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0, 0-Dimethyl 0-2,2-dichlorovinyl phosphate
Also known as: 62-73-7, Ddvp, 2,2-dichloroethenyl dimethyl phosphate, Dichlorophos, Divipan, Vapona
Molecular Formula
C4H7Cl2O4P
Molecular Weight
220.97  g/mol
InChI Key
OEBRKCOSUFCWJD-UHFFFAOYSA-N
FDA UNII
7U370BPS14

An organophosphorus insecticide that inhibits ACETYLCHOLINESTERASE.
1 2D Structure

0, 0-Dimethyl 0-2,2-dichlorovinyl phosphate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2,2-dichloroethenyl dimethyl phosphate
2.1.2 InChI
InChI=1S/C4H7Cl2O4P/c1-8-11(7,9-2)10-3-4(5)6/h3H,1-2H3
2.1.3 InChI Key
OEBRKCOSUFCWJD-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COP(=O)(OC)OC=C(Cl)Cl
2.2 Other Identifiers
2.2.1 UNII
7U370BPS14
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ddvp

2. Dichlofos

3. Dichlorophos

4. Dimethyl Dichlorovinyl Phosphate

5. Divipan

6. Novotox

7. Phosphoric Acid 2,2 Dichloroethenyl Dimethyl Ester

8. Phosphoric Acid 2,2-dichloroethenyl Dimethyl Ester

2.3.2 Depositor-Supplied Synonyms

1. 62-73-7

2. Ddvp

3. 2,2-dichloroethenyl Dimethyl Phosphate

4. Dichlorophos

5. Divipan

6. Vapona

7. 2,2-dichlorovinyl Dimethyl Phosphate

8. Chlorvinphos

9. Brevinyl

10. Canogard

11. Dichlorphos

12. Equigard

13. Krecalvin

14. Lindanmafu

15. Atgard

16. Bibesol

17. Equigel

18. Fecama

19. Herkal

20. Herkol

21. Nerkol

22. Phosvit

23. Unifos

24. Nogos

25. Nuvan

26. Dichlorman

27. Dichlorovos

28. Estrosel

29. Szklarniak

30. Vaponite

31. Vinylofos

32. Vinylophos

33. Winylophos

34. Dedevap

35. Fekama

36. Marvex

37. Mopari

38. Novotox

39. Tenac

40. Task

41. Atgard C

42. Atgard V

43. Nogos G

44. Vapona Insecticide

45. Dichloorvo

46. Astrobot

47. Cekusan

48. Dichlofos

49. Panaplate

50. Tetravos

51. Apavap

52. Benfos

53. Cypona

54. Unitox

55. Ddvp (insecticide)

56. Insectigas D

57. Dimethyl 2,2-dichlorovinyl Phosphate

58. Nogos 50

59. Unifos (pesticide)

60. Derribante

61. Dichlorfos

62. Diclorvos

63. Equiguard

64. Estrosol

65. Nefrafos

66. Deriban

67. Devikol

68. Phosphoric Acid, 2,2-dichloroethenyl Dimethyl Ester

69. Tap 9vp

70. Fly Fighter

71. Mafu Strip

72. Phosphoric Acid, 2,2-dichlorovinyl Dimethyl Ester

73. No-pest Strip

74. Fly-die

75. No-pest

76. Vapora Ii

77. Dimethyldichlorovinyl Phosphate

78. Nuvan 7

79. O,o-dimethyl Dichlorovinyl Phosphate

80. Oms 14

81. Xlp 30

82. Dichlorovas

83. Duravos

84. Equigand

85. Verdican

86. Verdipor

87. Verdisol

88. Algard

89. Dimethyl 2,2-dichloroethenyl Phosphate

90. Unifos 50 Ec

91. Sd 1750

92. Sd-1750

93. Nci-c00113

94. Nogos 50 Ec

95. Nuvan 100ec

96. Task Tabs

97. Nsc-6738

98. Bay-19149

99. Dimethyl Dichlorovinyl Phosphate

100. Bayer 19149

101. Brevinyl E-50

102. Ddvf

103. Phosphoric Acid 2,2-dichloroethenyl Dimethyl Ester

104. Nsc 6738

105. Ethenol, 2,2-dichloro-, Dimethyl Phosphate

106. Dimethyl-2,2-dichlorovinyl Phosphate

107. (2,2-dichloro-vinil)dimetil-fosfato

108. Brevinyl E 50

109. (2,2-dichlor-vinyl)-dimethyl-phosphat

110. Atgard (tn)

111. Phosphate De Dimethyle Et De 2,2-dichlorovinyle

112. Vinyl Alcohol, 2,2-dichloro-, Dimethyl Phosphate

113. O,o-dimethyl 2,2-dichlorovinyl Phosphate

114. Nuvan 100 Ec

115. Ent-20738

116. Phosphoric Acid 2,2-dichlorovinyl Dimethyl Ester

117. Phosphate, 2-2-dichlorovinyl Dimethyl

118. 2,2-dichloroethenyl Phosphoric Acid Dimethyl Ester

119. (2,2-dichloor-vinyl)-dimethyl-fosfaat

120. Chembl167911

121. Chebi:34690

122. O,o-dimethyl-o-(2,2-dichlor-vinyl)-phosphat

123. Nsc6738

124. (2,2-dichloor-vinyl)-dimethyl-fosfaat [dutch]

125. 7u370bps14

126. 2,2-dimethyldichlorovinyl Phosphate

127. Oko

128. Ncgc00090997-02

129. Denkavepon

130. Uniphos

131. Dsstox_cid_449

132. O-(2,2-dichlorvinyl)-o,o-dimethylphosphate

133. Des (phosphate)

134. Dsstox_rid_75598

135. Dsstox_gsid_20449

136. Brevinyl E50

137. Dichloorvo [dutch]

138. Dichlorfos [polish]

139. Caswell No. 328

140. Dichlorvosum

141. Delevap

142. Derriban

143. Mafu

144. Nuva

145. Diclorvos [inn-spanish]

146. Dichlorvosum [inn-latin]

147. Cas-62-73-7

148. Dichlorvos [iso]

149. Ccris 230

150. Dichlorvos [usan:inn:ban]

151. Dichlorvos (ddvp)

152. Udvf

153. Hsdb 319

154. Bay-b 4986

155. (2,2-dichloor-vinyl)-dimethyl-fosfaat (dutch)

156. Dichlorvos [bsi:iso]

157. Einecs 200-547-7

158. Ent 20738

159. Epa Pesticide Chemical Code 084001

160. Brn 1709141

161. Dichlorovinphos

162. Aquaguard

163. Nuvos

164. Unii-7u370bps14

165. Ai3-20738

166. O,o-dimethyl O-2,2-dichlorovinyl Phosphate

167. Dichloroethenyl Dimethyl Phosphate

168. Prima U

169. (2,2-dichloro-vinil)dimetil-fosfato [italian]

170. (2,2-dichlor-vinyl)-dimethyl-phosphat [german]

171. O,o-dwumetylo-o-dwuchlorowinylofosforan [polish]

172. Dichlorvos (vapona)

173. O-(2,2-dichlorvinyl)-o,o-dimethylphosphat [german]

174. Dichlorfos(polish)

175. 2,2-dichloroethenol Dimethyl Phosphate

176. O,o-dimethyl-o-(2,2-dichlor-vinyl)-phosphat [german]

177. O,o-dwumetylo-o-dwuchlorowinylofosforan

178. Phosphate De Dimethyle Et De 2,2-dichlorovinyle [french]

179. Spectrum_001779

180. Dimethyl O,2-phosphate

181. 2,2-dichlorovinyl-o,o-dimethyl Phosphate

182. Dichlorvos [mi]

183. Specplus_000360

184. Dichlorvos [inn]

185. Dichlorvos (usan/inn)

186. O-(2,2-dichlorvinyl)-o,o-dimethylphosphat

187. O-(2,o-dimethylphosphat

188. Spectrum2_001227

189. Spectrum3_000810

190. Spectrum4_000650

191. Spectrum5_001930

192. Dichlorvos [hsdb]

193. Dichlorvos [iarc]

194. Dichlorvos [usan]

195. 2,2-dichlorovinyl Alcohol Dimethyl Phosphate

196. Dichlorvos [mart.]

197. 0,2-dichlorovinyl Phosphate

198. 2,2-dichlorovinyl Dimethyl Phosphoric Acid Ester

199. Dichlorvos [usp-rs]

200. Dichlorvos [who-dd]

201. Schembl25067

202. Bspbio_002279

203. Kbiogr_000999

204. Kbioss_002260

205. O,2-dichlor-vinyl)-phosphat

206. Mls002222471

207. Bidd:er0583

208. Divk1c_006456

209. Spbio_001074

210. Dichlorvos [green Book]

211. Wln: Gygu1opo&o1&o1

212. Dtxsid5020449

213. Kbio1_001400

214. Kbio2_002259

215. Kbio2_004827

216. Kbio2_007395

217. Kbio3_001779

218. Oebrkcosufcwjd-uhfffaoysa-

219. Hms2091c21

220. Dimethyl 2,2-dichlorovinylphosphate

221. Zinc1853865

222. Tox21_111052

223. Tox21_201617

224. Tox21_300840

225. Bdbm50286926

226. Ccg-39147

227. Mfcd00036123

228. P5d635

229. (2, 2-dichloro-vinil)dimetil-fosfato

230. (2,2-dichlorovinyl)-dimethyl-fosfate

231. Akos005111045

232. Tox21_111052_1

233. Db11397

234. Dichlorvos 100 Microg/ml In N-hexane

235. Dichlorvos 1000 Microg/ml In Acetone

236. Ethenol,2-dichloro-, Dimethyl Phosphate

237. (2, 2-dichlor-vinyl)-dimethyl-phosphat

238. Ncgc00090997-01

239. Ncgc00090997-03

240. Ncgc00090997-04

241. Ncgc00090997-05

242. Ncgc00090997-06

243. Ncgc00090997-07

244. Ncgc00090997-08

245. Ncgc00090997-09

246. Ncgc00090997-11

247. Ncgc00254743-01

248. Ncgc00259166-01

249. Dichlorvos 100 Microg/ml In Acetonitrile

250. Dimethyl O,o-dichlorovinyl-2,2-phosphate

251. Smr000777927

252. Sbi-0052506.p003

253. 2,2-dichlorovinyl Dimethyl Phosphate, 8ci

254. Db-054265

255. Dimethyl O, O-dichlorovinyl-2,2-phosphate

256. 2,2-bis(chloranyl)ethenyl Dimethyl Phosphate

257. O-(2, 2-dichlorvinyl)-o,o-dimethylphosphat

258. O-o-dimethyl-o(2,2-dichlorovinyl)phosphate

259. Dichlorvos, Pestanal(r), Analytical Standard

260. Ethenol, 2, 2-dichloro-, Dimethyl Phosphate

261. Phosphoric Acid,2-dichlorovinyl Dimethyl Ester

262. Vinyl Alcohol,2-dichloro-, Dimethyl Phosphate

263. 0, 0-dimethyl 0-2,2-dichlorovinyl Phosphate

264. D03791

265. Ab00053012_02

266. O,o-dimethyl-o-(2, 2-dichlor-vinyl)-phosphat

267. Phosphoric Acid,2-dichloroethenyl Dimethyl Ester

268. A833962

269. Q420622

270. Sr-05000001548

271. Sr-05000001548-1

272. O-(2,2-dichloroethenyl) O,o-dimethyl Phosphate, 9ci

273. Dichlorvos, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 220.97 g/mol
Molecular Formula C4H7Cl2O4P
XLogP31.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass219.9459011 g/mol
Monoisotopic Mass219.9459011 g/mol
Topological Polar Surface Area44.8 Ų
Heavy Atom Count11
Formal Charge0
Complexity181
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 Therapeutic Uses

Anthelmintics; Cholinesterase Inhibitors; Insecticides

National Library of Medicine's Medical Subject Headings. Chloramphenicol. Online file (MeSH, 2017). Available from, as of May 17, 2017: https://www.nlm.nih.gov/mesh/2017/mesh_browser/MBrowser.html


VET: Anthelmintic; ectoparasiticide.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 558


VET: Dichlorvos is used primarily to treat intestinal parasites. Parasites that may be treated include Toxocara canis and Toxascaris leonina (roundworms), Ancylostoma caninum, Uncinaria stenocephala (hookworms), and Trichuris vulpis (whipworms). However, efficacy against T. vulpis may be erratic. In horses, it may be used for the removal and control of bots (Gastrophilus intestinalis, G. nasalis), large strongyles (Strongylus vulgaris, S. equinus, S. edentatus), small strongyles (of the genera Cyathostomum, Cylicocerus, Cylicodontophorus, Triodontophorus, Poteriostomum), pinworms (Oxyuris equi), and large roundworm (Parascaris equorum). In pigs, it is used to treat and control mature, immature, and/or fourth-stage larvae of the whipworm (Trichuris suis), nodular worm (Oesophagostomum sp.), large roundworm (Ascaris suum), and the thick stomach worm (Ascarops strongylina).

Papich, M.G. Saunders Handbook of Veterinary Drugs Small and Large Animal. 3rd ed. St. Louis, MO: Elsevier Saunders, 2011, p. 221


VET: A cholinesterase inhibitor, it is used in flea (pest) collars for pets.

Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 1223


For more Therapeutic Uses (Complete) data for Dichlorvos (8 total), please visit the HSDB record page.


4.2 Drug Warning

VET: Overdoses can cause organophosphate intoxication (treat with pralidoxime chloride and atropine). Signs of toxicity include salivation, diarrhea, difficulty breathing, and muscle twitching.

Papich, M.G. Saunders Handbook of Veterinary Drugs Small and Large Animal. 3rd ed. St. Louis, MO: Elsevier Saunders, 2011, p. 222


VET: Do not use in patients with heartworms. Do not administer within 2 days of administration of a cholinesterase-inhibiting drug. Use a split-dosage schedule in animals that are old, heavily parasitized, anemic, or otherwise debilitated. Do not use in young foals, kittens, or puppies. Its use may exacerbate clinical signs in animals with respiratory disease, such as bronchitis and obstructive pulmonary disease. Do not allow birds access to feed containing this preparation or to fecal excrement from treated animals.

Papich, M.G. Saunders Handbook of Veterinary Drugs Small and Large Animal. 3rd ed. St. Louis, MO: Elsevier Saunders, 2011, p. 222


Do not use with other anticholinesterase drugs. Do not use with other antifilarial agents, muscle relaxants, CNS depressants, or tranquilizers.

Papich, M.G. Saunders Handbook of Veterinary Drugs Small and Large Animal. 3rd ed. St. Louis, MO: Elsevier Saunders, 2011, p. 222


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 Absorption, Distribution and Excretion

At least 85% of an oral dose of dichlorvos is absorbed. Dichlorvos is well absorbed following inhalation exposure based on the occurrence of toxic symptoms associated with inhalation exposures and the detection of specific dichlorvos metabolites (dichloroethanol and dimethyl phosphate) in urine of individuals exposed to 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 820


An elimination half-life of 13.5 min was estimated based on dichlorvos concentration in rat kidney after 2 or 4 hr exposure to 5 mg/cu m. In mice and rats given single oral doses of dichlorvos, 59-65% was eliminated in urine, 3-7% was eliminated in feces, 14-18% was eliminated as CO2 by 4 days after dosing, and the vast majority was eliminated by 24 hr. Retained dichlorvos following either oral or inhalation exposure is high because it is incorporated into intermediary metabolism.

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 820


The vinyl moiety of the dichlorvos molecule undergoes two routes of biotransformation: conversion to dichloroethanol and subsequent formation of dichloroethanol glucuronide; or dehalogenation and incorporation of the carbon atoms into various metabolic pathways in the body. These pathways result in the production of hippuric acid, urea, carbon dioxide, and other endogenous compounds that result in a prolonged half-life of radioactivity in the tissues following the administration of [vinyl-C14] dichlorvos. Both radiolabelled dichloroethanol glucuronide and urea have been identified in the urine of men treated with [vinyl-C14] dichlorvos indicating that both pathways occur in humans.

DHHS/ATSDR; Toxicological Profile for Dichlorvos p.71 (PB/98/101124/AS) (September 1997)


Dichlorvos was undetectable (<0.1 mg/liter) in the blood of two men immediately after exposure, one to air concentrations of 0.25 mg dichlorvos/cu m for 10 hours and one to 0.7 mg dichlorvos/cu m for 20 hours.

WHO; Environ Health Criteria 79: Dichlorvos p.37 (1988)


For more Absorption, Distribution and Excretion (Complete) data for Dichlorvos (8 total), please visit the HSDB record page.


5.3 Metabolism/Metabolites

Dichlorvos binds to acetylcholinesterase forming dimethoxy-phosphorylated acetycholinesterase and dichloroacetaldehyde. Alternatively, it is metabolized (primarily in the liver but also in the blood, adrenal, kidney, lung, and spleen) via 2 pathways. The major pathway is catalyzed by A-esterases and produces dimethyl phosphate and dichloroacetaldehyde. Dichloroacetaldehyde is converted to dichloroethanol which is then excreted as the glucuronide. Alternatively, dichloroacetaldehyde is dehalogenated and the carbon atoms are incorporated into normal tissue constituents via intermediary metabolism. The second minor pathway is catalyzed by glutahione-S-transferase and produced desmethyl dichlorvos and S-methyl glutathione. Subsequent degradation of desmethyl dichlorvos to dichloroacetaldehyde and monomethyl phosphate is catalyzed by A-esterases. S-methyl glutathione is broken down to methylmercapturic acid and excreted in urine. CO2 is also the major metabolite following inhalation exposures. The major urinary metabolite following either oral or inhalation exposures is dichloroethanol glucuronide.

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 820


Dichlorvos is rapidly metabolized in human blood by A-esterases ... Dichlorvos A-esterase appears to be normally distributed. Half-lives for degradation of dichlorvos in whole blood after inhalation were 8.1 min for men and 11.2 min for women.

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 820


Dichlorvos (DDVP) is a methylating agent. DNA from mice given 1.9 x 10-6 mol/kg of DDVP, degree of alkylation of guanine-n-7 accounting to 8 x 10-13 mol methyl per gram of DNA was found. Rate of clearance was (estimated) to be 29 hr .

Segerback D, Ehenberg L; Acta Pharmacol Toxicol 49 (Suppl 5): 56-66 (1981)


Dichlorvos, one of the active metabolites of trichlorofon ... is hydrolyzed to give dimethyl phosphate and dichloroacetaldehyde. The latter is subsequently reduced to beta,beta-dichloroethyl alcohol, characteristically converted by rats when administered intraperitoneally. After hydrolysis to a two-carbon fragment, dichloroacetaldhyde is able to enter a pathway of intermediary metabolism, and carbon dioxide is the major radioactive metabolic.

Aizawa, H. Metabolic Maps of Pesticides. New York, NY: Academic Press, 1982., p. 154


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


5.4 Biological Half-Life

Half-lives for degradation of dichlorvos in whole blood after inhalation were 8.1 min for men and 11.2 min for women.

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 820


An elimination half-life of 13.5 min was estimated based on dichlorvos concentration in rat kidney after 2 or 4 hr exposure to 5 mg/cu m.

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 820


5.5 Mechanism of Action

Like other organophosphate agents, dichlorvos inhibits acetylcholinesterase interfering with neuromuscular transmission in susceptible parasites.

Plumb D.C. Veterinary Drug Handbook. 8th ed. (pocket). Ames, IA: Wiley-Blackwell, 2015., p. 431


