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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 of PERMETHRIN, CIS-

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

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

Curator's Comment: Permethrin was allegedly developed by US military to protect soldiers from insects in the jungle. (https://www.oammagazine.com/wp-content/uploads/2016/04/Treating%20your%20Clothes%20with%20Permethrin.pdf).

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ELIMITE

Approved Use

ELIMITE (permethrin) 5% Cream is indicated for the treatment of infestation with Sarcoptesscabiei (scabies).

Launch Date

1989
Curative
NIX

Approved Use

To treat head lice.

Launch Date

1990
Curative
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
Curative
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
868 ng/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
2.73 μg × h/mL
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.08 h
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
PERMETHRIN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 % 1 times / day multiple, topical
Recommended
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Other AEs: Skin and subcutaneous conditions NEC...
Other AEs:
Skin and subcutaneous conditions NEC
Sources:
5 % 1 times / day multiple, topical
Recommended
Dose: 5 %, 1 times / day
Route: topical
Route: multiple
Dose: 5 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Other AEs: Dystonia...
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Dystonia
5 % 1 times / day multiple, topical
Recommended
Dose: 5 %, 1 times / day
Route: topical
Route: multiple
Dose: 5 %, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Radiosynthesis and metabolism in rats of the 1R isomers of the insecticide permethrin.
1976 Mar-Apr
Insecticide induced disruptions in functioning of developing brain of Rana cyanophlictis.
1992 Aug
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
Molecular mechanisms of cis-urocanic acid and permethrin-induced alterations in cutaneous immunity.
2003 Dec
Transfer efficiencies of pesticides from household flooring surfaces to foods.
2003 Nov
Differential up-regulation of striatal dopamine transporter and alpha-synuclein by the pyrethroid insecticide permethrin.
2003 Nov 1
Determination of pyrethrin and pyrethroid pesticides in urine and water matrixes by liquid chromatography with diode array detection.
2003 Nov-Dec
Inhibition of trans-permethrin hydrolysis in human liver fractions by chloropyrifos oxon and carbaryl.
2004
[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals].
2004 Apr
Co-exposure to pyridostigmine bromide, DEET, and/or permethrin causes sensorimotor deficit and alterations in brain acetylcholinesterase activity.
2004 Feb
Neurological deficits induced by malathion, DEET, and permethrin, alone or in combination in adult rats.
2004 Feb 27
Microbial transformation of pyrethroid insecticides in aqueous and sediment phases.
2004 Jan
The immunosuppressive effect of alpha-permethrin on Indian major carp, rohu (Labeo rohita Ham.).
2004 Jan
Separation and aquatic toxicity of enantiomers of synthetic pyrethroid insecticides.
2005
Identification of amino acid residues in the insect sodium channel critical for pyrethroid binding.
2005 Feb
Diffusion of the synthetic pyrethroid permethrin into bed-sediments.
2005 Jan 15
Enantioselectivity in environmental safety of current chiral insecticides.
2005 Jan 18
HER-2/neu and CD117 (c-kit) overexpression in patients with pesticide exposure and extensive stage small cell lung carcinoma (ESSCLC).
2005 Jun 9
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
Lessons learned for the assessment of children's pesticide exposure: critical sampling and analytical issues for future studies.
2005 Oct
Purification and characterization of a novel pyrethroid hydrolase from Aspergillus niger ZD11.
2005 Sep 21
Hydrolytic metabolism of pyrethroids by human and other mammalian carboxylesterases.
2006 Feb 28
Molecular cloning, purification, and biochemical characterization of a novel pyrethroid-hydrolyzing esterase from Klebsiella sp. strain ZD112.
