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1. Alpha-cypermethrin
2. Alphacypermethrin
3. Alphamethrin
4. Beta-cipermetrina
5. Cymbush
6. Cypermethrin, (1alpha(s*),3alpha)-(+-)-isomer
7. Cypermethrin, (1r-(1alpha(r*),3beta))-isomer
8. Cypermethrin, (1r-(1alpha(s*),3beta))-isomer
9. Fastac 50ec
10. Fendona
11. Nrdc 149
12. Supercypermethrin
13. Supermethrin
14. Wl 85871
15. Wl-85871
1. 52315-07-8
2. Supercypermethrin
3. Alpha-cypermethrin
4. Ripcord
5. Ammo
6. Beta-cypermethrin
7. Cypermethrine
8. Basathrin
9. Cymbush
10. Ustaad
11. Agrothrin
12. Creokhin
13. Cymperator
14. Cypercopal
15. Cyperkill
16. Cypersect
17. Flectron
18. Hilcyperin
19. Neramethrin
20. Polytrin
21. Arrivo
22. Cyperco
23. Kordon
24. Mustang
25. Sherpa
26. Siperin
27. Toppel
28. Ardap
29. Demon
30. Excis
31. Fenom
32. Colt
33. Cis-cypermethrin
34. Ambush C
35. Nrdc 149
36. Zeta-cypermethrin
37. Supercypermethrin Forte
38. Alphamethrin
39. 67375-30-8
40. .alpha.-cypermethrin
41. Cypermethrin [ban]
42. Nrdc-149
43. 137497-61-1
44. Fmc 30980
45. Fmc 45806
46. Pp 383
47. Chinmix
48. Cyclopropanecarboxylic Acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, Cyano(3-phenoxyphenyl)methyl Ester
49. Wl 43467
50. Nsc-760420
51. [cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
52. Cyano(3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
53. Chebi:4042
54. Fury
55. 1tr49121np
56. Cypermethrin (ban)
57. Alpha-cyano-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
58. Alphamethrine
59. Ncgc00160389-02
60. Asymmethrin
61. Cypercare
62. Cyperil
63. Ectopor
64. Kreokhin
65. Rycopel
66. Dysect
67. Nurele
68. Cypor
69. Cyrux
70. Drago
71. Topclip Parasol
72. Cypermethrin, High Effect
73. Fury Insecticide
74. Kalif Super
75. Dsstox_cid_3998
76. Cympa-ti
77. Ambush Cy
78. Ammo (pesticide)
79. Demon Tc
80. Dsstox_rid_77252
81. Barricade 10ec
82. Cypermethrin-25ec
83. Dsstox_gsid_23998
84. Fenom (pesticide)
85. 86753-92-6
86. Alpha-cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
87. Ai3-29295
88. Dudu Alpha
89. Antiborer 3767
90. Neramethrin Ec 50
91. Cypermetryna [polish]
92. Cypermetryna
93. Vucht 424
94. Wrdc149
95. Barricade (insecticide)
96. Caswell No. 268aa
97. Fastac Duo; Fendona; Fendona 65c; Mageos; Ultimate; Wl 85871
98. Beta Cypermethrin
99. Cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
100. Cypermethrine [iso-french]
101. Cas-52315-07-8
102. Ccn 52
103. Ccris 2499
104. Cypermethrin [ansi:bsi:iso]
105. Ecofleece Sheep Dip (non-op)
106. Hsdb 6600
107. [(s)-cyano-(3-phenoxyphenyl)methyl] (1s,3r)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
108. Exp 5598
109. Jf 5705f
110. Einecs 257-842-9
111. Fmc 45497
112. Yt 305
113. Epa Pesticide Chemical Code 109702
114. Epa Pesticide Chemical Code 129064
115. Wl 8517
116. Brn 2422506
117. Aimcocyper
118. Cypromethin
119. Folcord
120. Prevail
121. Ralothrin
122. Ru 27998
123. Sf 06646
124. Unii-1tr49121np
125. Kafil Super
126. Ccris 4067
127. Fligene Ci
128. Wl85871
129. Zetagard (tn)
130. 97955-44-7
131. Alpha -cypermethrin
132. Cypermethrin, Solid
133. .zeta.-cypermethrin
134. Spectrum_001862
135. Cypermethrin, .zeta.-
136. Specplus_000718
137. Spectrum5_001858
138. Cypermethrin [mi]
139. Cypermethrin [iso]
140. Cypermethrin [hsdb]
141. (+-)-alpha-cyano-3-phenoxybenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropane Carboxylate
