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
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.	2011-09-14	21786822
Distribution and determinants of pesticide mixtures in cord serum using principal component analysis.	2010-07-15	20550184
In vitro dermal absorption of pyrethroid pesticides in human and rat skin.	2010-07	20398685
Current and historically used pesticides in residential soil from 11 homes in Atlanta, Georgia, USA.	2010-05	20016886
Time-dependent integrity during storage of natural surface water samples for the trace analysis of pharmaceutical products, feminizing hormones and pesticides.	2010-04-19	20403158
Effects of several pyrethroids on hepatic cytochrome P450 activities in rats.	2010-04	20009351
Isotope dilution gas chromatography/mass spectrometry method for determination of pyrethroids in apple juice.	2010-03	20101497
Parallel metatranscriptome analyses of host and symbiont gene expression in the gut of the termite Reticulitermes flavipes.	2009-10-15	19832970
Evidence for dose-additive effects of pyrethroids on motor activity in rats.	2009-10	20019907
Ability of four emergent macrophytes to remediate permethrin in mesocosm experiments.	2009-08	19458989
American Healthy Homes Survey: a national study of residential pesticides measured from floor wipes.	2009-06-15	19603637
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.	2009-04-10	19233371
In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms.	2009-01	18948380
Measuring pyrethroids in sediment pore water using matrix-solid phase microextraction.	2009-01	18712946
Molecular cloning and characterization of a novel pyrethroid-hydrolyzing esterase originating from the Metagenome.	2008-12-30	19116015
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.	2008-12	19079720
Permethrin may induce adult male mouse reproductive toxicity due to cis isomer not trans isomer.	2008-06-27	18455858
Mitigation assessment of vegetated drainage ditches for collecting irrigation runoff in California.	2008-02-13	18268312
Multimedia measurements and activity patterns in an observational pilot study of nine young children.	2008-01	17851450
Efficacy of permethrin cream and oral ivermectin in treatment of scabies.	2007-10	17978449
Permethrin may disrupt testosterone biosynthesis via mitochondrial membrane damage of Leydig cells in adult male mouse.	2007-08	17463061
Neurobehavioral toxicology of pyrethroid insecticides in adult animals: a critical review.	2007-07-13	18206347
Pesticides and their metabolites in the homes and urine of farmworker children living in the Salinas Valley, CA.	2007-07	16736054
The in vitro metabolism of a pyrethroid insecticide, permethrin, and its hydrolysis products in rats.	2007-06-25	17451859
An observational study of 127 preschool children at their homes and daycare centers in Ohio: environmental pathways to cis- and trans-permethrin exposure.	2007-06	17258193
Hydrolysis of pyrethroids by human and rat tissues: examination of intestinal, liver and serum carboxylesterases.	2007-05-15	17442360
Synergism between cis-permethrin and benzoyl phenyl urea insect growth regulators against Aedes aegypti larvae.	2007-03	17536364
Enantiomeric differences in permethrin degradation pathways in soil and sediment.	2006-11-29	17117803
An intervention to reduce residential insecticide exposure during pregnancy among an inner-city cohort.	2006-11	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.	2006-09	17069244
Enantioselective degradation and chiral stability of pyrethroids in soil and sediment.	2006-07-12	16819914
Hydrolytic metabolism of pyrethroids by human and other mammalian carboxylesterases.	2006-02-28	16387282
Molecular cloning, purification, and biochemical characterization of a novel pyrethroid-hydrolyzing esterase from Klebsiella sp. strain ZD112.	2006-02-08	16448191
Laboratory and scaled up evaluation of cis-permethrin applied as a new ultra low volume formulation against Aedes aegypti (Diptera: Culicidae).	2006-01	16174514
Lessons learned for the assessment of children's pesticide exposure: critical sampling and analytical issues for future studies.	2005-10	16203262
Purification and characterization of a novel pyrethroid hydrolase from Aspergillus niger ZD11.	2005-09-21	16159167
HER-2/neu and CD117 (c-kit) overexpression in patients with pesticide exposure and extensive stage small cell lung carcinoma (ESSCLC).	2005-06-09	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.	2005-05	15719232
Identification of amino acid residues in the insect sodium channel critical for pyrethroid binding.	2005-02	15525757
Enantioselectivity in environmental safety of current chiral insecticides.	2005-01-18	15632216
Diffusion of the synthetic pyrethroid permethrin into bed-sediments.	2005-01-15	15707052
Separation and aquatic toxicity of enantiomers of synthetic pyrethroid insecticides.	2005	15806620
Determination of solid-liquid partition coefficients (K(d)) for diazinon, propetamphos and cis-permethrin: implications for sheep dip disposal.	2004-08-15	15262167
Identification, expression, and purification of a pyrethroid-hydrolyzing carboxylesterase from mouse liver microsomes.	2004-07-09	15123619
[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals].	2004-04	15272608
Effectiveness of residual spraying of peridomestic ecotopes with deltamethrin and permethrin on Triatoma infestans in rural western Argentina: a district-wide randomized trial.	2004-03	15112008
Determination of pyrethrin and pyrethroid pesticides in urine and water matrixes by liquid chromatography with diode array detection.	2004-02-26	14979708
Inhibition of trans-permethrin hydrolysis in human liver fractions by chloropyrifos oxon and carbaryl.	2004	15663293
Purification and preliminary characterization of permethrinase from a pyrethroid-transforming strain of Bacillus cereus.	1993-07	8357241
Radiosynthesis and metabolism in rats of the 1R isomers of the insecticide permethrin.	1976-03-01	1254806

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