View source for Phenothrin

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464200559
| ImageFile = Sumithrin-2D-skeletal.png
| IUPACName = (3-Phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
| OtherNames = Sumithrin; Phenothrine; Phenoxythrin; Sumitrin; Wellcide; Pibutin; Anvil; Duet; Anchimanaito 20S
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 26002-80-2
| Abbreviations = 
| Beilstein = 2160930
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1322884
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4603
| DrugBank = DB13717
| EINECS = 247-404-5
| PubChem = 4767
| RTECS =
| MeSHName = Phenothrin
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 34916
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08357
| UNNumber = 3082 2902
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 707484X33X
| 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
| InChIKey = SBNFWQZLDJGRLK-UHFFFAOYAY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SBNFWQZLDJGRLK-UHFFFAOYSA-N
| SMILES = O=C(OCc2cccc(Oc1ccccc1)c2)C3C(/C=C(/C)C)C3(C)C
 }}
|Section2={{Chembox Properties
| Formula = C<sub>23</sub>H<sub>26</sub>O<sub>3</sub>
| MolarMass = 350.451 g/mol
| Appearance =
| Density = 
| MeltingPt = <25 °C
| MeltingPt_notes =
| BoilingPt = >290 °C
| BoilingPt_notes = 
| Solubility = 
| SolubleOther = 
| Solvent = 
| pKa = 
| pKb = 
 }}
|Section6={{Chembox Pharmacology
| ATCCode_prefix = P03
| ATCCode_suffix = AC03
| ATC_Supplemental = {{ATCvet|P53|AC03}}
}}
|Section7={{Chembox Hazards
| MainHazards = 
| NFPA-H = 
| NFPA-F = 
| NFPA-R = 
| NFPA-S =
| Hazards_ref=<ref>{{cite web |title=Phenothrin |url=https://pubchem.ncbi.nlm.nih.gov/compound/4767#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|312|332|410}}
| PPhrases = {{P-phrases|261|264|270|271|273|280|301+312|302+352|304+312|304+340|312|322|330|363|391|501}}
| FlashPt = 
| AutoignitionPt =
| PEL = 
 }}
}}

'''Phenothrin''', also called '''sumithrin''' and '''d-phenothrin''',<ref>{{Cite web
| url = http://npic.orst.edu/ingred/d-phenothrin.html
| title = d-Phenothrin
| website = National Pesticide Information Center
| access-date = 2016-02-29
}}</ref> is a synthetic [[pyrethroid]] that kills adult [[flea]]s and [[tick]]s. It has also been used to kill [[head lice]] in humans. d-Phenothrin is used as a component of aerosol insecticides for domestic use. It is often used with [[methoprene]], an insect growth regulator that interrupts the insect's [[biological life cycle|biological lifecycle]] by killing the eggs. 

== Effects ==
Phenothrin is primarily used to kill fleas and ticks.<ref name=A>{{cite journal |last1=Cox |first1=Caroline |title=Insecticide Factsheet. Sumitherin (D-phenothrin) |journal=Journal of Pesticide Reform |date=2003 |volume=23 |issue=2 |pages=10–14 |url=http://www.pesticide.org/get-the-facts/pesticide-factsheets/factsheets/sumithrin |access-date=2012-08-16|archive-url=https://web.archive.org/web/20120704114748/http://www.pesticide.org/get-the-facts/pesticide-factsheets/factsheets/sumithrin |archive-date=2012-07-04}}</ref> It is also used to kill head lice in humans, but studies conducted in Paris and the United Kingdom have shown widespread resistance to phenothrin.<ref name= A />

It is extremely toxic to bees. A [[U.S. Environmental Protection Agency]] (EPA) study found that 0.07 micrograms were enough to kill [[honey bee]]s.<ref name= A /> It is also extremely toxic to aquatic life with a study showing concentrations of 0.03 [[Parts per billion|ppb]] killing mysid shrimp.<ref name= A/> It has increased risk of liver cancer in rats and mice in long-term exposure, with doses in the 
range of 100 milligrams per kilogram of body weight per day, or above.<ref name= A/>  It is capable of killing [[mosquitoes]],<ref>{{cite web|title=Permethrin, Resmethrin, d-Phenothrin (Sumithrin®): Synthetic Pyrethroids For Mosquito Control|url=https://www.epa.gov/mosquitocontrol/permethrin-resmethrin-d-phenothrin-sumithrinr-synthetic-pyrethroids-mosquito-control|website=US EPA|date=21 February 2013|language=en}}</ref> although remains poisonous to cats and dogs, with seizures and deaths being reported due to poisoning.<ref name= A/> Specific data on concentrations or exposure are lacking.

