD) drug; however, the application was withdrawn due to adverse effects. Implication of metrifonate for the antioxidant status and regulation of apoptotic processes was evaluated in the present study. Wistar rats (six per group) were exposed subcutaneously to either 60 or 120 mg/kg of body weight of metrifonate and compared with the controls treated with saline only. Cerebral cortex and liver tissues were collected from animals 40 min after exposure. Activities of AChE, glutathione reductase, glutathione-S-transferase, caspase 3, total protein level, thiobarbituric acid reactive substances, reduced glutathione level and ferric reducing antioxidant power (FRAP) were assayed in the tissue samples. Metrifonate had only lower impact on oxidative stress in the liver. Cerebral cortex tissues had decreased AChE and increased caspase 3 activities as well as the FRAP level. Owing to the novel findings, suitability of metrifonate for AD therapy is discussed.

PMID:21943232 Pohanka M et al; Toxicol Mech Methods 21 (8): 585-90 (2011)


Metrifonate is an excellent drug for the treatment of urinary schistosomiasis in areas with Schistosoma haematobium monoinfection. Toxicity apparently is negligible. Side effects due to the inhibition of acetylcholinesterase are usually scarce, light and transient in nature. At the recommended dosage of 3 time 10 mg/kg the chemotherapeutic potential of metrifonate to cure can be expected to range between 60 and 90%. Each dose of metrifonate reduces egg excretion by almost 90%. Treatment with metrifonate clearly reverses lower and upper renal tract pathology. When appropriately timed with regards to local transmission dynamics the minimal requirement to achieve 99% reduction of egg excretion may be as low as three or four doses spaced over a period of two years.

Feldmeier H, Doehring E; Acta Trop (Basel) 44 (3): 357-68 (1987)


For more Therapeutic Uses (Complete) data for Trichlorfon (13 total), please visit the HSDB record page.


4.2 Drug Warning

/Metrifonate/ treated individuals should be free from recent exposure to insecticides that might add to the anticholinesterase effect. They also should not receive depolarizing neuromuscular blocking agents for at least 48 hr after treatment.

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. 1133


VET: Do not use in conjunction with or within few days of (before or after) any other cholinesterase inhibitors; avoid use with phenothiazine, phenothiazine tranquilizers, arsenicals, purgatives or drugs producing purgation as side effect. Possibility of adverse reactions in heartworm infested dogs ... suggested. Do not contaminate feed or water except as in product use directions. Apply to cattle as directed only after milking. Skin sensitivity ... reported ... on pets wearing "flea collars." Avoid use in very young, debilitated, and constipated animals, or those with cirrhotic livers or acute infectious diseases.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 615


A 60% depression in red /blood/ cell /(cholinesterase)/ ChE and 80% depression in plasma ChE were accompanied by only minor side effects (nausea, vomiting, and/or diarrhea) ... .

WHO; Environ Health Criteria 132: Trichlorfon p. 74 (1992)


In ... /a/ study designed to evaluate the safety and tolerability of relatively high loading doses followed by lower maintenance doses and to determine the maximum tolerated dose of trichlorfon, groups of probable Alzheimer's disease patients were administered either 2.5 mg/kg/day for 14 days followed by 4.0 mg/kg/day for 3 days, then 2.0 mg/kg/day for 14 days or 2.5 mg/kg/day for 14 days followed by 1.5 mg/kg/day for 35 days. RBC acetylcholinesterase inhibition occurred in all groups. Moderate to severe cholinergic effects (muscle cramps, abdominal discomfort, headache, muscle weakness, generalized moderate to severe muscle cramps, weakness, inability to resume daily activities, and coordination difficulties) occurred in 6 of 8 patients given the higher doses (4.0 mg/kg/day for 3 days and 2.0 mg/kg/day for 14 days); mild to moderate cholinergic effects (gastrointestinal disturbances, muscle cramps, and light-headedness/dizziness) occurred among patients given the lower maintenance dose (1.5 mg/kg/day). /Former use/

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 934


For more Drug Warnings (Complete) data for Trichlorfon (6 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 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.)


Cholinesterase Inhibitors

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)


Insecticides

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)


5.2 ATC Code

P - Antiparasitic products, insecticides and repellents

P02 - Anthelmintics

P02B - Antitrematodals

P02BB - Organophosphorous compounds

P02BB01 - Metrifonate


5.3 Absorption, Distribution and Excretion

Absorbed by skin.

Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1364


Trichlorfon ... is not readily absorbed by cotton leaves.

White-Stevens, R. (ed.). Pesticides in the Environment: Volume 1, Part 1, Part 2. New York: Marcel Dekker, Inc., 1971., p. 176


In cow, (32)P-labeled trichlorfon administered orally ... /was/ eliminated in urine, about 65% of administered dose ... /was/ excreted in 12 hr. ... 75% ... of compound of unknown structure. ... Less than 0.2% of administered dose ... in milk ... Blood contained ... max of 15.1 ug equivalent 2 hr after administration, decreased ... to about 1 ug equivalent after 24 hr.

White-Stevens, R. (ed.). Pesticides in the Environment: Volume 1, Part 1, Part 2. New York: Marcel Dekker, Inc., 1971., p. 175


The absorption, distribution, and excretion of trichlorfon in mammals is rapid: about 70-80% of a dose administered orally to mice was excreted during the first 12 hr after treatment. The biological half-life of trichlorfon was 80 min. ...3 hr after an iv injection of (14)CH3O-trichlorfon to rats, trace amounts of radioactivity were found in the liver, lungs, kidney, heart, spleen and blood.

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. V30 216 (1983)


For more Absorption, Distribution and Excretion (Complete) data for Trichlorfon (15 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

Trichlorfon and dichlorvos levels were followed in plasma and RBCs of 7 individuals given single oral doses of 7.5-10 mg/kg trichlorfon repeated after 2 wk for treating schistosomiases. The relationship of dichlorvos to trichlorfon in plasma and RBCs was about 1%. A biphasic curve for the elimination of trichlorfon in plasma developed; the first phase had a half-life of 0.4 to 0.6 hr, and the second phase had a half-life of about 3 hr. Clearance of trichlorfon was primarily due to formation of dichlorvos.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 929


... Trichlorfon (and its /metabolic/ product dichlorvos) is very rapidly absorbed and cleared in humans. After acute oral treatment of healthy male volunteers with a 2, 5, 7.5, or 12 mg/kg dose of trichlorfon (metrifonate), the maximum blood concentration of trichlorfon was obtained between 12 min and 2 hr and the half-life in blood was about 2 hr. The concentrations of dichlorvos ... closely followed those of trichlorphon at a constant ratio of about 1 to 100. The concentrations of trichlorfon were detectable up to 8 hr, but those of dichlorvos had fallen bellow the level of detection by then. Both plasma and RBC cholinesterases were readily inhibited and were still low after 24 hr - none of the volunteers complained of side effects (and the half-life of ... dichlorvos was about 3.8 hr).

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 929


The predominant metabolic pathway that involves cleavage of the P-C phosphonate bond that generates trichloroethanol and dimethyl phosphate which are then excreted in urine. Quantitatively minor pathways of metabolism include demethylation ... and (nonenzymatic) dehydrochlorination of dichlorvos which is rapidly metabolized to dichloroethanol and dimethyl phosphate which are then excreted in urine.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 929


Dichlorvos was detected in the brain of mice after ip injection of trichlorfon. Following dermal and intragastric application of trichlorfon to cows, the parent compound and dichlorvos were detected in the milk up to 22 days after application.

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. V30 216 (1983)


For more Metabolism/Metabolites (Complete) data for Trichlorfon (13 total), please visit the HSDB record page.


5.5 Biological Half-Life

...The half-time of trichlorfon in human plasma is approximately 2 hours.

Joint FAO/WHO Expert Committee on Food Additives; WHO Food Additives Series 45: Trichlorfon (2000). Available from, as of February 23, 2006: https://www.inchem.org/documents/jecfa/jecmono/v45je05.htm


The biological half-life of trichlorfon was 80 min /in mice/.

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. V30 216 (1983)


... Following a 133 mg/kg oral dose, trichlorfon was not detected ... Calculated half-lives /of dichlorvos (a nonenzymatic breakdown product of trichlorfon)/ in /rat/ blood, adipose tissue, muscle, and liver were 7, 11, 10, and 12 days, respectively.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 929


After acute oral treatment of healthy male volunteers with a 2, 5, 7.5, or 12 mg/kg dose of trichlorfon (metrifonate) ... the half-life of ... dichlorvos /in blood/ was about 3.8 hr ...

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V7 929


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