PERMETHRIN, CIS-(+)-

Details

Stereochemistry	ABSOLUTE
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=CC(OC3=CC=CC=C3)=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
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
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
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
Microbial transformation of pyrethroid insecticides in aqueous and sediment phases.	2004 Jan	14768859
Separation and aquatic toxicity of enantiomers of synthetic pyrethroid insecticides.	2005	15806620
Potential estrogenic and antiandrogenic effects of permethrin in rats.	2005 Apr	15599112
Elevated activity of an Epsilon class glutathione transferase confers DDT resistance in the dengue vector, Aedes aegypti.	2005 Aug	15944082
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
Hydrolysis of pyrethroids by carboxylesterases from Lucilia cuprina and Drosophila melanogaster with active sites modified by in vitro mutagenesis.	2005 Jun	15857765
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
Laboratory and scaled up evaluation of cis-permethrin applied as a new ultra low volume formulation against Aedes aegypti (Diptera: Culicidae).	2006 Jan	16174514
Enantioselective degradation and chiral stability of pyrethroids in soil and sediment.	2006 Jul 12	16819914
Pyrethroid pesticide-induced alterations in dopamine transporter function.	2006 Mar 15	16005927
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Pesticide use and chronic bronchitis among farmers in the Agricultural Health Study.	2007 Dec	17975796
Molecular cloning and characterization of a novel pyrethroid-hydrolyzing esterase originating from the Metagenome.	2008 Dec 30	19116015
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
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
Transcriptional response of rat frontal cortex following acute in vivo exposure to the pyrethroid insecticides permethrin and deltamethrin.	2008 Nov 18	19017407
Design of a compressed air modulator to be used in comprehensive multidimensional gas chromatography and its application in the determination of pesticide residues in grapes.	2009 Apr 10	19233371
Ability of four emergent macrophytes to remediate permethrin in mesocosm experiments.	2009 Aug	19458989
American Healthy Homes Survey: a national study of residential pesticides measured from floor wipes.	2009 Jun 15	19603637
Enantioselective induction of estrogen-responsive gene expression by permethrin enantiomers in embryo-larval zebrafish.	2009 Mar	19095286
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
Parallel metatranscriptome analyses of host and symbiont gene expression in the gut of the termite Reticulitermes flavipes.	2009 Oct 15	19832970
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
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
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

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 22:57:08 GMT 2025` Edited by `admin` on `Mon Mar 31 22:57:08 GMT 2025`
Record UNII	620Q217008
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PERMETHRIN, CIS-(+)-

Common Name

English

NRDC-167

Preferred Name

English

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

Systematic Name

English

1R-CIS-PERMETHRIN

Common Name

English

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

Systematic Name

English

(+)-CIS-PERMETHRIN

Common Name

English

Code System Code Type Description

CAS

54774-45-7

Created by admin on Mon Mar 31 22:57:08 GMT 2025 , Edited by admin on Mon Mar 31 22:57:08 GMT 2025

PRIMARY

EPA CompTox

DTXSID5052208

Created by admin on Mon Mar 31 22:57:08 GMT 2025 , Edited by admin on Mon Mar 31 22:57:08 GMT 2025

PRIMARY

FDA UNII

620Q217008

Created by admin on Mon Mar 31 22:57:08 GMT 2025 , Edited by admin on Mon Mar 31 22:57:08 GMT 2025

PRIMARY

PUBCHEM

40463

Created by admin on Mon Mar 31 22:57:08 GMT 2025 , Edited by admin on Mon Mar 31 22:57:08 GMT 2025

PRIMARY

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PERMETHRIN, CIS-(-)-

ENANTIOMER -> ENANTIOMER

Amount:

Details

SMILES

InChI

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

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

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

C_max

T_1/2

F_unbound

Drug as perpetrator