Phenothrin

Phenothrin

Names
IUPAC name (3-Phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
Other names Sumithrin Phenothrine Phenoxythrin Sumitrin Wellcide Pibutin Anvil Duet Anchimanaito 20S
Identifiers
CAS Number	26002-80-2 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:34916 Y
ChEMBL	ChEMBL1322884 N
ChemSpider	4603 Y
ECHA InfoCard	100.043.079
EC Number	247-404-5
KEGG	D08357 N
MeSH	Phenothrin
PubChem CID	4767
UNII	707484X33X Y
CompTox Dashboard (EPA)	DTXSID7032688
InChI InChI=1S/C23H26O3/c1-16(2)13-20-21(23(20,3)4)22(24)25-15-17-9-8-12-19(14-17)26-18-10-6-5-7-11-18/h5-14,20-21H,15H2,1-4H3 Y Key: SBNFWQZLDJGRLK-UHFFFAOYSA-N Y InChI=1/C23H26O3/c1-16(2)13-20-21(23(20,3)4)22(24)25-15-17-9-8-12-19(14-17)26-18-10-6-5-7-11-18/h5-14,20-21H,15H2,1-4H3 Key: SBNFWQZLDJGRLK-UHFFFAOYAY
SMILES O=C(OCc2cccc(Oc1ccccc1)c2)C3C(/C=C(/C)C)C3(C)C
Properties
Chemical formula	C23H26O3
Molar mass	350.451 g/mol
Melting point	<25 °C
Boiling point	>290 °C
Pharmacology
ATC code	P03AC03 (WHO) QP53AC03 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Phenothrin, also called sumithrin and d-phenothrin, is a synthetic pyrethroid that kills adult fleas and ticks. It has also been used to kill head lice in humans. d-Phenothrin is used as a component of aerosol insecticides for domestic use. Phenothrin is often used with methoprene, an insect growth regulator that interrupts the insect's biological life cycle by killing the eggs. Phenothrin is the active agent in the branded product Raid Fly & Wasp Killer.

Effects

Phenothrin is primarily used to kill fleas and ticks. It is also used to kill head lice in humans, but studies conducted in Paris, France and the United Kingdom have shown widespread resistance to phenothrin.

It is extremely toxic to bees. A U.S. Environmental Protection Agency (EPA) study found that 0.07 micrograms was enough to kill honey bees. It is also extremely toxic to aquatic life with a study showing concentrations of 0.03 ppb killing mysid shrimp. It has increased risk of liver cancer in rats and mice in long term exposure. It is capable of killing mosquitoes, although remains poisonous to cats and dogs, with seizures and deaths being reported due to poisoning. Specific data on concentrations or exposure is lacking.

The EPA has not assessed its effect on cancer in humans. However, one study performed by the Mt. Sinai School of Medicine links sumithrin with breast cancer; the link made by sumithrin's effect on increasing the expression of a gene responsible for mammary tissue proliferation.

EPA action

In 2005, the U.S. EPA canceled permission to use phenothrin in several flea and tick products, at the request of the manufacturer, Hartz Mountain Industries. The products were linked to a range of adverse reactions, including hair loss, salivation, tremors, and numerous deaths in cats and kittens. In the short term, the agreement called for new warning labels on the products.

As of March 31, 2006, the sale and distribution of Hartz's phenothrin-containing flea and tick products for cats has been terminated. However, EPA's product cancellation order did not apply to Hartz flea and tick products for dogs, and Hartz continues to produce many of its flea and tick products for dogs.

See also

• Permethrin and Resmethrin, other synthetic pyrethroids

External links

• d-Phenothrin general information - National Pesticide Information Center
• Pyrethrins and Pyrethroids Fact Sheet - National Pesticide Information Center
• Pyrethrins and Pyrethroids Pesticide Information Profile - Extension Toxicology Network
• Phenothrin in the Pesticide Properties DataBase (PPDB)