PERMETHRIN

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c6c509bb-658e-46eb-a844-8323ecd115dehttps://www.drugs.com/monograph/permethrin.html

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-sensitive sodium channel 7 Target ID: CHEMBL2362985 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c6c509bb-658e-46eb-a844-8323ecd115de	Activator 1447
Voltage-sensitive sodium channel alpha-subunit 5 Target ID: CHEMBL2362984 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c6c509bb-658e-46eb-a844-8323ecd115de	Activator 1447
Voltage-sensitive sodium channel 7 Target ID: CHEMBL2362985 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25390654	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Scabies 9 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c6c509bb-658e-46eb-a844-8323ecd115de	Curative	Approved 8583	ELIMITE Approved Use ELIMITE (permethrin) 5% Cream is indicated for the treatment of infestation with Sarcoptesscabiei (scabies). Launch Date 1989
Head lice infestation 5 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9b44bf94-62c9-49d8-97ec-cf475824eb35	Curative	Approved 8583	NIX Approved Use To treat head lice. Launch Date 1990
Pediculosis 9 Sources: https://www.drugs.com/monograph/permethrin.html	Curative	Approved 8583	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
Scabies 9 Sources: https://www.drugs.com/monograph/permethrin.html	Curative	Approved 8583	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

C_max

Value	Dose	Analyte	Population
868 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/9541045	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/9541045	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/9541045	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

Value	Dose	Co-administered	Analyte	Population
2.73 μg × h/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/9541045	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/9541045	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.08 h REVIEW https://pubmed.ncbi.nlm.nih.gov/9541045	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 REVIEW https://pubmed.ncbi.nlm.nih.gov/9541045	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31248885			PERMETHRIN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
1 % 1 times / day multiple, topical Recommended Dose: 1 %, 1 times / day Route: topical Route: multiple Dose: 1 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31985943/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/31985943/	Other AEs: Skin and subcutaneous conditions NEC... Other AEs: Skin and subcutaneous conditions NEC Sources: https://pubmed.ncbi.nlm.nih.gov/31985943/
5 % 1 times / day multiple, topical Recommended Dose: 5 %, 1 times / day Route: topical Route: multiple Dose: 5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31985943/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/31985943/	Other AEs: Dystonia... Other AEs: Dystonia Sources: https://pubmed.ncbi.nlm.nih.gov/31985943/
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: https://pubmed.ncbi.nlm.nih.gov/31985943/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/31985943/	Sources: https://pubmed.ncbi.nlm.nih.gov/31985943/

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/31985943/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/31985943/
Dystonia		5 % 1 times / day multiple, topical Recommended Dose: 5 %, 1 times / day Route: topical Route: multiple Dose: 5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31985943/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/31985943/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B6 926 P-gp 1741	CYP2B6 776 CYP1A2 1197 CYP2C8 810 CYP2C19 1119 CYP3A5 446 CYP2A6 626 CYP2E1 729 CYP3A7 109 CYP4A11 137 CES1 45 CES2 33 P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/24014652/	no
CYP2B6 1160	inhibitor 4027 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=052645531	yes

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
CYP3A7 109	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
CYP4A11 137	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24014652/	yes [Km 2.8 uM]
CES1 45	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	yes
CES2 33	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	yes
CYP2B6 776	substrate 4014 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=052645531	yes
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	yes
CYP3A4 1946	substrate 4014 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=052645531	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:34911	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:34911
ChemicalBook	CB8312237	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8312237
eMolecules	508544	https://www.emolecules.com/cgi-bin/more?vid=508544
MolPort	MolPort-003-933-021	https://www.molport.com/shop/molecule-link/MolPort-003-933-021