Dichlorvos is the active molecule of the pro-drug metrifonate used to revert the cognitive deficits associated with Alzheimer's disease. A few years ago it was reported that dichlorvos inhibits the enzyme acylpeptide hydrolase at lower doses than those necessary to inhibit acetylcholinesterase to the same extent. Therefore, the aim of our investigation was to test the hypothesis that dichlorvos can enhance synaptic efficacy through a mechanism that involves acylpeptide hydrolase instead of acetylcholinesterase inhibition. We used long-term potentiation induced in rat hippocampal slices as a model of synaptic plasticity. Our results indicate that short-term exposures (20 min) to 50 uM dichlorvos enhance long-term potentiation in about 200% compared to the control condition. This effect is correlated with approximately 60% inhibition of acylpeptide hydrolase activity, whereas acetylcholinesterase activity remains unaffected. Paired-pulse facilitation and inhibition experiments indicate that dichlorvos does not have any presynaptic effect in the CA3-->CA1 pathway nor affect gabaergic interneurons. Interestingly, the application of 100 nM methyllicaconitine, an alpha(7) nicotinic receptor antagonist, blocked the enhancing effect of dichlorvos on long-term potentiation. These results indicate that under the exposure conditions described above, dichlorvos enhances long-term potentiation through a postsynaptic mechanism that involves (a) the inhibition of the enzyme acylpeptide hydrolase and (b) the modulation of alpha(7) nicotinic receptors.

PMID:19379766 Olmos C et al; Toxicol Appl Pharmacol 238 (1): 37-46 (2009)


Exposure to dichlorvos (DDVP), an organophosphorus pesticide, is known to result in neurotoxicity as well as other metabolic perturbations. However, the molecular causes of DDVP toxicity are poorly understood, especially in cells other than neurons and muscle cells. To obtain a better understanding of the process of non-neuronal DDVP toxicity, we exposed zebrafish to different concentrations of DDVP, and investigated the resulting changes in liver histology and gene transcription. Functional enrichment analysis of genes affected by DDVP exposure identified a number of processes involved in energy utilization and stress response in the liver. The abundance of transcripts for proteins involved in glucose metabolism was profoundly affected, suggesting that carbon flux might be diverted toward the pentose phosphate pathway to compensate for an elevated demand for energy and reducing equivalents for detoxification. Strikingly, many transcripts for molecules involved in beta-oxidation and fatty acid synthesis were down-regulated. We found increases in message levels for molecules involved in reactive oxygen species responses as well as ubiquitination, proteasomal degradation, and autophagy. To ensure that the effects of DDVP on energy metabolism were not simply a consequence of poor feeding because of neuromuscular impairment, we fasted fish for 29 or 50 hr and analyzed liver gene expression in them. The patterns of gene expression for energy metabolism in fasted and DDVP-exposed fish were markedly different. We observed coordinated changes in the expression of a large number of genes involved in energy metabolism and responses to oxidative stress. These results argue that an appreciable part of the effect of DDVP is on energy metabolism and is regulated at the message level. Although we observed some evidence of neuromuscular impairment in exposed fish that may have resulted in reduced feeding, the alterations in gene expression in exposed fish cannot readily be explained by nutrient deprivation.

PMID:26499117 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4619386 Bui-Nguyen TM et al; BMC Genomics 16: 853 (2015)


The main target of neurotoxins is neurons because they comprise the main part of neural function, but glial cells may be indirect targets because they support the function of neurons. Among the glial cells, astrocytes in particular act as "nurse cells", regulating neuronal survival and functions. In the present study, to reveal whether a known neurotoxic substance, organophosphate dichlorvos (DDVP), affects the differentiation of astrocytes, we used an astrocyte differentiation model in rat glioma C6 cells. Morphological change and induction of GFAP expression in the differentiating C6 cells were suppressed by DDVP treatment. The known potential targets of DDVP are acetylcholine esterase (AChE), fatty acid amide hydrolase and methyl guanine methyl transferase. Among the specific inhibitors against these enzymes, the AChE inhibitor paraoxon successfully suppressed the cellular morphological changes and the induction of GFAP expression in differentiating C6 cells. These results indicate that DDVP inhibits differentiation in the C6 astrocyte-differentiation model, in which at least AChE inhibition is involved and that AChE is a potent regulator of the differentiation. Furthermore, considering that the main substrate of AChE is ACh, thus, ACh may act as regulators of astrocyte differentiation.

PMID:24001591 Ozawa A et al; Brain Res 1537: 37-45 (2013)


For more Mechanism of Action (Complete) data for Dichlorvos (7 total), please visit the HSDB record page.


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