Phenothrin has been found to possess [[antiandrogen]] properties, and was responsible for a small epidemic of [[gynecomastia]] via isolated environmental exposure.<ref name="BarrosSampaio2012">{{cite journal|last1=Barros|first1=Alfredo Carlos Simões Dornellas de|last2=Sampaio|first2=Marcelo de Castro Moura|title=Gynecomastia: physiopathology, evaluation and treatment|journal=Sao Paulo Medical Journal|volume=130|issue=3|year=2012|pages=187–197|issn=1516-3180|doi=10.1590/S1516-31802012000300009|quote=Reinforcing the evidence suggesting that there is a relationship between chemicals and GM, it is worthwhile mentioning the epidemic onset observed among Haitian refugees in 1981 about four months after arrival in United States detention centers.22 After analyzing all identifiable environmental exposures, it was then found that phenothrin, a multi-insecticide contained in sprays that they had used was the causative agent.23 It is now widely known that phenothrin has antiandrogenic activity.|pmid=22790552|doi-access=free|pmc=10876201}}</ref><ref name="Brody, MD, PhD, FACELoriaux, MD2003">{{cite journal |last1=Brody |first1=Steven A. |last2=Loriaux |first2=D. Lynn |title=Epidemic of gynecomastia among haitian refugees: exposure to an environmental antiandrogen. |journal=Endocrine Practice |date=2003 |volume=9 |issue=5 |pages=370–5 |doi=10.4158/EP.9.5.370 |pmid=14583418|issn=1530-891X}}</ref>

The EPA has not assessed its effect on cancer in humans. However, one study performed by the [[Mount Sinai School of Medicine]] linked sumithrin with [[breast cancer]]; the link made by its effect on increasing the expression of a gene responsible for [[mammary]] tissue proliferation.<ref name= A/>

== EPA action ==
In 2005, the U.S. EPA cancelled permission to use phenothrin in several flea and tick products, at the request of the manufacturer, [[Hartz Mountain Industries]].<ref>[http://www.epa.gov/fedrgstr/EPA-PEST/2005/November/Day-04/p22039.htm Phenothrin and s-Methoprene; Product Cancellation Order], US Environmental Protection Agency {{Webarchive|url=https://web.archive.org/web/20200806075526/https://www.govinfo.gov/app/collection/FR/ |date=2020-08-06 }}</ref><ref>[http://www.epa.gov/fedrgstr/EPA-PEST/2005/November/Day-09/p22256.htm Phenothrin; Amendment to Terminate Use], US Environmental Protection Agency {{Webarchive|url=https://web.archive.org/web/20200609015603/https://www.govinfo.gov/app/collection/FR/ |date=2020-06-09 }}</ref> The products were linked to a range of adverse reactions, including hair loss, salivation, [[tremor]]s, 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.<ref>{{cite web |url=http://hartz.com/Hartz_Products/Dog_Products/Parasite_Protection/Topical_Drops/3270010874_hartz_ultraguard_pro.aspx |title=Hartz.com : Hartz® UltraGuard Pro® Flea & Tick Drops for Dogs and Puppies |access-date=2009-05-20 |url-status=dead |archive-url=https://web.archive.org/web/20090606025644/http://hartz.com/Hartz_Products/Dog_Products/Parasite_Protection/Topical_Drops/3270010874_hartz_ultraguard_pro.aspx |archive-date=2009-06-06 }} See also "dog" in the following EPA ruling: {{cite web |title=Insect Growth Regulators: S-Hydroprene (128966), S-Kinoprene (107502), Methoprene (105401), S-Methoprene (105402) Fact Sheet |publisher=[[U.S. Environmental Protection Agency]] |url=http://www.epa.gov/oppbppd1/biopesticides/ingredients/factsheets/factsheet_igr.htm |url-status=dead |archive-url=https://web.archive.org/web/20090624071746/http://www.epa.gov/oppbppd1/biopesticides/ingredients/factsheets/factsheet_igr.htm |archive-date=2009-06-24 }}</ref>

==See also==
* [[Permethrin]] 
* [[Resmethrin]]
* [[Deltamethrin]]

== References ==
{{reflist}}

==External links==
* [http://npic.orst.edu/ingred/d-phenothrin.html d-Phenothrin general information] – [[National Pesticide Information Center]] 
* [http://npic.orst.edu/factsheets/pyrethrins.pdf Pyrethrins and Pyrethroids Fact Sheet – National Pesticide Information Center]
* [http://extoxnet.orst.edu/pips/pyrethri.htm Pyrethrins and Pyrethroids Pesticide Information Profile – Extension Toxicology Network]
* {{PPDB|517}}

{{Insecticides}}
{{Ectoparasiticides}}
{{Androgen receptor modulators}}
{{Human lice}}

[[Category:Chrysanthemate esters]]
[[Category:Endocrine disruptors]]
[[Category:Nonsteroidal antiandrogens]]
[[Category:Pest control]]
[[Category:(3-phenoxyphenyl)methyl 2,2,3-trimethylcyclopropane-1-carboxylates]]