PubMed

Title	Date	PubMed
Radiosynthesis and metabolism in rats of the 1R isomers of the insecticide permethrin.	1976 Mar-Apr	1254806
Purification and characterization of trans-permethrin metabolizing microsomal esterases from workers of the eastern subterranean termite, Reticulitermes flavipes (Kollar).	2001 Apr 27	11267909
High performance liquid chromatographic determination of diazinon, permethrin, DEET (N, N-diethyl-m-toluamide), and their metabolites in rat plasma and urine.	2001 Jun	11495064
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	11222871
Simultaneous determination of chlorpyrifos, permethrin, and their metabolites in rat plasma and urine by high-performance liquid chromatography.	2001 May-Jun	11386641
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	11746243
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	11470206
Thermal decomposition and isomerization of cis-permethrin and beta-cypermethrin in the solid phase.	2002 Feb	11852644
Neonatal exposure of newborn mice to pyrethroid (permethrin) represses activity-dependent c-fos mRNA expression in cerebellum.	2002 Jul	12111003
Comparison of five extraction methods for determination of incurred and added pesticides in dietary composites.	2002 Sep-Oct	12374417
Transfer efficiencies of pesticides from household flooring surfaces to foods.	2003 Nov	14603346
Inhibition of trans-permethrin hydrolysis in human liver fractions by chloropyrifos oxon and carbaryl.	2004	15663293
Microbial transformation of pyrethroid insecticides in aqueous and sediment phases.	2004 Jan	14768859
Identification of amino acid residues in the insect sodium channel critical for pyrethroid binding.	2005 Feb	15525757
Enantioselectivity in environmental safety of current chiral insecticides.	2005 Jan 18	15632216
Lessons learned for the assessment of children's pesticide exposure: critical sampling and analytical issues for future studies.	2005 Oct	16203262
Permethrin may disrupt testosterone biosynthesis via mitochondrial membrane damage of Leydig cells in adult male mouse.	2007 Aug	17463061
Synergism between cis-permethrin and benzoyl phenyl urea insect growth regulators against Aedes aegypti larvae.	2007 Mar	17536364
Efficacy of permethrin cream and oral ivermectin in treatment of scabies.	2007 Oct	17978449
Pyrethroids: cytotoxicity and induction of CYP isoforms in human hepatocytes.	2008	19326768
Permethrin may induce adult male mouse reproductive toxicity due to cis isomer not trans isomer.	2008 Jun 27	18455858
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	18252244
Mitigation assessment of vegetated drainage ditches for collecting irrigation runoff in California.	2008 Mar-Apr	18268312
Neurobehavioral toxicology of pyrethroid insecticides in adult animals: a critical review.	2008 Mar-Apr	18206347
Effect of permethrin insecticide on rat polymorphonuclear neutrophils.	2009 Dec 10	19772857
In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms.	2009 Jan	18948380
Measuring pyrethroids in sediment pore water using matrix-solid phase microextraction.	2009 Jan	18712946
The inducibility of human cytochrome P450 1A by environmental-relevant xenobiotics in the human hepatoma derived cell line HepG2.	2009 Nov	21784029
Recent rapid rise of a permethrin knock down resistance allele in Aedes aegypti in México.	2009 Oct 13	19829709
Isotope dilution gas chromatography/mass spectrometry method for determination of pyrethroids in apple juice.	2010 Mar	20101497
Body mass index, agricultural pesticide use, and cancer incidence in the Agricultural Health Study cohort.	2010 Nov	20730623
Pesticide use modifies the association between genetic variants on chromosome 8q24 and prostate cancer.	2010 Nov 15	20978189
A simple HPLC method for determination of permethrin residues in wine.	2010 Oct	20845181
Use of comprehensive screening methods to detect selective human CAR activators.	2011 Dec 15	21924250
Fetal exposure to chlordane and permethrin mixtures in relation to inflammatory cytokines and birth outcomes.	2011 Feb 15	21235202
Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays.	2011 Feb 27	21115097
High frequency of mutations associated with head lice pyrethroid resistance in schoolchildren from Bobigny, France.	2011 Jan	21337951
Permethrin treatment of head lice with knockdown resistance-like gene.	2011 Jan 27	21268748
Early life permethrin insecticide treatment leads to heart damage in adult rats.	2011 Sep	21616133
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.	2011 Sep 14	21786822
Activation of a tunicate (Ciona intestinalis) xenobiotic receptor orthologue by both natural toxins and synthetic toxicants.	2012 Feb	22206814
The impact of early life permethrin exposure on development of neurodegeneration in adulthood.	2012 Jan	22056222
Permethrin exposure during puberty has the potential to enantioselectively induce reproductive toxicity in mice.	2012 Jul	21745691
Do pollutants affect insecticide-driven gene selection in mosquitoes? Experimental evidence from transcriptomics.	2012 Jun 15	22406618
Inhibition of human MDR1 and BCRP transporter ATPase activity by organochlorine and pyrethroid insecticides.	2013 Feb	23169446
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	23174539
Early life permethrin exposure induces long-term brain changes in Nurr1, NF-kB and Nrf-2.	2013 Jun 17	23566817
A metabonomic investigation of the effects of 60 days exposure of rats to two types of pyrethroid insecticides.	2013 Nov 25	24121187
Pesticide exposure and self-reported incident depression among wives in the Agricultural Health Study.	2013 Oct	23916637
Early life permethrin treatment leads to long-term cardiotoxicity.	2013 Oct	23806482

Patents

Sample Use Guides

In Vivo Use Guide

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

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Name

Type

Language

PERMETHRIN

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