Cypermethrin

Cypermethrin

Names
IUPAC name [Cyano-(3-phenoxyphenyl)methyl]3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
Identifiers
CAS Number	52315-07-8 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:4042 Y
ChEMBL	ChEMBL373204 Y
ChemSpider	2809 Y
ECHA InfoCard	100.052.567
KEGG	D07763 Y
MeSH	Cypermethrin
PubChem	2912
UNII	1TR49121NP Y
InChI InChI=1S/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3 Y Key: KAATUXNTWXVJKI-UHFFFAOYSA-N Y InChI=1/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3 Key: KAATUXNTWXVJKI-UHFFFAOYAW
SMILES Cl/C(Cl)=C/C3C(C(=O)OC(C#N)c2cccc(Oc1ccccc1)c2)C3(C)C
Properties
Chemical formula	C22H19Cl2NO3
Molar mass	416.30 g/mol
Pharmacology
ATC code	P03BA02 (WHO) QP53AC08 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Cypermethrin is a synthetic pyrethroid used as an insecticide in large-scale commercial agricultural applications as well as in consumer products for domestic purposes. It behaves as a fast-acting neurotoxin in insects. It is easily degraded on soil and plants but can be effective for weeks when applied to indoor inert surfaces. Exposure to sunlight, water and oxygen will accelerate its decomposition. Cypermethrin is highly toxic to fish, bees and aquatic insects, according to the National Pesticides Telecommunications Network (NPTN). It is found in many household ant and cockroach killers, including Raid and ant chalk.

Cypermethrin is used in agriculture to control ectoparasites which infest cattle, sheep, and poultry. In veterinary medicine, it is effective at controlling ticks on dogs.

Cypermethrin is a moderately toxic through skin contact or ingestion. Excessive exposure can cause nausea, headache, muscle weakness, salivation, shortness of breath and seizures. In humans, cypermethrin is deactivated by enzymatic hydrolysis to several carboxylic acid metabolites, which are eliminated in the urine. Worker exposure to the chemical can be monitored by measurement of the urinary metabolites, while severe overdosage may be confirmed by quantitation of cypermethrin in blood or plasma.

Cypermethrin is very toxic to cats which cannot tolerate the therapeutic doses for dogs. This is associated with glucuronidase deficiency in cats, the enzyme responsible for metabolizing cypermethrin. As a consequence, cypermethrin remains much longer in the cat's organism than in dogs or other mammals and can be fatal in large doses.

In male rats cypermethrin was shown to exhibit a toxic effect on the reproductive system. After 15 days of continual dosing, both androgen receptor levels and serum testosterone levels were significantly reduced. These data suggested that cypermethrin can induce impairments of the structure of seminiferous tubules and spermatogenesis in male rats at high doses.