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=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 1430
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 1430
Voltage-sensitive sodium channel 7 Target ID: CHEMBL2362985 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25390654	Inhibitor 8297

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 8429	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 8429	NIX Approved Use To treat head lice. Launch Date 1990
Pediculosis 9 Sources: https://www.drugs.com/monograph/permethrin.html	Curative	Approved 8429	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 8429	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
49.46 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768	460 mg/kg single, oral dose: 460 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	PERMETHRIN plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029	10 mg/kg bw single, oral dose: 10 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	PERMETHRIN serum	Gallus gallus domesticus population: HEALTHY 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
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

AUC

Value	Dose	Analyte	Population
159 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768	46 mg/kg single, intravenous dose: 46 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PERMETHRIN plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED
965 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768	460 mg/kg single, oral dose: 460 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	PERMETHRIN plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.95 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029	10 mg/kg bw single, oral dose: 10 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	PERMETHRIN serum	Gallus gallus domesticus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
16.45 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029	10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	PERMETHRIN serum	Gallus gallus domesticus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
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	Analyte	Population
8.67 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768	46 mg/kg single, intravenous dose: 46 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PERMETHRIN plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED
12.37 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1871768	460 mg/kg single, oral dose: 460 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	PERMETHRIN plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.54 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029	10 mg/kg bw single, oral dose: 10 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:	PERMETHRIN serum	Gallus gallus domesticus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
4.73 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26302029	10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:	PERMETHRIN serum	Gallus gallus domesticus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
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 Condition: pediculosis 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 Condition: scabies 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 Condition: crusted scabies 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 Condition: pediculosis 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 Condition: scabies Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/31985943/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2B6 810 P-gp 1461	CYP2B6 664 CYP1A2 1054 CYP2C8 693 CYP2C19 991 CYP3A5 395 CYP2A6 543 CYP2E1 667 CYP3A7 110 CYP4A11 119 CES1 22 CES2 28 P-gp 1537

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/24014652/	no
CYP2B6 1001	inhibitor 3277 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=052645531	yes

Drug as victim

Target	Modality	Activity
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP3A5 395	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	likely
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
CYP3A7 110	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
CYP4A11 119	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	no
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/24014652/	yes [Km 2.8 uM]
CES1 22	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	yes
CES2 28	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	yes
CYP2B6 664	substrate 3367 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=052645531	yes
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29779438/	yes
CYP3A4 1737	substrate 3367 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
MolPort	MolPort-003-933-021	https://www.molport.com/shop/molecule-link/MolPort-003-933-021
eMolecules	508544	https://www.emolecules.com/cgi-bin/more?vid=508544

PubMed

Title	Date	PubMed
Radiosynthesis and metabolism in rats of the 1R isomers of the insecticide permethrin.	1976 Mar-Apr	1254806
Purification and preliminary characterization of permethrinase from a pyrethroid-transforming strain of Bacillus cereus.	1993 Jul	8357241
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
Determination of solid-liquid partition coefficients (K(d)) for diazinon, propetamphos and cis-permethrin: implications for sheep dip disposal.	2004 Aug 15	15262167
Identification, expression, and purification of a pyrethroid-hydrolyzing carboxylesterase from mouse liver microsomes.	2004 Jul 9	15123619
Effectiveness of residual spraying of peridomestic ecotopes with deltamethrin and permethrin on Triatoma infestans in rural western Argentina: a district-wide randomized trial.	2004 Mar	15112008
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
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
An intervention to reduce residential insecticide exposure during pregnancy among an inner-city cohort.	2006 Nov	17107853
Enantiomeric differences in permethrin degradation pathways in soil and sediment.	2006 Nov 29	17117803
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 Sep	17069244
Permethrin may disrupt testosterone biosynthesis via mitochondrial membrane damage of Leydig cells in adult male mouse.	2007 Aug	17463061
Pesticides and their metabolites in the homes and urine of farmworker children living in the Salinas Valley, CA.	2007 Jul	16736054
An observational study of 127 preschool children at their homes and daycare centers in Ohio: environmental pathways to cis- and trans-permethrin exposure.	2007 Jun	17258193
The in vitro metabolism of a pyrethroid insecticide, permethrin, and its hydrolysis products in rats.	2007 Jun 25	17451859
Synergism between cis-permethrin and benzoyl phenyl urea insect growth regulators against Aedes aegypti larvae.	2007 Mar	17536364
Hydrolysis of pyrethroids by human and rat tissues: examination of intestinal, liver and serum carboxylesterases.	2007 May 15	17442360
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
Permethrin may induce adult male mouse reproductive toxicity due to cis isomer not trans isomer.	2008 Jun 27	18455858
Mitigation assessment of vegetated drainage ditches for collecting irrigation runoff in California.	2008 Mar-Apr	18268312
Neurobehavioral toxicology of pyrethroid insecticides in adult animals: a critical review.	2008 Mar-Apr	18206347
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
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
American Healthy Homes Survey: a national study of residential pesticides measured from floor wipes.	2009 Jun 15	19603637
Evidence for dose-additive effects of pyrethroids on motor activity in rats.	2009 Oct	20019907
Parallel metatranscriptome analyses of host and symbiont gene expression in the gut of the termite Reticulitermes flavipes.	2009 Oct 15	19832970
Effects of several pyrethroids on hepatic cytochrome P450 activities in rats.	2010 Apr	20009351
Time-dependent integrity during storage of natural surface water samples for the trace analysis of pharmaceutical products, feminizing hormones and pesticides.	2010 Apr 19	20403158
In vitro dermal absorption of pyrethroid pesticides in human and rat skin.	2010 Jul	20398685
Distribution and determinants of pesticide mixtures in cord serum using principal component analysis.	2010 Jul 15	20550184
Isotope dilution gas chromatography/mass spectrometry method for determination of pyrethroids in apple juice.	2010 Mar	20101497
Current and historically used pesticides in residential soil from 11 homes in Atlanta, Georgia, USA.	2010 May	20016886
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.	2011 Sep 14	21786822

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 `Sat Dec 16 08:42:53 GMT 2023` Edited by `admin` on `Sat Dec 16 08:42:53 GMT 2023`
Record UNII	GC30YV53C8
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PERMETHRIN, CIS-

Common Name

English

1RS,CIS-PERMETHRIN

Common Name

English

CISPERMETHRIN

Common Name

English

(±)-CIS-PERMETHRIN

Common Name

English

(±)-CIS-FMC-33297

Code

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