CYPERMETHRIN

Details

Stereochemistry	MIXED
Molecular Formula	C22H19Cl2NO3
Molecular Weight	416.297
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C2=CC=CC(OC3=CC=CC=C3)=C2

InChI

InChIKey=KAATUXNTWXVJKI-UHFFFAOYSA-N

InChI=1S/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3

HIDE SMILES / InChI

Molecular Formula	C22H19Cl2NO3
Molecular Weight	416.297
Charge	0
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://cdpr.ca.gov/docs/emon/pubs/fatememo/cyperm.pdf | http://parasitipedia.net/index.php?option=com_content&view=article&id=2455&Itemid=2723 | http://www.inchem.org/documents/pims/chemical/pim163.htm

Cypermethrin is a synthetic, pyrethroid insecticide that has high insecticidal activity, low avian and mammalian toxicity. Cypermethrin works by quickly affecting the insect’s central nervous system. The major target site of cypermethrin is the sodium channel of the nerve membrane. A sodium channel exposed to cypermethrin can remain open much longer, even up to several seconds. It is used to control many pests including lepidopterous pests of cotton, fruit, and vegetable crops. In veterinary, it is applied topically for the control of ectoparasites such as ticks, fleas, lice and blowflies.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-dependent sodium channels (ticks and insects) 1 Target ID: Voltage-dependent sodium channels (ticks and insects) Sources: http://www.inchem.org/documents/pims/chemical/pim163.htm \| http://cdpr.ca.gov/docs/emon/pubs/fatememo/cyperm.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/9658558	Opener 34

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pediculosis 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10330558 https://www.ncbi.nlm.nih.gov/pubmed/8929186	Curative		Approved 8583	ECTOMETHRIN Approved Use Indicated for the control and treatment of infestations of horn flies, sucking and biting lice, and as repellent of horse flies, flies and mosquitos.
Ectoparasitic infestations 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23826989 https://www.ncbi.nlm.nih.gov/pubmed/19398160 https://www.ncbi.nlm.nih.gov/pubmed/22526295 https://www.ncbi.nlm.nih.gov/pubmed/23733232	Curative		Approved 8583	ECTOMETHRIN Approved Use Indicated for the control and treatment of infestations of horn flies, sucking and biting lice, and as repellent of horse flies, flies and mosquitos.

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 2057 CYP1A2 2153 CYP2E1 1060 CYP19A1 429	P-gp 2052	CYP1A2 832 CYP2B6 669 CYP2A6 86

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2912#section=Biological-Test-Results Page: 10.0	inconclusive [IC50 31.7055 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2912#section=Biological-Test-Results Page: 14.0	inconclusive [IC50 56.3813 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2912#section=Biological-Test-Results Page: 128.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2912#section=Biological-Test-Results Page: 6.0	yes [IC50 17.8293 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22634058/	yes [IC50 3 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2912#section=Biological-Test-Results Page: 2.0	yes [IC50 5.6381 uM]
CYP1A2 2333	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/22310298/	yes
CYP2A6 911	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/22310298/	yes
CYP2B6 1160	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/22310298/	yes
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/22310298/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2912#section=Biological-Test-Results Page: 199 \| 200	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2912#section=Biological-Test-Results Page: 212.0

