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Permethrin is a synthetic pyrethrin derivative acts as a neurotoxin by depolarizing the nerve cell membrane. Permethrin disrupts the sodium channel current by which membrane repolarization is regulated resulting in fatal paralysis of the nerves in the exoskeletal respiratory muscles of susceptible arthropods, including lice and mite. Permethrin is sold under brand names NIx and Elimite to treat pediculosis, scabies and demodicidosis.

Originator

Curator's Comment: Permethrin was allegedly developed by US military to protect soldiers from insects in the jungle. (https://www.oammagazine.com/wp-content/uploads/2016/04/Treating%20your%20Clothes%20with%20Permethrin.pdf).

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ELIMITE

Approved Use

ELIMITE (permethrin) 5% Cream is indicated for the treatment of infestation with Sarcoptesscabiei (scabies).

Launch Date

1989
Curative
NIX

Approved Use

To treat head lice.

Launch Date

1990
Curative
NIX

Approved Use

A synthetic pyrethrin derivative; like natural pyrethrins, acts as a neurotoxin by depolarizing the nerve cell membrane. Disrupts the sodium channel current by which membrane repolarization is regulated resulting in fatal paralysis of the nerves in the exoskeletal respiratory muscles of susceptible arthropods, including lice and mites.

Launch Date

1986
Curative
NIX

Approved Use

A synthetic pyrethrin derivative; like natural pyrethrins, acts as a neurotoxin by depolarizing the nerve cell membrane. Disrupts the sodium channel current by which membrane repolarization is regulated resulting in fatal paralysis of the nerves in the exoskeletal respiratory muscles of susceptible arthropods, including lice and mites.

Launch Date

1986
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
868 ng/mL
143 g single, oral
dose: 143 g
route of administration: Oral
experiment type: SINGLE
co-administered:
PERMETHRIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
253 ng/mL
143 g single, oral
dose: 143 g
route of administration: Oral
experiment type: SINGLE
co-administered:
PERMETHRIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
615 ng/mL
143 g single, oral
dose: 143 g
route of administration: Oral
experiment type: SINGLE
co-administered:
PERMETHRIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2.73 μg × h/mL
143 g single, oral
dose: 143 g
route of administration: Oral
experiment type: SINGLE
co-administered:
PERMETHRIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
6.26 μg × h/mL
143 g single, oral
dose: 143 g
route of administration: Oral
experiment type: SINGLE
co-administered:
PERMETHRIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.08 h
143 g single, oral
dose: 143 g
route of administration: Oral
experiment type: SINGLE
co-administered:
PERMETHRIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
4.82 h
143 g single, oral
dose: 143 g
route of administration: Oral
experiment type: SINGLE
co-administered:
PERMETHRIN serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
PERMETHRIN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 % 1 times / day multiple, topical
Recommended
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Other AEs: Skin and subcutaneous conditions NEC...
Other AEs:
Skin and subcutaneous conditions NEC
Sources:
5 % 1 times / day multiple, topical
Recommended
Dose: 5 %, 1 times / day
Route: topical
Route: multiple
Dose: 5 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Other AEs: Dystonia...
200 ug/kg 1 times / day multiple, oral
Recommended
Dose: 200 ug/kg, 1 times / day
Route: oral
Route: multiple
Dose: 200 ug/kg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
AEs

AEs

AESignificanceDosePopulation
Skin and subcutaneous conditions NEC
1 % 1 times / day multiple, topical
Recommended
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Dystonia
5 % 1 times / day multiple, topical
Recommended
Dose: 5 %, 1 times / day
Route: topical
Route: multiple
Dose: 5 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Radiosynthesis and metabolism in rats of the 1R isomers of the insecticide permethrin.
1976 Mar-Apr
Purification and characterization of trans-permethrin metabolizing microsomal esterases from workers of the eastern subterranean termite, Reticulitermes flavipes (Kollar).
2001 Apr 27
High performance liquid chromatographic determination of diazinon, permethrin, DEET (N, N-diethyl-m-toluamide), and their metabolites in rat plasma and urine.
2001 Jun
Increased ErbB-2 tyrosine kinase activity, MAPK phosphorylation, and cell proliferation in the prostate cancer cell line LNCaP following treatment by select pesticides.
2001 Mar
Simultaneous determination of chlorpyrifos, permethrin, and their metabolites in rat plasma and urine by high-performance liquid chromatography.
2001 May-Jun
A solid phase extraction reversed-phase HPLC method for the simultaneous determination of methoprene, permethrin and selected metabolites in rat plasma and urine.
2001 Nov
Simultaneous determination of malathion, permethrin, DEET (N,N-diethyl-m-toluamide), and their metabolites in rat plasma and urine using high performance liquid chromatography.
2001 Sep
Thermal decomposition and isomerization of cis-permethrin and beta-cypermethrin in the solid phase.
2002 Feb
Neonatal exposure of newborn mice to pyrethroid (permethrin) represses activity-dependent c-fos mRNA expression in cerebellum.
2002 Jul
Comparison of five extraction methods for determination of incurred and added pesticides in dietary composites.
2002 Sep-Oct
Transfer efficiencies of pesticides from household flooring surfaces to foods.
2003 Nov
Inhibition of trans-permethrin hydrolysis in human liver fractions by chloropyrifos oxon and carbaryl.
2004
Microbial transformation of pyrethroid insecticides in aqueous and sediment phases.
2004 Jan
Identification of amino acid residues in the insect sodium channel critical for pyrethroid binding.
2005 Feb
Enantioselectivity in environmental safety of current chiral insecticides.
2005 Jan 18
Lessons learned for the assessment of children's pesticide exposure: critical sampling and analytical issues for future studies.
2005 Oct
Permethrin may disrupt testosterone biosynthesis via mitochondrial membrane damage of Leydig cells in adult male mouse.
2007 Aug
Synergism between cis-permethrin and benzoyl phenyl urea insect growth regulators against Aedes aegypti larvae.
2007 Mar
Efficacy of permethrin cream and oral ivermectin in treatment of scabies.
2007 Oct
Pyrethroids: cytotoxicity and induction of CYP isoforms in human hepatocytes.
2008
Permethrin may induce adult male mouse reproductive toxicity due to cis isomer not trans isomer.
2008 Jun 27
Three mutations identified in the voltage-sensitive sodium channel alpha-subunit gene of permethrin-resistant human head lice reduce the permethrin sensitivity of house fly Vssc1 sodium channels expressed in Xenopus oocytes.
2008 Mar
Mitigation assessment of vegetated drainage ditches for collecting irrigation runoff in California.
2008 Mar-Apr
Neurobehavioral toxicology of pyrethroid insecticides in adult animals: a critical review.
2008 Mar-Apr
Effect of permethrin insecticide on rat polymorphonuclear neutrophils.
2009 Dec 10
In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms.
2009 Jan
Measuring pyrethroids in sediment pore water using matrix-solid phase microextraction.
2009 Jan
The inducibility of human cytochrome P450 1A by environmental-relevant xenobiotics in the human hepatoma derived cell line HepG2.
2009 Nov
Recent rapid rise of a permethrin knock down resistance allele in Aedes aegypti in México.
2009 Oct 13
Isotope dilution gas chromatography/mass spectrometry method for determination of pyrethroids in apple juice.
2010 Mar
Body mass index, agricultural pesticide use, and cancer incidence in the Agricultural Health Study cohort.
2010 Nov
Pesticide use modifies the association between genetic variants on chromosome 8q24 and prostate cancer.
2010 Nov 15
A simple HPLC method for determination of permethrin residues in wine.
2010 Oct
Use of comprehensive screening methods to detect selective human CAR activators.
2011 Dec 15
Fetal exposure to chlordane and permethrin mixtures in relation to inflammatory cytokines and birth outcomes.
2011 Feb 15
Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays.
2011 Feb 27
High frequency of mutations associated with head lice pyrethroid resistance in schoolchildren from Bobigny, France.
2011 Jan
Permethrin treatment of head lice with knockdown resistance-like gene.
2011 Jan 27
Early life permethrin insecticide treatment leads to heart damage in adult rats.
2011 Sep
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.
2011 Sep 14
Activation of a tunicate (Ciona intestinalis) xenobiotic receptor orthologue by both natural toxins and synthetic toxicants.
2012 Feb
The impact of early life permethrin exposure on development of neurodegeneration in adulthood.
2012 Jan
Permethrin exposure during puberty has the potential to enantioselectively induce reproductive toxicity in mice.
2012 Jul
Do pollutants affect insecticide-driven gene selection in mosquitoes? Experimental evidence from transcriptomics.
2012 Jun 15
Inhibition of human MDR1 and BCRP transporter ATPase activity by organochlorine and pyrethroid insecticides.
2013 Feb
Effects of early life permethrin exposure on spatial working memory and on monoamine levels in different brain areas of pre-senescent rats.
2013 Jan 7
Early life permethrin exposure induces long-term brain changes in Nurr1, NF-kB and Nrf-2.
2013 Jun 17
A metabonomic investigation of the effects of 60 days exposure of rats to two types of pyrethroid insecticides.
2013 Nov 25
Pesticide exposure and self-reported incident depression among wives in the Agricultural Health Study.
2013 Oct
Early life permethrin treatment leads to long-term cardiotoxicity.
2013 Oct
Patents

