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
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
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2362985 |
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Target ID: CHEMBL2362984 |
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Target ID: CHEMBL2362985 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25390654 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | ELIMITE Approved UseELIMITE (permethrin) 5% Cream is indicated for the treatment of infestation with Sarcoptesscabiei (scabies). Launch Date1989 |
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Curative | NIX Approved UseTo treat head lice. Launch Date1990 |
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Curative | NIX Approved UseA 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 Date1986 |
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Curative | NIX Approved UseA 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 Date1986 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
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: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: |
Other AEs: Skin and subcutaneous conditions NEC... |
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
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: |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
likely | ||||
likely | ||||
likely | ||||
likely | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes [Km 2.8 uM] | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Radiosynthesis and metabolism in rats of the 1R isomers of the insecticide permethrin. | 1976 Mar-Apr |
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Insecticide induced disruptions in functioning of developing brain of Rana cyanophlictis. | 1992 Aug |
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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 |
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Molecular mechanisms of cis-urocanic acid and permethrin-induced alterations in cutaneous immunity. | 2003 Dec |
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Transfer efficiencies of pesticides from household flooring surfaces to foods. | 2003 Nov |
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Differential up-regulation of striatal dopamine transporter and alpha-synuclein by the pyrethroid insecticide permethrin. | 2003 Nov 1 |
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Determination of pyrethrin and pyrethroid pesticides in urine and water matrixes by liquid chromatography with diode array detection. | 2003 Nov-Dec |
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Inhibition of trans-permethrin hydrolysis in human liver fractions by chloropyrifos oxon and carbaryl. | 2004 |
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[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals]. | 2004 Apr |
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Co-exposure to pyridostigmine bromide, DEET, and/or permethrin causes sensorimotor deficit and alterations in brain acetylcholinesterase activity. | 2004 Feb |
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Neurological deficits induced by malathion, DEET, and permethrin, alone or in combination in adult rats. | 2004 Feb 27 |
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Microbial transformation of pyrethroid insecticides in aqueous and sediment phases. | 2004 Jan |
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The immunosuppressive effect of alpha-permethrin on Indian major carp, rohu (Labeo rohita Ham.). | 2004 Jan |
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Separation and aquatic toxicity of enantiomers of synthetic pyrethroid insecticides. | 2005 |
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Identification of amino acid residues in the insect sodium channel critical for pyrethroid binding. | 2005 Feb |
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Diffusion of the synthetic pyrethroid permethrin into bed-sediments. | 2005 Jan 15 |
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Enantioselectivity in environmental safety of current chiral insecticides. | 2005 Jan 18 |
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HER-2/neu and CD117 (c-kit) overexpression in patients with pesticide exposure and extensive stage small cell lung carcinoma (ESSCLC). | 2005 Jun 9 |
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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 |
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Lessons learned for the assessment of children's pesticide exposure: critical sampling and analytical issues for future studies. | 2005 Oct |
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Purification and characterization of a novel pyrethroid hydrolase from Aspergillus niger ZD11. | 2005 Sep 21 |
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Hydrolytic metabolism of pyrethroids by human and other mammalian carboxylesterases. | 2006 Feb 28 |
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Molecular cloning, purification, and biochemical characterization of a novel pyrethroid-hydrolyzing esterase from Klebsiella sp. strain ZD112. | 2006 Feb 8 |
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Pesticides and their metabolites in the homes and urine of farmworker children living in the Salinas Valley, CA. | 2007 Jul |
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Efficacy of permethrin cream and oral ivermectin in treatment of scabies. | 2007 Oct |
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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 |
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Molecular cloning and characterization of a novel pyrethroid-hydrolyzing esterase originating from the Metagenome. | 2008 Dec 30 |
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Multimedia measurements and activity patterns in an observational pilot study of nine young children. | 2008 Jan |
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Induction of hepatic estrogen-responsive gene transcription by permethrin enantiomers in male adult zebrafish. | 2008 Jun 23 |
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Permethrin may induce adult male mouse reproductive toxicity due to cis isomer not trans isomer. | 2008 Jun 27 |
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Neurobehavioral toxicology of pyrethroid insecticides in adult animals: a critical review. | 2008 Mar-Apr |
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Cross-induction of detoxification genes by environmental xenobiotics and insecticides in the mosquito Aedes aegypti: impact on larval tolerance to chemical insecticides. | 2008 May |
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Transcriptional response of rat frontal cortex following acute in vivo exposure to the pyrethroid insecticides permethrin and deltamethrin. | 2008 Nov 18 |
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The effect of insecticide synergists on the response of scabies mites to pyrethroid acaricides. | 2009 |
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Ability of four emergent macrophytes to remediate permethrin in mesocosm experiments. | 2009 Aug |
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In vitro metabolism of pyrethroid pesticides by rat and human hepatic microsomes and cytochrome p450 isoforms. | 2009 Jan |
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Measuring pyrethroids in sediment pore water using matrix-solid phase microextraction. | 2009 Jan |
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Human carboxylesterases HCE1 and HCE2: ontogenic expression, inter-individual variability and differential hydrolysis of oseltamivir, aspirin, deltamethrin and permethrin. | 2009 Jan 15 |
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Enantioselective induction of estrogen-responsive gene expression by permethrin enantiomers in embryo-larval zebrafish. | 2009 Mar |
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Parallel metatranscriptome analyses of host and symbiont gene expression in the gut of the termite Reticulitermes flavipes. | 2009 Oct 15 |
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Estrogenic pyrethroid pesticides regulate expression of estrogen receptor transcripts in mouse Sertoli cells differently from 17beta-estradiol. | 2010 |
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Estrogenic activities of two synthetic pyrethroids and their metabolites. | 2010 |
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Assessing hormone receptor activities of pyrethroid insecticides and their metabolites in reporter gene assays. | 2010 Jul |
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Circadian clock regulates response to pesticides in Drosophila via conserved Pdp1 pathway. | 2010 Jun |
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Splice variant specific increase in Ca2+/calmodulin-dependent protein kinase 1-gamma mRNA expression in response to acute pyrethroid exposure. | 2010 May-Jun |
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Pesticide use modifies the association between genetic variants on chromosome 8q24 and prostate cancer. | 2010 Nov 15 |
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Fetal exposure to chlordane and permethrin mixtures in relation to inflammatory cytokines and birth outcomes. | 2011 Feb 15 |
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High frequency of mutations associated with head lice pyrethroid resistance in schoolchildren from Bobigny, France. | 2011 Jan |
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Early life permethrin insecticide treatment leads to heart damage in adult rats. | 2011 Sep |
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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
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:16:03 GMT 2025
by
admin
on
Mon Mar 31 22:16:03 GMT 2025
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Record UNII |
GC30YV53C8
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Record Status |
Validated (UNII)
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Record Version |
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-
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EPA PESTICIDE CODE |
209500
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GC30YV53C8
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61949-76-6
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DTXSID0038338
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52341-33-0
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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
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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