PERMETHRIN, CIS-

Details

Stereochemistry	RACEMIC
Molecular Formula	C21H20Cl2O3
Molecular Weight	391.288
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)OCC2=CC(OC3=CC=CC=C3)=CC=C2

InChI

InChIKey=RLLPVAHGXHCWKJ-HKUYNNGSSA-N

InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3/t17-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H20Cl2O3
Molecular Weight	391.288
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Insecticide induced disruptions in functioning of developing brain of Rana cyanophlictis.	1992 Aug	1459649
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
Molecular mechanisms of cis-urocanic acid and permethrin-induced alterations in cutaneous immunity.	2003 Dec	14617103
Transfer efficiencies of pesticides from household flooring surfaces to foods.	2003 Nov	14603346
Differential up-regulation of striatal dopamine transporter and alpha-synuclein by the pyrethroid insecticide permethrin.	2003 Nov 1	14575646
Determination of pyrethrin and pyrethroid pesticides in urine and water matrixes by liquid chromatography with diode array detection.	2003 Nov-Dec	14979708
Inhibition of trans-permethrin hydrolysis in human liver fractions by chloropyrifos oxon and carbaryl.	2004	15663293
[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals].	2004 Apr	15272608
Co-exposure to pyridostigmine bromide, DEET, and/or permethrin causes sensorimotor deficit and alterations in brain acetylcholinesterase activity.	2004 Feb	14751452
Neurological deficits induced by malathion, DEET, and permethrin, alone or in combination in adult rats.	2004 Feb 27	14713564
Microbial transformation of pyrethroid insecticides in aqueous and sediment phases.	2004 Jan	14768859
The immunosuppressive effect of alpha-permethrin on Indian major carp, rohu (Labeo rohita Ham.).	2004 Jan	14675832
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
Diffusion of the synthetic pyrethroid permethrin into bed-sediments.	2005 Jan 15	15707052
Enantioselectivity in environmental safety of current chiral insecticides.	2005 Jan 18	15632216
HER-2/neu and CD117 (c-kit) overexpression in patients with pesticide exposure and extensive stage small cell lung carcinoma (ESSCLC).	2005 Jun 9	15946380
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
Hydrolytic metabolism of pyrethroids by human and other mammalian carboxylesterases.	2006 Feb 28	16387282
Molecular cloning, purification, and biochemical characterization of a novel pyrethroid-hydrolyzing esterase from Klebsiella sp. strain ZD112.	2006 Feb 8	16448191
Pesticides and their metabolites in the homes and urine of farmworker children living in the Salinas Valley, CA.	2007 Jul	16736054
Efficacy of permethrin cream and oral ivermectin in treatment of scabies.	2007 Oct	17978449
Changes in pest infestation levels, self-reported pesticide use, and permethrin exposure during pregnancy after the 2000-2001 U.S. Environmental Protection Agency restriction of organophosphates.	2008 Dec	19079720
Molecular cloning and characterization of a novel pyrethroid-hydrolyzing esterase originating from the Metagenome.	2008 Dec 30	19116015
Multimedia measurements and activity patterns in an observational pilot study of nine young children.	2008 Jan	17851450
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
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
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
Ability of four emergent macrophytes to remediate permethrin in mesocosm experiments.	2009 Aug	19458989
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
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
Parallel metatranscriptome analyses of host and symbiont gene expression in the gut of the termite Reticulitermes flavipes.	2009 Oct 15	19832970
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
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
Pesticide use modifies the association between genetic variants on chromosome 8q24 and prostate cancer.	2010 Nov 15	20978189
Fetal exposure to chlordane and permethrin mixtures in relation to inflammatory cytokines and birth outcomes.	2011 Feb 15	21235202
High frequency of mutations associated with head lice pyrethroid resistance in schoolchildren from Bobigny, France.	2011 Jan	21337951
Early life permethrin insecticide treatment leads to heart damage in adult rats.	2011 Sep	21616133
Do pollutants affect insecticide-driven gene selection in mosquitoes? Experimental evidence from transcriptomics.	2012 Jun 15	22406618

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	Chemical Created by `admin` on `Mon Mar 31 22:16:03 GMT 2025` Edited by `admin` on `Mon Mar 31 22:16:03 GMT 2025`
Record UNII	GC30YV53C8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PERMETHRIN, CIS-

Common Name

English

(±)-CIS-FMC-33297

Preferred Name

English

1RS,CIS-PERMETHRIN

Common Name

English

CISPERMETHRIN

Common Name

English

(±)-CIS-PERMETHRIN

Common Name

English

PERMETHRIN, CIS-(±)-

Common Name

English

CYCLOPROPANECARBOXYLIC ACID, 3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYL-, (3-PHENOXYPHENYL)METHYL ESTER, (1R,3R)-REL-

Systematic Name

English

NRDC-148

Code

English

FMC-35171

Code

English

CIS-PERMETHRIN

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

209500