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 1430
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 1430
Voltage-sensitive sodium channel 7 Target ID: CHEMBL2362985 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25390654	Inhibitor 8297

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 8429	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 8429	NIX Approved Use To treat head lice. Launch Date 1990
Pediculosis 9 Sources: https://www.drugs.com/monograph/permethrin.html	Curative	Approved 8429	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 8429	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
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 1737	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B6 810 P-gp 1461	CYP2B6 664 CYP1A2 1054 CYP2C8 693 CYP2C19 991 CYP3A5 395 CYP2A6 543 CYP2E1 667 CYP3A7 110 CYP4A11 119 CES1 22 CES2 28 P-gp 1537

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/24014652/	no
CYP2B6 1001	inhibitor 3277 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=052645531	yes

Drug as victim

Target	Modality	Activity
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP3A5 395	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
CYP3A7 110	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
CYP4A11 119	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/24014652/	yes [Km 2.8 uM]
CES1 22	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	yes
CES2 28	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	yes
CYP2B6 664	substrate 3367 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=052645531	yes
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	yes
CYP3A4 1737	substrate 3367 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
Radiosynthesis and metabolism in rats of the 1R isomers of the insecticide permethrin.	1976 Mar-Apr	1254806
Purification and preliminary characterization of permethrinase from a pyrethroid-transforming strain of Bacillus cereus.	1993 Jul	8357241
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
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
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
[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals].	2004 Apr	15272608
Determination of solid-liquid partition coefficients (K(d)) for diazinon, propetamphos and cis-permethrin: implications for sheep dip disposal.	2004 Aug 15	15262167
Identification, expression, and purification of a pyrethroid-hydrolyzing carboxylesterase from mouse liver microsomes.	2004 Jul 9	15123619
Effectiveness of residual spraying of peridomestic ecotopes with deltamethrin and permethrin on Triatoma infestans in rural western Argentina: a district-wide randomized trial.	2004 Mar	15112008
Separation and aquatic toxicity of enantiomers of synthetic pyrethroid insecticides.	2005	15806620
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
Rapid analysis of pyrethroids in whole urine by high-performance liquid chromatography using a monolithic column and off-line preconcentration in a restricted access material cartridge.	2005 May	15719232
Lessons learned for the assessment of children's pesticide exposure: critical sampling and analytical issues for future studies.	2005 Oct	16203262
Purification and characterization of a novel pyrethroid hydrolase from Aspergillus niger ZD11.	2005 Sep 21	16159167
Laboratory and scaled up evaluation of cis-permethrin applied as a new ultra low volume formulation against Aedes aegypti (Diptera: Culicidae).	2006 Jan	16174514
An intervention to reduce residential insecticide exposure during pregnancy among an inner-city cohort.	2006 Nov	17107853
Method of analysis of a selected group of pyrethroids in soil samples using off-line flow-through extraction and on-column direct large-volume injection in reversed phase high performance liquid chromatography.	2006 Sep	17069244
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
Multimedia measurements and activity patterns in an observational pilot study of nine young children.	2008 Jan	17851450
Pesticides and atopic and nonatopic asthma among farm women in the Agricultural Health Study.	2008 Jan 1	17932376
Induction of hepatic estrogen-responsive gene transcription by permethrin enantiomers in male adult zebrafish.	2008 Jun 23	18499281
High-resolution melt analysis for the detection of a mutation associated with permethrin resistance in a population of scabies mites.	2008 Mar	18380658
Neurobehavioral toxicology of pyrethroid insecticides in adult animals: a critical review.	2008 Mar-Apr	18206347
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
The effect of insecticide synergists on the response of scabies mites to pyrethroid acaricides.	2009	19125173
Ability of four emergent macrophytes to remediate permethrin in mesocosm experiments.	2009 Aug	19458989
Pyrethroid insecticides: isoform-dependent hydrolysis, induction of cytochrome P450 3A4 and evidence on the involvement of the pregnane X receptor.	2009 May 15	19249324
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
Time-dependent integrity during storage of natural surface water samples for the trace analysis of pharmaceutical products, feminizing hormones and pesticides.	2010 Apr 19	20403158
Assessing hormone receptor activities of pyrethroid insecticides and their metabolites in reporter gene assays.	2010 Jul	20410157
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
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
Permethrin treatment of head lice with knockdown resistance-like gene.	2011 Jan 27	21268748
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.	2011 Sep 14	21786822
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
Early life permethrin exposure induces long-term brain changes in Nurr1, NF-kB and Nrf-2.	2013 Jun 17	23566817
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 `Sat Dec 16 19:22:38 GMT 2023` Edited by `admin` on `Sat Dec 16 19:22:38 GMT 2023`
Record UNII	509F88P9SZ
Record Status	`Validated (UNII)`
Record Version

Download

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