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 1410
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 1410
Voltage-sensitive sodium channel 7 Target ID: CHEMBL2362985 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25390654	Inhibitor 8228

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 8360	ELIMITE Approved Use ELIMITE (permethrin) 5% Cream is indicated for the treatment of infestation with Sarcoptesscabiei (scabies). Launch Date 6.2000641E11
Head lice infestation 5 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9b44bf94-62c9-49d8-97ec-cf475824eb35	Curative	Approved 8360	NIX Approved Use To treat head lice. Launch Date 6.3391682E11
Pediculosis 9 Sources: https://www.drugs.com/monograph/permethrin.html	Curative	Approved 8360	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 5.12611189E11
Scabies 9 Sources: https://www.drugs.com/monograph/permethrin.html	Curative	Approved 8360	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 5.12611189E11

C_max

Value	Dose	Analyte	Population
49.46 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768	460 mg/kg single, oral dose: 460 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	PERMETHRIN plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029	10 mg/kg bw single, oral dose: 10 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	PERMETHRIN serum	Gallus gallus domesticus population: HEALTHY 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
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

AUC

Value	Dose	Analyte	Population
159 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768	46 mg/kg single, intravenous dose: 46 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PERMETHRIN plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED
965 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768	460 mg/kg single, oral dose: 460 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	PERMETHRIN plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.95 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029	10 mg/kg bw single, oral dose: 10 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	PERMETHRIN serum	Gallus gallus domesticus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
16.45 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029	10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	PERMETHRIN serum	Gallus gallus domesticus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
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	Analyte	Population
8.67 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768	46 mg/kg single, intravenous dose: 46 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PERMETHRIN plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED
12.37 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768	460 mg/kg single, oral dose: 460 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	PERMETHRIN plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.54 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029	10 mg/kg bw single, oral dose: 10 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	PERMETHRIN serum	Gallus gallus domesticus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
4.73 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029	10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	PERMETHRIN serum	Gallus gallus domesticus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
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 Condition: pediculosis 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 Condition: scabies 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 Condition: crusted scabies 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 Condition: pediculosis 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 Condition: scabies Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/31985943/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1709	substrate 1010	substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B6 799 P-gp 1437	CYP2B6 660 CYP1A2 1032 CYP2C8 688 CYP2C19 985 CYP3A5 391 CYP2A6 523 CYP2E1 648 CYP3A7 110 CYP4A11 102 CES1 22 CES2 28 P-gp 1527

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1626	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/24014652/	no
CYP2B6 985	inhibitor 3240 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=052645531	yes

Drug as victim

Target	Modality	Activity
CYP1A2 1032	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2C8 688	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2C9 1010	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2D6 1193	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP3A5 391	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2A6 523	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
CYP2E1 648	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
CYP3A7 110	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
CYP4A11 102	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
P-gp 1527	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/24014652/	yes [Km 2.8 uM]
CES1 22	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	yes
CES2 28	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	yes
CYP2B6 660	substrate 3326 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=052645531	yes
CYP2C19 985	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	yes
CYP3A4 1709	substrate 3326 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
MolPort	MolPort-003-933-021	https://www.molport.com/shop/molecule-link/MolPort-003-933-021
eMolecules	508544	https://www.emolecules.com/cgi-bin/more?vid=508544

