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Permethrin information


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
  • US DailyMed: Permethrin
Routes of
administration
topical
ATC code
  • P03AC04 (WHO) QP53AC04 (WHO)
Legal status
Legal status
  • CA: ℞-only
  • UK: OTC (1%), Rx (5%)
  • US: OTC (1% pediculicide), Rx (5% scabicide)
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, although not experiencing the full effect of permethrin, are more sensitive to this toxin.[1]
Identifiers
IUPAC name
  • (±)-3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
CAS Number
  • 52645-53-1  checkY
PubChem CID
  • 40326
DrugBank
  • DB04930
ChemSpider
  • 36845
UNII
  • 509F88P9SZ
KEGG
  • C14388
ChEBI
  • CHEBI:34911
ChEMBL
  • ChEMBL1525
CompTox Dashboard (EPA)
  • DTXSID8022292 Edit this at Wikidata
ECHA InfoCard100.052.771 Edit this at Wikidata
Chemical and physical data
FormulaC21H20Cl2O3
Molar mass391.29 g·mol−1
3D model (JSmol)
  • Interactive image
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 [2] mg/mL (25°C)
SMILES
  • Cl/C(Cl)=C/C3C(C(=O)OCc2cccc(Oc1ccccc1)c2)C3(C)C
InChI
  • 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.[3][4] As a medication, it is used to treat scabies and lice.[5] It is applied to the skin as a cream or lotion.[3] As an insecticide, it can be sprayed onto outer clothing or mosquito nets to kill the insects that touch them.[4][6]

Side effects include rash and irritation at the area of use.[5] Use during pregnancy appears to be safe.[3] It is approved for use on and around people over the age of two months.[3] Permethrin is in the pyrethroid family of medications.[3] It works by disrupting the function of the neurons of lice and scabies mites.[3]

Permethrin was discovered in 1973.[7] It is on the World Health Organization's List of Essential Medicines.[8] In 2021, it was the 339th most commonly prescribed medication in the United States, with more than 100,000 prescriptions.[9]

  1. ^ Cite error: The named reference PermGen was invoked but never defined (see the help page).
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ "Repellent-Treated Clothing". United States Environmental Protection Agency. 15 July 2013. Retrieved 28 May 2023.
  7. ^ 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.
  8. ^ 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.
  9. ^ "Permethrin - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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Permethrin

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Permethrin is a medication and an insecticide. As a medication, it is used to treat scabies and lice. It is applied to the skin as a cream or lotion. As...

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Scabies

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available to treat those infected, including oral and topical ivermectin, and permethrin, crotamiton, and lindane creams. Sexual contacts within the last month...

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infections (STIs) are usually performed. First line treatment usually contains permethrin and is available over the counter. Two rounds of treatment at least a...

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Knockdown resistance, also called kdr, describes cases of resistance to diphenylethane (e.g. DDT) and pyrethroid insecticides in insects and other arthropods...

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Dinotefuran

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flea preventive for cats. It is used in combination with pyriproxifen or permethrin. Current studies show dinotefuran is effective at controlling the invasive...

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Pyrethroid

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Flucythrinate Flumethrin Imiprothrin lambda-Cyhalothrin Metofluthrin Permethrin, dichlorovinyl derivative of pyrethrin and most widely used pyrethroid...

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Pyrethrum

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insecticides based on natural pyrethrum (pyrethrins); one common example is permethrin. Pyrethrins are often sold in preparations that also contain the synthetic...

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Acaricide

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mites and ticks are usually treated as a single group. Examples include: Permethrin can be applied as a spray. The effects are not limited to mites: lice...

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Ectoparasiticide

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These drugs are used to kill the parasites that live on the body surface. Permethrin, sulfur, lindane, dicophane, benzyl benzoate, ivermectin and crotamiton...

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tents, backpacks and sleeping bags with 0.5% permethrin solution and hanging them to dry before use. Permethrin is odorless and safe for humans but highly...

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Mosquito net

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addition, insecticides with which the mesh has been treated, such as permethrin, may be harmful to the fish and other aquatic fauna. Mosquito nets treated...

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Mange

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be observed for eight hours after the first monthly treatment. Topical permethrin is also effective in both dogs and humans, but is toxic to cats.[citation...

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Typhus

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scrub is common in the area. Make sure your clothing is treated with permethrin to prevent mite bites. Lastly, make sure to use bug spray to keep mites...

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Deltamethrin

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insecticide, can be used in conjunction with, or as an alternative to, permethrin, cypermethrin and organophosphate-based insecticides, such as malathion...

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Benzyl benzoate

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a medication it is used to treat scabies and lice. For scabies either permethrin or malathion is typically preferred. It is applied to the skin as a lotion...

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ATC code P03

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Phenothrin P03AC04 Permethrin P03AC51 Pyrethrum, combinations P03AC52 Bioallethrin, combinations P03AC53 Phenothrin, combinations P03AC54 Permethrin, combinations...

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Mountain pine beetle

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organisms. Permethrin is easily metabolized in mammalian livers, so is less dangerous to humans. Birds are also practically not affected by permethrin. Negative...

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Propiconazole

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nectarines, plums, prunes and lemons. It is also used in combination with permethrin in formulations of wood preserver. Propiconazole is a mixture of four...

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Head lice infestation

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often preferred due to the low risk of side effects. Pyrethroids such as permethrin have been commonly used; however, they have become less effective due...

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next year to ensure the infestation is under control.[citation needed] Permethrin – A particular synthetic pyrethroid available as aerosol spray. Disadvantages:...

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Infestation can be controlled by application of a residual insecticide (such as permethrin) to infected areas, by professional fumigation, or by replacing infected...

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Chrysanthemum

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and also decompose easily on exposure to light. Pyrethroids such as permethrin are synthetic insecticides based on natural pyrethrum. Despite this, chrysanthemum...

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Treatment of human lice

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include lindane, malathion, carbaryl, pyrethrum, piperonyl butoxide, permethrin, phenothrin, bioallethrin, and spinosad. Many of the pediculicides in...

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Varied carpet beetle

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the behavioural responses of Anthrenus verbasci adults and larvae to permethrin (ec) using a computerized tracking system". Journal of Stored Products...

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scabiei – is most commonly treated with topical permethrin or oral ivermectin. A single application of permethrin is more efficacious than a single treatment...

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