Structure via PubChem · Public domain (PubChem)
permethrin
Sign in to saveAlso known as (3-Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate, 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid, (3-phenoxyphenyl) methyl ester, Elimite, Nix
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 an insecticide, it can be sprayed onto outer clothing or mosquito nets to kill the insects that touch them.
Key facts
- Drug.image
- Permethrin-2D-skeletal.svg
- Drug.image_class
- skin-invert-image
- Drug.caption
- Two-dimensional chemical structure of permethrin
- Drug.image2
- Permethrin MT 20200909.png
- Drug.image_class2
- bg-transparent
- Drug.caption2
- Three-dimensional chemical structure of permethrin
- Drug.tradename
- Nix, Rid, Elimite, others
- Drug.MedlinePlus
- a698037
- Drug.DailyMedID
- Permethrin
- Drug.routes_of_administration
- Topical
- Drug.ATC_prefix
- P03
- Drug.ATC_suffix
- AC04
- Drug.legal_CA
- OTC
- Drug.legal_UK
- OTC
- Drug.legal_UK_comment
- (1%), Rx (5%)
- Drug.legal_US
- OTC
- Drug.legal_US_comment
- (1% pediculicide), Rx (5% scabicide)
- Drug.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.
via Wikipedia infobox
Chemical data
- Formula
- C21H20Cl2O3
- Molecular weight
- 391.3 g/mol
- IUPAC name
- (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
- SMILES
- CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
- InChIKey
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N
- XLogP
- 6.5
- Polar surface area
- 35.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
5,013 papers- Comparison of sulfur ointment and permethrin treatments in scabies.Dermatologic therapy · 2022
- Permethrin-resistant scabies.Medicina clinica · 2024
- Comparison of topical permethrin 5% vs. benzyl benzoate 25% treatment in scabies: a double-blinded randomized controlled trial.The British journal of dermatology · 2024
- Permethrin and ivermectin for scabies.The New England journal of medicine · 2010
- Pseudoresistance to permethrin in scabies.Journal of infection in developing countries · 2023
via PubMed
~14 min read
Encyclopedic overview
20 sectionsContents
- Uses
- Medical use
- Insect incapacitation
- Insecticide
- Pest control
- Resistance
- Adverse effects
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Chemistry
- Stereochemistry
- Environment
- History
- Brand names
- Other animals
- Cats
- Aquatic organisms
- References
- External links
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 an insecticide, it can be sprayed onto outer clothing or mosquito nets to kill the insects that touch them.
Side effects include rash and irritation where it is applied. Use during pregnancy appears to be safe, and it is approved for use on and around people over the age of two months in the United States. Permethrin is in the pyrethroid family of medications. It works by disrupting the function of the neurons of lice and scabies mites. Permethrin is highly toxic to cats and fish.
Excerpted from Wikipedia’s “permethrin” article, available under the CC BY-SA 4.0 licence.