PubMed

Title	Date	PubMed
Detection of mutagenic activities of various pesticides in Neurospora crassa.	2003-01	12478420
Induction of sister chromatid exchanges by cypermethrin and carbosulfan in bone marrow cells of mice in vivo.	2003-01	12473735
Determination of active ingredient in synthetic pyrethroid formulations by high-performance thin-layer chromatography/densitometry.	2002-12-13	12477208
Effect of community-wide use of insecticide-treated nets for 3-4 years on malarial morbidity in Tanzania.	2002-12	12460390
Mode of acute action of cypermethrin on peripheral nerves.	2002-11-09	12424749
Monitoring of pesticide residues in Egyptian fruits and vegetables during 1997.	2002-11	12456272
Kinetics of distribution of cypermethrin in blood, brain, and spinal cord after a single administration to rabbits.	2002-11	12375126
Estrogenicity of organophosphorus and pyrethroid pesticides.	2002-10-11	12396874
Investigation of acute toxicity of beta-cypermethrin on guppies Poecilia reticulata.	2002-10	12243328
Determining demographic effects of cypermethrin in the marine copepod Acartia tonsa: stage-specific short tests versus life-table tests.	2002-10	12202935
Enzyme-linked immunosorbent assay for the pyrethroid deltamethrin.	2002-09-25	12236674
Suppression of bloodfeeding by Ochlerotatus dorsalis and Ochlerotatus melanimon on cattle treated with python ear tags.	2002-09	12322943
Dynamics of cypermethrin resistance in the field in the horn fly, Haematobia irritans.	2002-09	12243232
Toxic effects of cypermethrin on certain hematological aspects of fresh water fish Channa punctatus.	2002-09	12177757
Carcinogenic and cocarcinogenic potential of cypermethrin on mouse skin.	2002-08-08	12175521
Pyrethroid exposure of the general population-is this due to diet.	2002-08-05	12191872
Spatiotemporal regulation of moesin phosphorylation and rear release by Rho and serine/threonine phosphatase during neutrophil migration.	2002-08-01	12126963
Cypermethrin induces glutathione S-transferase activity in the shore crab, Carcinus maenas.	2002-08	12206409
Broad-spectrum insecticide resistance in obliquebanded leafroller Choristoneura rosaceana (Lepidoptera: Tortricidae) from Michigan.	2002-08	12192909
Field-simulator studies of insecticide resistance to dimethylcarbamates and pyrethroids conferred by metabolic- and target site-based mechanisms in peach-potato aphids, Myzus persicae (Hemiptera: Aphididae).	2002-08	12192906
Group effects on insecticide toxicity in workers of the Formosan subterranean termite, Coptotermes formosanus Shiraki.	2002-08	12192900
Plant allelochemicals differentially regulate Helicoverpa zea cytochrome P450 genes.	2002-08	12144700
Determination of pyrethroid residues in tobacco and cigarette smoke by capillary gas chromatography.	2002-07-26	12198849
Role of PP2B in cAMP-induced dephosphorylation and translocation of NTCP.	2002-07	12065290
Cypermethrin-induced plasma membrane perturbation on erythrocytes from rats: reduction of fluidity in the hydrophobic core and in glutathione peroxidase activity.	2002-06-14	12049839
[Triatomine: ovicidal action of some pyretroids].	2002-06-05	12045817
Acaricide resistance profiles of single- and multi-host ticks from communal and commercial farming areas in the Eastern Cape and North-West Provinces of South Africa.	2002-06	12234005
Evidence for p-glycoprotein modification of insecticide toxicity in mosquitoes of the Culex pipiens complex.	2002-06	12109718
Comparison of two bioassay techniques for assessing the acute toxicity of pesticides to chironomid larvae (Diptera: Chironomidae).	2002-06	12083354
Toxic effect of single and binary treatments of synthetic and plant-derived molluscicides against Achatina fulica.	2002-05-17	12015802
[Integrated control of main diseases and insects of Dendranthema morifolium].	2002-04	12222051
Pesticide toxicity assessment using an electrochemical biosensor with Pseudomonas putida and a bioluminescence inhibition assay with Vibrio fischeri.	2002-04	12194026
Insecticide susceptibility and detoxication enzyme activities among Coptotermes formosanus Shiraki workers sampled from different locations in New Orleans.	2002-04	11976062
Human blood and environmental media screening method for pesticides and polychlorinated biphenyl compounds using liquid extraction and gas chromatography-mass spectrometry analysis.	2002-03-25	11936688
Immunotoxicological investigation in rats dosed repeatedly with combinations of cypermethrin, As(III), and Hg(II).	2002-03-05	11844615
Multiresidue method for the analysis of multiclass pesticides in agricultural products by gas chromatography-tandem mass spectrometry.	2002-03	11996358
In-season changes in resistance to insecticides in Helicoverpa armigera (Lepidoptera: Noctuidae) in India.	2002-02	11942748
Linkage of genes for sodium channel and cytochrome P450 (CYP6B10) in Heliothis virescens.	2002-02	11852648
Thermal decomposition and isomerization of cis-permethrin and beta-cypermethrin in the solid phase.	2002-02	11852644
Cypermethrin resistance in Angora goat lice?	2002-01-05	11817864
Partitioning, bioavailability, and toxicity of the pyrethroid insecticide cypermethrin in sediments.	2002-01	11808535
Uptake and effects of the cypermethrin-containing sea lice treatment Excis in the marine mussel, Mytilus edulis.	2002	12442804
Mutagenic potential of cypermethrin in mouse dominant lethal assay.	2002	12435079
Physical and chemical properties of pyrethroids.	2002	12132343
Mycorrhizal growth in pure cultures in the presence of pesticides.	2002	12002401
Isolation and identification of synthetic pyrethroid-degrading bacteria.	2002	11872130
Observations on the biology and control of the chewing louse (Bovicola limbata) of Angora goats in Great Britain.	2001-12-01	11765325
Effect of pyrethroids on carbohydrate metabolic pathways in common carp, Cyprinus carpio.	2001-12	11802603
Effects of cypermethrin on antioxidant enzyme activities and lipid peroxidation in liver and kidney of the freshwater fish, Oreochromis niloticus and Cyprinus carpio (L.).	2001-11	11911634
Elucidation of tumor-promoting potential of a combination pesticide by short-term, in vivo bioassay.	2001	11797832

Patents

Sample Use Guides

In Vivo Use Guide

2.5 mg/kg spray at 62.5 ppm

Route of Administration: Topical

In Vitro Use Guide

Application of 200 uM cypermethrin in normal Ringer’s solution to a single nerve preparation immediately increases the threshold interval Vs - Vm until inexcitability of the nerve fiber occurs after about 4 min.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:30:05 GMT 2025` Edited by `admin` on `Mon Mar 31 18:30:05 GMT 2025`
Record UNII	1TR49121NP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CYANO(3-PHENOXYPHENYL)METHYL 3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE

Preferred Name

English

CYPERMETHRIN

Common Name

English

NSC-760420

Code

English

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

Common Name

English

CYPERMETHRIN [ISO]

Common Name

English

CYPERMETHRIN [HSDB]

Common Name

English

CYPERMETHRIN [MI]

Common Name

English

Cypermethrin [WHO-DD]

Common Name

English

(RS)-.ALPHA.-CYANO-3-PHENOXYBENZYL (1RS,3RS)-(1RS,3RS)-3-(2,2-DICHLOROVINYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE

Systematic Name

English

CYPERMETHRIN [MART.]

Common Name

English

Classification Tree Code System Code

WHO-ATC

P03BA02