Permethrin

Permethrin
Two-dimensional chemical structure of permethrin
Three-dimensional chemical structure of permethrin
Clinical data
Trade namesNix, Rid, Elimite, others
AHFS/Drugs.comMonograph
License data
Routes of
administration		topical
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismInsects 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.[2]
Identifiers
  • (±)-3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.052.771 Edit this at Wikidata
Chemical and physical data
FormulaC21H20Cl2O3
Molar mass391.29 g·mol−1
3D model (JSmol)
Density1.19 g/cm3, solid g/cm3
Melting point34 °C (93 °F)
Boiling point200 °C (392 °F)
Solubility in water5.5 x 10−3 ppm, 0.2 [3] mg/mL (25°C)
  • Cl/C(Cl)=C/C3C(C(=O)OCc2cccc(Oc1ccccc1)c2)C3(C)C
  • InChI=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
  • Key:RLLPVAHGXHCWKJ-UHFFFAOYSA-N

Permethrin is a medication and an insecticide.[4][5] As a medication, it is used to treat scabies and lice.[6] It is applied to the skin as a cream or lotion.[4] As an insecticide, it can be sprayed onto outer clothing or mosquito nets to kill the insects that touch them.[5][7]

Side effects include rash and irritation at the area of use.[6] Use during pregnancy appears to be safe.[4] It is approved for use on and around people over the age of two months.[4] Permethrin is in the pyrethroid family of medications.[4] It works by disrupting the function of the neurons of lice and scabies mites.[4]

Permethrin was discovered in 1973.[8] It is on the World Health Organization's List of Essential Medicines.[9] In 2021, it was the 339th most commonly prescribed medication in the United States, with more than 100,000 prescriptions.[10]

  1. ^ "Permethrin Product Information". Health Canada. Retrieved 19 June 2024.
  2. ^ Cite error: The named reference PermGen was invoked but never defined (see the help page).
  3. ^ Metcalf RL, Horowitz AR (19 November 2014). "Insect Control, 2. Individual Insecticides". Ullmann's Encyclopedia of Industrial Chemistry: 1–94. doi:10.1002/14356007.s14_s01. ISBN 978-3-527-30673-2.
  4. ^ a b c d e f "Permethrin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  5. ^ a b Keystone JS, Kozarsky PE, Freedman DO, Connor BA (2013). Travel Medicine. Elsevier Health Sciences. p. 58. ISBN 978-1-4557-1076-8. Archived from the original on 20 December 2016.
  6. ^ a b World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 213. hdl:10665/44053. ISBN 978-92-4-154765-9.
  7. ^ "Repellent-Treated Clothing". United States Environmental Protection Agency. 15 July 2013. Retrieved 28 May 2023.
  8. ^ Zweig G, Sherma J (2013). Synthetic Pyrethroids and Other Pesticides: Analytical Methods for Pesticides and Plant Growth Regulators. Academic Press. p. 104. ISBN 978-1-4832-2090-1. Archived from the original on 20 December 2016.
  9. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  10. ^ "Permethrin - Drug Usage Statistics". ClinCalc. Archived from the original on 26 July 2020. Retrieved 14 January 2024.