Sample Use Guides

Scabies: Thoroughly massage permethrin 5% cream into the skin from the head to the soles of the feet. Usually 30 grams is sufficient for an average adult. The cream should be removed by washing after 8 to 14 hours. Infants should be treated on the scalp, temple, and forehead. 1 application is generally curative. Lice: completely saturate the hair and scalp with the drug. Begin to apply it behind the ears and at the back of the neck. Leave the shampoo on the hair for 10 minutes, but no longer, rinse with warm water, towel dry hair and comb out tangles. If live lice are seen seven days or more after the first treatment, a second treatment should be given.
Route of Administration: Topical
In Vitro Use Guide
Unknown
Substance Class Mixture
Created
by admin
on Wed Apr 02 15:28:51 GMT 2025
Edited
by admin
on Wed Apr 02 15:28:51 GMT 2025
Record UNII
509F88P9SZ
Record Status FAILED
Record Version
  • Download
Name Type Language
PERMETHRIN
HSDB   INCI   INN   ISO   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN   INCI  
Official Name English
ELIMITE
Preferred Name English
Permethrin [WHO-DD]
Common Name English
PERMETHRIN [ISO]
Common Name English
permethrin [INN]
Common Name English
PERMETHRIN [JAN]
Common Name English
M-PHENOXYBENZYL (±)-3-(2,2-DICHLOROVINYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE
Systematic Name English
PERMETHRIN [HSDB]
Common Name English
MIXTURE OF CIS AND TRANS PERMETHRIN ISOMERS
Common Name English
PERMETHRIN [MI]
Common Name English
PERMETHRIN [VANDF]
Common Name English
CYCLOPROPANECARBOXYLIC ACID, 3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYL-, (3-PHENOXYPHENYL)METHYL ESTER
Common Name English
PERMETHRIN [EMA EPAR VETERINARY]
Common Name English
PERMETHRIN [MART.]
Common Name English
(±)-3-PHENOXYBENZYL 3-(2,2-DICHLOROVINYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE
Systematic Name English
ACTIVYL TICK PLUS
Brand Name English
PERMETHRIN [IARC]
Common Name English
NSC-760105
Code English
PERMETHRIN [ORANGE BOOK]
Common Name English
NIX
Brand Name English
ACTIVYL TICK PLUS COMPONENT PERMETHRIN
Common Name English
VECTRA 3D COMPONENT PERMETHRIN
Brand Name English
PERMETHRIN [USAN]
Common Name English
Classification Tree Code System Code
WHO-VATC QP53AC04
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
WHO-ATC P03AC04
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
WHO-ATC P03AC54
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 13.5
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
EMA VETERINARY ASSESSMENT REPORTS ACTIVYL TICK PLUS (AUTHORIZED)
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
NCI_THESAURUS C29727
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
NDF-RT N0000175847
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
NDF-RT N0000006014
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
EMA VETERINARY ASSESSMENT REPORTS VECTRA 3D [AUTHORIZED]
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
EPA PESTICIDE CODE 109701
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
Code System Code Type Description
DAILYMED
509F88P9SZ
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
PUBCHEM
40326
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
ALANWOOD
permethrin
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
FDA UNII
509F88P9SZ
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
NSC
760105
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
MESH
D026023
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
LACTMED
Permethrin
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
CHEBI
34911
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
SMS_ID
100000091844
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
EPA CompTox
DTXSID8022292
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
DRUG CENTRAL
4152
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
MERCK INDEX
m8564
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C29354
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
INN
5510
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
DRUG BANK
DB04930
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
WIKIPEDIA
PERMETHRIN
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
ChEMBL
CHEMBL1525
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
USAN
U-105
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
HSDB
6790
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
ECHA (EC/EINECS)
258-067-9
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
CAS
52645-53-1
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
EVMPD
SUB09734MIG
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY
RXCUI
33199
Created by admin on Wed Apr 02 15:28:51 GMT 2025 , Edited by admin on Wed Apr 02 15:28:51 GMT 2025
PRIMARY RxNorm
All of the following components must be present:
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Definition References