PubMed

Title	Date	PubMed
Constitutive androstane receptor (CAR) as a potential sensing biomarker of persistent organic pollutants (POPs) in aquatic mammal: molecular characterization, expression level, and ligand profiling in Baikal seal (Pusa sibirica).	2006 Nov	16929008
Permethrin may disrupt testosterone biosynthesis via mitochondrial membrane damage of Leydig cells in adult male mouse.	2007 Aug	17463061
Pesticide use and chronic bronchitis among farmers in the Agricultural Health Study.	2007 Dec	17975796
Comparative effect of topical application of lindane and permethrin on oxidative stress parameters in adult scabies patients.	2007 Nov	17884035
Pyrethroids: cytotoxicity and induction of CYP isoforms in human hepatocytes.	2008	19326768
Pesticides and atopic and nonatopic asthma among farm women in the Agricultural Health Study.	2008 Jan 1	17932376
Evaluation of androgen receptor transcriptional activities of some pesticides in vitro.	2008 Jan 14	17980950
Induction of hepatic estrogen-responsive gene transcription by permethrin enantiomers in male adult zebrafish.	2008 Jun 23	18499281
Permethrin may induce adult male mouse reproductive toxicity due to cis isomer not trans isomer.	2008 Jun 27	18455858
High-resolution melt analysis for the detection of a mutation associated with permethrin resistance in a population of scabies mites.	2008 Mar	18380658
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
Cross-induction of detoxification genes by environmental xenobiotics and insecticides in the mosquito Aedes aegypti: impact on larval tolerance to chemical insecticides.	2008 May	18405832
Transcriptional response of rat frontal cortex following acute in vivo exposure to the pyrethroid insecticides permethrin and deltamethrin.	2008 Nov 18	19017407
The effect of insecticide synergists on the response of scabies mites to pyrethroid acaricides.	2009	19125173
Effect of permethrin insecticide on rat polymorphonuclear neutrophils.	2009 Dec 10	19772857
Human carboxylesterases HCE1 and HCE2: ontogenic expression, inter-individual variability and differential hydrolysis of oseltamivir, aspirin, deltamethrin and permethrin.	2009 Jan 15	18983829
Enantioselective induction of estrogen-responsive gene expression by permethrin enantiomers in embryo-larval zebrafish.	2009 Mar	19095286
Pyrethroid insecticides: isoform-dependent hydrolysis, induction of cytochrome P450 3A4 and evidence on the involvement of the pregnane X receptor.	2009 May 15	19249324
The inducibility of human cytochrome P450 1A by environmental-relevant xenobiotics in the human hepatoma derived cell line HepG2.	2009 Nov	21784029
Comparative functional observational battery study of twelve commercial pyrethroid insecticides in male rats following acute oral exposure.	2009 Nov	19748519
Evidence for dose-additive effects of pyrethroids on motor activity in rats.	2009 Oct	20019907
Recent rapid rise of a permethrin knock down resistance allele in Aedes aegypti in México.	2009 Oct 13	19829709
Rhinitis associated with pesticide use among private pesticide applicators in the agricultural health study.	2010	20818537
Estrogenic pyrethroid pesticides regulate expression of estrogen receptor transcripts in mouse Sertoli cells differently from 17beta-estradiol.	2010	20574910
Estrogenic activities of two synthetic pyrethroids and their metabolites.	2010	20397420
Effects of several pyrethroids on hepatic cytochrome P450 activities in rats.	2010 Apr	20009351
Developmental neurotoxicity of pyrethroid insecticides in zebrafish embryos.	2010 Jan	19861644
Assessing hormone receptor activities of pyrethroid insecticides and their metabolites in reporter gene assays.	2010 Jul	20410157
Circadian clock regulates response to pesticides in Drosophila via conserved Pdp1 pathway.	2010 Jun	20348229
Splice variant specific increase in Ca2+/calmodulin-dependent protein kinase 1-gamma mRNA expression in response to acute pyrethroid exposure.	2010 May-Jun	20143453
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
Stereoselective biotransformation of permethrin to estrogenic metabolites in fish.	2010 Oct 18	20836506
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
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

Name

Type

Language

PERMETHRIN

Official 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

PERMETHRIN COMPONENT OF VECTRA 3D

Brand Name

English

(±)-3-PHENOXYBENZYL 3-(2,2-DICHLOROVINYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE

Systematic Name

English

ELIMITE

Brand Name

English

ACTIVYL TICK PLUS

Brand Name

English

PERMETHRIN [INCI]

Common Name

English

PERMETHRIN [IARC]

Common Name

English

NSC-760105

Code

English

PERMETHRIN [ORANGE BOOK]

Common Name

English

COMPONENT OF ACTIVYL TICK PLUS

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