Editing Permethrin (section)

{{Short description|Medication and insecticide}}
{{Use dmy dates|date=March 2024}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| image             = Permethrin-2D-skeletal.png
| image_class       = skin-invert-image
| alt               =
| caption           = Two-dimensional chemical structure of permethrin
| image2             = Permethrin MT 20200909.png
| image_class2       = bg-transparent
| alt2               =
| caption2           = Three-dimensional chemical structure of permethrin

<!-- Clinical data -->
| pronounce         = 
| tradename         = Nix, Rid, Elimite, others
| Drugs.com         = {{Drugs.com|monograph|permethrin}}
| MedlinePlus       = a698037
| DailyMedID        = Permethrin
| pregnancy_AU      = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU_comment = 
| pregnancy_category=
| routes_of_administration = [[topical administration|Topical]]
| class             = 
| ATC_prefix        = P03
| ATC_suffix        = AC04
| ATC_supplemental  = {{ATCvet|P53|AC04}}

<!-- Legal status -->
| legal_AU          = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| legal_AU_comment  = 
| legal_BR          = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C5, D1, D2, E, F1, F2, F3, F4 -->
| legal_BR_comment  = 
| legal_CA          = OTC
| legal_CA_comment  = <ref>{{cite web |title=Nix Product Information |url=https://health-products.canada.ca/dpd-bdpp/info?lang=eng&code=37239 |website=[[Health Canada]]|access-date=19 June 2024}}</ref>
| legal_DE          = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment  = 
| legal_NZ          = <!-- Class A, B, C -->
| legal_NZ_comment  = 
| legal_UK = OTC 
| legal_UK_comment = (1%), Rx (5%)
| legal_US = OTC 
| legal_US_comment = (1% [[pediculicide]]),<ref>{{cite web | title=Good Sense Lice Killing Creme Rinse- permethrin lotion | website=DailyMed | date=21 November 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=056fb377-34dd-4d33-83d7-c895b105f574 | access-date=29 December 2024}}</ref> Rx (5% [[scabicide]])<ref name="Elimite FDA label">{{cite web | title=Elimite- permethrin cream | website=DailyMed | date=24 January 2024 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=443c0446-ccba-4f52-83ed-4c3163f35807 | access-date=29 December 2024}}</ref>
| legal_EU          = 
| legal_EU_comment  = 
| legal_UN          = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment  = 
| legal_status      = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->
| bioavailability   =
| protein_bound     =
| metabolism        = Insects are more affected by permethrin than humans or dogs because they are unable to metabolise the toxins as quickly as humans and dogs. Cats are more sensitive to this toxin.<ref name=PermGen/>
| metabolites       =
| onset             =
| elimination_half-life =
| duration_of_action =
| excretion         =

<!-- Identifiers -->
| CAS_number        = 52645-53-1
| CAS_supplemental  = {{cascite|correct|CAS}}
| PubChem           = 40326
| IUPHAR_ligand     =
| DrugBank          = DB04930
| ChemSpiderID      = 36845
| UNII              = 509F88P9SZ
| KEGG              = C14388
| ChEBI             = 34911
| ChEMBL            = 1525
| NIAID_ChemDB      =
| PDB_ligand        = 
| synonyms          =

<!-- Chemical and physical data -->
| IUPAC_name        = (±)-3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
| C=21
| H=20
| Cl=2
| O=3
| SMILES            = Cl/C(Cl)=C/C3C(C(=O)OCc2cccc(Oc1ccccc1)c2)C3(C)C
| StdInChI          = 1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3
| StdInChI_comment  =
| StdInChIKey       = RLLPVAHGXHCWKJ-UHFFFAOYSA-N
| density           = 1.19 g/cm<sup>3</sup>, solid
| density_notes     =
| melting_point     = 34
| melting_high      =
| melting_notes     =
| boiling_point     = 200
| boiling_notes     =
| solubility        = 5.5 x 10<sup>−3</sup> [[Parts per million|ppm]], 0.2 <ref>{{cite journal | vauthors = Metcalf RL, Horowitz AR |title=Insect Control, 2. Individual Insecticides |journal=Ullmann's Encyclopedia of Industrial Chemistry |date=19 November 2014 |pages=1–94 |doi=10.1002/14356007.s14_s01 |isbn=978-3-527-30673-2 }}</ref>
| sol_units  = &nbsp;mg/mL (25°C)
| specific_rotation =
}}

<!-- Definition and uses -->
'''Permethrin''' is a medication and an [[insecticide]].<ref name=AHFS2016 /><ref name=Key2013>{{cite book| vauthors = Keystone JS, Kozarsky PE, Freedman DO, Connor BA |title=Travel Medicine|date=2013|publisher=Elsevier Health Sciences|isbn=978-1-4557-1076-8|page=58|url=https://books.google.com/books?id=hSf30j2YFSMC&pg=PA58|language=en|url-status=live|archive-url=https://web.archive.org/web/20161220155051/https://books.google.ca/books?id=hSf30j2YFSMC&pg=PA58|archive-date=20 December 2016}}</ref> As a medication, it is used to treat [[scabies]] and [[lice]].<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 978-92-4-154765-9 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | page = 213 }}</ref> It is applied to the skin as a cream or lotion.<ref name=AHFS2016>{{cite web|title=Permethrin|url=https://www.drugs.com/monograph/permethrin.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161221013040/https://www.drugs.com/monograph/permethrin.html|archive-date=21 December 2016}}</ref> As an insecticide, it can be sprayed onto outer clothing or [[mosquito nets]] to kill the insects that touch them.<ref name=Key2013 /><ref name="usepa">{{cite web |title=Repellent-Treated Clothing |date=15 July 2013 |url=https://www.epa.gov/insect-repellents/repellent-treated-clothing |publisher=United States Environmental Protection Agency |access-date=28 May 2023}}</ref>

<!-- Side effects and mechanism -->
Side effects include rash and irritation where it is [[Topical medication|applied]].<ref name=WHO2008 /> Use during [[pregnancy]] appears to be safe, and it is approved for use on and around people over the age of two months.<ref name=AHFS2016 /> Permethrin is in the [[pyrethroid]] family of medications.<ref name=AHFS2016 /> It works by disrupting the function of the [[neuron]]s of lice and scabies mites.<ref name=AHFS2016 />

<!-- Society and culture -->
Permethrin was discovered in 1972.<ref name=":0" /> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref> In 2022, it was the 351st most commonly prescribed medication in the United States, with more than 40,000 prescriptions.<ref>{{cite web | title = Permethrin Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Permethrin | access-date = 30 August 2024 }}</ref>