2006 Feb 8
Pesticides and their metabolites in the homes and urine of farmworker children living in the Salinas Valley, CA.
2007 Jul
Efficacy of permethrin cream and oral ivermectin in treatment of scabies.
2007 Oct
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
Molecular cloning and characterization of a novel pyrethroid-hydrolyzing esterase originating from the Metagenome.
2008 Dec 30
Multimedia measurements and activity patterns in an observational pilot study of nine young children.
2008 Jan
Induction of hepatic estrogen-responsive gene transcription by permethrin enantiomers in male adult zebrafish.
2008 Jun 23
Permethrin may induce adult male mouse reproductive toxicity due to cis isomer not trans isomer.
2008 Jun 27
Neurobehavioral toxicology of pyrethroid insecticides in adult animals: a critical review.
2008 Mar-Apr
Cross-induction of detoxification genes by environmental xenobiotics and insecticides in the mosquito Aedes aegypti: impact on larval tolerance to chemical insecticides.
2008 May
Transcriptional response of rat frontal cortex following acute in vivo exposure to the pyrethroid insecticides permethrin and deltamethrin.
2008 Nov 18
The effect of insecticide synergists on the response of scabies mites to pyrethroid acaricides.
2009
Ability of four emergent macrophytes to remediate permethrin in mesocosm experiments.
2009 Aug
In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms.
2009 Jan
Measuring pyrethroids in sediment pore water using matrix-solid phase microextraction.
2009 Jan
Human carboxylesterases HCE1 and HCE2: ontogenic expression, inter-individual variability and differential hydrolysis of oseltamivir, aspirin, deltamethrin and permethrin.
2009 Jan 15
Enantioselective induction of estrogen-responsive gene expression by permethrin enantiomers in embryo-larval zebrafish.
2009 Mar
Parallel metatranscriptome analyses of host and symbiont gene expression in the gut of the termite Reticulitermes flavipes.
2009 Oct 15
Estrogenic pyrethroid pesticides regulate expression of estrogen receptor transcripts in mouse Sertoli cells differently from 17beta-estradiol.
2010
Estrogenic activities of two synthetic pyrethroids and their metabolites.
2010
Assessing hormone receptor activities of pyrethroid insecticides and their metabolites in reporter gene assays.
2010 Jul
Circadian clock regulates response to pesticides in Drosophila via conserved Pdp1 pathway.
2010 Jun
Splice variant specific increase in Ca2+/calmodulin-dependent protein kinase 1-gamma mRNA expression in response to acute pyrethroid exposure.
2010 May-Jun
Pesticide use modifies the association between genetic variants on chromosome 8q24 and prostate cancer.
2010 Nov 15
Fetal exposure to chlordane and permethrin mixtures in relation to inflammatory cytokines and birth outcomes.
2011 Feb 15
High frequency of mutations associated with head lice pyrethroid resistance in schoolchildren from Bobigny, France.
2011 Jan
Early life permethrin insecticide treatment leads to heart damage in adult rats.
2011 Sep
Do pollutants affect insecticide-driven gene selection in mosquitoes? Experimental evidence from transcriptomics.
2012 Jun 15
Patents

Sample Use Guides

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
  • Download
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
Created by admin on Mon Mar 31 22:16:03 GMT 2025 , Edited by admin on Mon Mar 31 22:16:03 GMT 2025
Code System Code Type Description
FDA UNII
GC30YV53C8
Created by admin on Mon Mar 31 22:16:03 GMT 2025 , Edited by admin on Mon Mar 31 22:16:03 GMT 2025
PRIMARY
CAS
61949-76-6
Created by admin on Mon Mar 31 22:16:03 GMT 2025 , Edited by admin on Mon Mar 31 22:16:03 GMT 2025
PRIMARY
EPA CompTox
DTXSID0038338
Created by admin on Mon Mar 31 22:16:03 GMT 2025 , Edited by admin on Mon Mar 31 22:16:03 GMT 2025
PRIMARY
CAS
52341-33-0
Created by admin on Mon Mar 31 22:16:03 GMT 2025 , Edited by admin on Mon Mar 31 22:16:03 GMT 2025
SUPERSEDED
ECHA (EC/EINECS)
263-346-3
Created by admin on Mon Mar 31 22:16:03 GMT 2025 , Edited by admin on Mon Mar 31 22:16:03 GMT 2025
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE