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Revision as of 12:07, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 455823936 of page Phenothrin for the Chem/Drugbox validation project (updated: 'ChEMBL', 'KEGG').  Latest revision as of 03:15, 21 December 2024 edit Mr.choppers (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers69,604 edits Undid revision 1263818712 by PragyaanRover (talk) not betterTag: Undo 
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{{Chembox
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox
| Verifiedfields = changed | Verifiedfields = changed
| UNII_Ref = {{fdacite|changed|FDA}} | Watchedfields = changed
| verifiedrevid = 464200559
| UNII = 707484X33X
| verifiedrevid = 402525596
| ImageFile = Sumithrin-2D-skeletal.png | ImageFile = Sumithrin-2D-skeletal.png
| ImageSize = 200px
| IUPACName = (3-Phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate | IUPACName = (3-Phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
| OtherNames = Sumithrin<br>Phenothrine<br>Phenoxythrin<br>Sumitrin<br>Wellcide<br>Pibutin<br>Anvil<br>Duet<br>Anchimanaito 20S | OtherNames = Sumithrin; Phenothrine; Phenoxythrin; Sumitrin; Wellcide; Pibutin; Anvil; Duet; Anchimanaito 20S
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 26002-80-2
| Abbreviations = | Abbreviations =
| Beilstein = 2160930
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1322884
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4603 | ChemSpiderID = 4603
| DrugBank = DB13717
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| EINECS = 247-404-5
| ChEMBL = <!-- blanked - oldvalue: 1322884 -->
| 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 | 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 | InChIKey = SBNFWQZLDJGRLK-UHFFFAOYAY
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SBNFWQZLDJGRLK-UHFFFAOYSA-N | StdInChIKey = SBNFWQZLDJGRLK-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 26002-80-2
| EINECS = 247-404-5
| PubChem = 4767
| SMILES = O=C(OCc2cccc(Oc1ccccc1)c2)C3C(/C=C(/C)C)C3(C)C | SMILES = O=C(OCc2cccc(Oc1ccccc1)c2)C3C(/C=C(/C)C)C3(C)C
}}
| InChI =
|Section2={{Chembox Properties
| RTECS =
| MeSHName = Phenothrin
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 34916
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = <!-- blanked - oldvalue: D08357 -->
| ATCCode_prefix = P03
| ATCCode_suffix = AC03
| ATC_Supplemental = {{ATCvet|P53|AC03}}
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>23</sub>H<sub>26</sub>O<sub>3</sub> | Formula = C<sub>23</sub>H<sub>26</sub>O<sub>3</sub>
| MolarMass =350.451 g/mol | MolarMass = 350.451 g/mol
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = <25 °C | MeltingPt = <25 °C
| Melting_notes = | MeltingPt_notes =
| BoilingPt = >290 °C | BoilingPt = >290 °C
| Boiling_notes = | BoilingPt_notes =
| Solubility = | Solubility =
| SolubleOther = | SolubleOther =
| Solvent = | Solvent =
| pKa = | pKa =
| pKb = }} | pKb =
}}
| Section7 = {{Chembox Hazards |Section6={{Chembox Pharmacology
| EUClass = | ATCCode_prefix = P03
| EUIndex = | ATCCode_suffix = AC03
| ATC_Supplemental = {{ATCvet|P53|AC03}}
}}
|Section7={{Chembox Hazards
| MainHazards = | MainHazards =
| NFPA-H = | NFPA-H =
| NFPA-F = | NFPA-F =
| NFPA-R = | NFPA-R =
| NFPA-O = | 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>
| RPhrases = {{R36}} {{R38}}
| GHSPictograms = {{GHS07}}{{GHS09}}
| SPhrases =
| GHSSignalWord = Warning
| RSPhrases =
| 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 = | FlashPt =
| Autoignition = | AutoignitionPt =
| ExploLimits = | PEL =
}}
| 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 ] that kills adult ]s and ]s. It has also been used to kill ] in humans. d-Phenothrin is used as a component of aerosol insecticides for domestic use. It is often used with ], an insect growth regulator that interrupts the insect's ] 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 ] (EPA) study found that 0.07 micrograms were enough to kill ]s.<ref name= A /> It is also extremely toxic to aquatic life with a study showing concentrations of 0.03 ] 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 ],<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 ] properties, and was responsible for a small epidemic of ] 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 ] linked sumithrin with ]; the link made by its effect on increasing the expression of a gene responsible for ] 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, ].<ref>, 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>, 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, ]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=] |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==
* ]
* ]
* ]

== References ==
{{reflist}}

==External links==
* – ]
*
*
* {{PPDB|517}}

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

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