142. Ccn52
143. Cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcycloptopanecarboxylate
144. Schembl21972
145. Bmk1-h8
146. Bspbio_001598
147. Cypermethrin [mart.]
148. Kbiogr_000318
149. Kbioss_000318
150. Kbioss_002379
151. (+)-alpha-cyano-3-phenoxybenzyl-(+)-cis,trans-2,2-dichlorovinyl-2,2-dimethylcyclopropanecarboxylate
152. (+-)-alpha-cyano-3-phenoxybenzyl-(+-)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane Carboxylate
153. (rs)-alpha-cyano-3-phenoxybenzyl (1rs)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
154. 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic Acid Cyano(3-phenoxyphenyl)-, Methyl Ester
155. Cypermethrin [who-dd]
156. Divk1c_006814
157. Chembl373204
158. Dtxsid1023998
159. Bcbcmap01_000010
160. Kbio1_001758
161. Kbio2_000318
162. Kbio2_002375
163. Kbio2_002886
164. Kbio2_004943
165. Kbio2_005454
166. Kbio2_007511
167. Kbio3_000635
168. Kbio3_000636
169. Cypermethrin, >=98% (hplc)
170. Bio1_000414
171. Bio1_000903
172. Bio1_001392
173. Bio2_000318
174. Bio2_000798
175. Hms1361p20
176. Hms1791p20
177. Hms1989p20
178. Hms3264o17
179. Hms3402p20
180. Pharmakon1600-01503606
181. Tox21_113579
182. Tox21_300892
183. Mfcd00055328
184. Nsc760420
185. Akos015899999
186. Tox21_113579_1
187. Ccg-213883
188. Db13721
189. Ks-5077
190. Nsc 760420
191. [cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropanecarboxylate
192. Cypermethrin 10 Microg/ml In Isooctane
193. Idi1_034068
194. Ncgc00160389-01
195. Ncgc00160389-03
196. Ncgc00160389-04
197. Ncgc00160389-05
198. Ncgc00160389-06
199. Ncgc00160389-07
200. Ncgc00160389-09
201. Ncgc00163438-01
202. Ncgc00254796-01
203. (rs)-alpha-cyano-3-phenoxybenzyl (1rs,3rs)-(1rs,3rs)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
204. Ac-22284
205. Cypermethrin 100 Microg/ml In Cyclohexane
206. Sbi-0051832.p002
207. (s)-alpha-cyano-3-phenoxybenzyl(1rs,3rs
208. Cypermethrin 100 Microg/ml In Acetonitrile
209. Ft-0603149
210. Ft-0603150
211. Ft-0773601
212. 15c078
213. D07763
214. Ab00052361_02
215. Cypermethrin, Pestanal(r), Analytical Standard
216. Q412024
217. Sr-01000872736
218. Sr-01000872736-1
219. Alpha-cypermethrin, Pestanal(r), Analytical Standard
220. Cypermethrin, Certified Reference Material, Tracecert(r)
221. (1rs)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
222. 1rs,3sr)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxylate
223. Alpha-cyano-3-phenoxybenzyl 2-(2',2'-dichlorovinyl)-3,3-dimethylcyclopropanecarboxylate
224. Alpha-cyano-3-phenoxybenzyl 2-(2,2-dichlorovinyl)-3,3-dimethylcyclopropanecarboxylate
225. Alpha-cyano-3-phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
226. Cyano(3-phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate #
227. Cypermethrin Solution, 100 Mug/ml In Acetonitrile, Pestanal(r), Analytical Standard
228. (rs)-.alpha.-cyano-3-phenoxybenzyl (1rs,3rs)-(1rs,3rs)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
229. 3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropane Carboxylic Acid, Cyano (3-phenoxy-phenyl) Methyl Ester
230. 3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclopropanecarboxylic Acid Cyano-(3-phenoxy-phenyl)-methyl Ester
231. 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic Acid, Cyano(3-phenoxyphenyl)methyl Ester
232. 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane-1-carboxylic Acid 3-phenoxy-alpha-cyano-benzyl Ester
233. Cyclopropanecarboxylic Acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-,cyano(3-phenoxyphenyl)methyl Ester
| Molecular Weight | 416.3 g/mol |
|---|---|
| Molecular Formula | C22H19Cl2NO3 |
| XLogP3 | 6 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 7 |
| Exact Mass | 415.0741989 g/mol |
| Monoisotopic Mass | 415.0741989 g/mol |
| Topological Polar Surface Area | 59.3 Ų |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Complexity | 643 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 3 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
Therapeutic Category (Veterinary): ectoparasiticide
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 464
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.)
P - Antiparasitic products, insecticides and repellents
P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents
P03B - Insecticides and repellents
P03BA - Pyrethrines
P03BA02 - Cypermethrin
On single oral administration of each of (14)C-(1RS)-trans- and (1RS)-cis-cypermethrin labeled in the benzyl ring, the cyclopropane ring, or the CN group to male and female rats at 1-5 mg/kg, carbon-14 from the acid and alcohol moieties was rapidly and almost completely excreted into the urine and feces. The carbon-14 from the CN group was relatively slowly excreted in the urine and feces, the total recovery being 50-67%. The tissue residues of rats treated with the acid- or alcohol-labeled preparations were generally very low except for the fat (ca. 1 ppm). In contrast, the CN-labeled preparation showed relatively high residue levels, especially in the stomach (contents), intestines, and skin.
Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 2, 2nd ed. 2001. Academic Press, San Diego, California., p. 1268
Dermal exposure to cypermethrin during spray application at up to 46 mg/hr led to an estimation that approximately 3% was absorbed.
Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 2. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 594
Exposure to cypermethrin & its absorption during aerial spraying of an ultra low volume formulation were studied. A contract pilot & mixer/loader at each of two commercial cotton farms in Mississippi were monitored for dermal exposure to cypermethrin during 12 aerial spray applications. Each operation consisted of 1 mixing/loading operation & 1 application of 50 gal of dilute spray soln for about 30 min. Three volunteer mixer/loaders collected their total urine output for 24 hr periods from 1 or 2 days before to 6 days after exposure. Absorption of cypermethrin was evaluated by determining cypermethrin urinary metabolites. All mixer/loaders wore protective equipment. Total potential & actual dermal exposures were estimated. Avg potential exposures (protected & exposed skin) were 1.07 & 10.5 mg/8 hr day (mg/day) for pilots & mixer/loaders, respectively. Actual skin exposures averaged 0.67 mg/day for pilots & 2.43 mg/day for mixer/loaders. 67% of the total potential exposures to pilots occurred on the hands. For the mixer/loaders, exposure involved primarily the arms, trunk, & hands, amounting to 37, 24, & 17% of total exposure, respectively. Absorption by mixer/loaders determined from analyses of urinary metabolites amounted to 46 to 78 ug cypermethrin equivalents per 3 mixed loads & per 12 simulated mixed loads. /It was/ concluded that exposure of pilots & mixer/loaders during aerial application of ultra low volumes is minimal. Only a small proportion of the cypermethrin that contacts the skin is absorbed.
Chester G et al; Arch of Environ Contam and Toxicol 16 (1): 69-78 (1987)
1. Dose excretion studies with cypermethrin (as a 1:1 cis/trans mixture) & alphacypermethrin (1 of the 2 disastereoisomer pairs which constitute cis cypermethrin) were carried out with, in each case, 2 volunteers/dose level. The studies included (a) single oral alphacypermethrin doses of 0.25 mg, 0.50 mg & 0.75 mg followed by repeated alphacypermethrin doses at the same levels, daily for 5 days, (b) repeated oral cypermethrin doses of 0.25 mg, 0.75 mg & 1.5 mg daily for 5 days, & (c) a single dermal application of 25 mg cypermethrin to the forearm. Urine was monitored for the free & conjugated 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid before & after dosing. 2. Metab & rate of excretion of a single oral dose of alphacypermethrin was similar to that of cis cypermethrin, on average, 43% of the dose was excreted as the cyclopropanecarboxylic acid in the first 24 hr urine. There was no incr in urinary metabolite excretion when alphacypermethrin was admin as a repeated oral dose. Subjects excreted, on average, 49% of the dose as the cyclopropanecarboxylic acid in the subsequent 24 hr periods after dosing. 3. There was no incr in the urinary cyclopropanecarboxylic acid excretion when cypermethrin was admin as a repeated oral dose. Subjects excreted, on average, 72% of the trans isomer dose & 45% of the cis isomer dose respectively in the subsequent 24 hr periods after dosing. 4. Approx 0.1% of the applied dermal dose of 25 mg cypermethrin was excreted within 72 hr as the urinary cyclopropanecarboxylic acid. No conclusions can be drawn from such urinary excretion data as to the concn of cypermethrin & its metabolites in the skin or other organs, or the possibility of other routes of metab or excretion.
Eadsforth CV et al; Xenobiotica 18 (5): 1988 603-14
For more Absorption, Distribution and Excretion (Complete) data for CYPERMETHRIN (9 total), please visit the HSDB record page.
In the case of cypermethrin, the relative importance of an esterase attack as opposed to an oxidative one is more important than for permethrin; for trans-cypermethrin the ratio is 93.2% to 17.3% and for cis-cypermethrin 41.5% to 37.6% in the mouse system. In case of deltamethrin (which has only a cis-isomer) the ratio is 28.3% to 41%. Since the mouse system shows a high oxidative ratio, the above figures seem to indicate that esterase metabolism in these pyrethroids is at least as important as the oxidative ones.
Matsumura, F. Toxicology of Insecticides. 2nd ed. New York, NY: Plenum Press, 1985., p. 286
The major degradation pathway of cypermethrin is hydrolysis of the ester linkage to /yield ultimately/ 3-phenoxybenzoic acid and 3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylic acid. (From the cis-isomer both cis- and trans- cyclopropanecarboxylic acids are found.) A minor degradative route is ring hydroxylation to give an alpha-cyano-3-(4-hydroxyphenyl)benzyl ester followed by hydrolysis to produce the corresponding hydroxycarboxylic acid.
Aizawa, H. Metabolic Maps of Pesticides. New York, NY: Academic Press, 1982., p. 186
When administered to rats and mice, a large part of trans-cypermethrin was eliminated in urine in 24 hr. Under similar conditions, 80% of administered 3-phenoxybenzoic acid was eliminated. When cis-cypermethrin was administered, more was excreted via feces. The major urinary metabolite in mice, from trans-cypermethrin and 3-phenoxybenzoic acid, was identified with the aid of MS and NMR as N-(3-phenoxybenzoyl)taurine. A minor metabolite was identified as the sulfate of 3-(4-hydroxyphenoxy)benzoic acid. The taurine conjugate was not found in the rat urine. In rats, the major metabolite was the sulfate conjugate of 3-(4-hydroxyphenoxy)-benzoic acid. Mouse liver microsomal + NADPH preparations hydroxylated trans- and cis-cypermethrin at the t- and c-methyl groups and the 4' and 5 positions. Hydroxylation at the 5 position of trans-cypermethrin was detected only with microsomes treated with tetraethyl pyrophosphate to inhibit esterase activity.
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. 471
The major metabolic reactions of trans- and cis-cypermethrin were cleavage of ester linkage, oxidation at the trans- and cis-methyl cyclopropane ring and at 4'-position of the phenoxy group, and conversion of the CN group to SCN ion. The following minor species differences were observed: (1) oxidation at 5- and 6-positions of the alcohol moiety was observed in mice but not in rats; (2) ester metabolites such as 2'-OH, 5-OH, and trans-OH,4'-OH-cypermethrin were detected in feces of mice but not of rats. The remarkable species difference in metabolites was the PBacid-taurine conjugate, which was the predominant metabolite in mice, but it was not detected in rats.
Krieger, R. (ed.). Handbook of Pesticide Toxicology. Volume 2, 2nd ed. 2001. Academic Press, San Diego, California., p. 1268
For more Metabolism/Metabolites (Complete) data for CYPERMETHRIN (9 total), please visit the HSDB record page.
Pyrethroid insecticides are synthetic neurotoxins patterned after the naturally occurring pyrethrins. Their mechanism of action is thought to involve effects primarily at the voltage-sensitive sodium channel of both insect & mammalian neurons, although recent studies have raised the possibility that these cmpds may also act at the gamma-aminobutyric acid receptor-chloride ionophore complex. Here we show that active pyrethroids of the alpha-cyano-3-phenoxybenzyl class allosterically enhance the binding of (3)H-batrachotoxinin-A 20-alpha-benzoate to voltage-sensitive sodium channels of rat brain in a dose-dependent & stereospecific manner. Comparison of the rank order of potency for enhancement of (3)H-batrachotoxinin-A 20-alpha-benzoate binding & insecticidal activity in a series of toxic steroisomers of cypermethrin, representative of the class, reveals a correlation between the two measures. These results support a sodium channel site model for pyrethroid action & suggest a useful & practical method to help evaluate the relationship between the sodium channel & insecticidal potency for members of this class of cmpds.
PMID:2455860 Brown GB et al; Mol Pharmacol 34 (1): 54-9 (1988)
Following absorption through the chitinous exoskeleton of arthropods, pyrethrins stimulate the nervous system, apparently by competitively interfering with cationic conductances in the lipid layer of nerve cells, thereby blocking nerve impulse transmissions. Paralysis and death follow. /Pyrethrins/
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2000.Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2000 (Plus Supplements)., p. 3203
The efforts of this study were directed at defining the importance of esterases, mixed function oxidases and mitochondrial respiratory chain enzymes in in vitro covalent binding of cismethrin and the two cyanopyrethroids, cypermethrin and deltamethrin to phenobarbital induced rat liver homogenate and microsomes. Each enzyme system was selectively inhibited to elucidate the activation mechanism involved. Piperonyl-butoxide and carbon-monoxide were used to inhibit mixed function oxidases. Tetraethylpyrophosphate inhibited esterase and trichloropropene-oxide inhibited epoxide-hydrolase. Potassium cyanide or rotenone was used to block the mitochondrial electron transport. The study demonstrated that covalent binding of cismethrin, cypermethrin, and deltamethrin was dependent on pyrethroid concentration. Inhibition of esterases and mitochondrial respiration only slightly altered the covalent binding level. Inhibition of cytochrome p450 and mixed function oxidases reduced the covalent binding, making it almost nonexistent. The covalent binding was decreased by 50% through an 80% inhibition of epoxide-hydrolase. In vitro, the comparison of data between alcohol and acid labeling of the same pyrethroid suggested that the whole molecule was bound to proteins in an activation process, perhaps epoxidation, and that hydrolysis could only occur afterwards. The role of cytochrome p450 dependent monooxygenases in the covalent binding process was stressed.
PMID:2764708 Catinot R et al; Archives of Toxicology 63 (3): 214-20 (1989)
Interaction with sodium channels is not the only mechanism of action proposed for the pyrethroids. Their effects on the CNS have led various workers to suggest actions via antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, or actions on calcium ions. Since neurotransmitter specific pharmacological agents offer only poor or partial protection against poisoning, it is unlikely that one of these effects represents the primary mechanism of action of the pyrethroids, & most neurotransmitter release is secondary to incr sodium entry. /Pyrethroids/
Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 2. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 588
For more Mechanism of Action (Complete) data for CYPERMETHRIN (12 total), please visit the HSDB record page.
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