CYPHENOTHRIN

Details

Stereochemistry	MIXED
Molecular Formula	C24H25NO3
Molecular Weight	375.4602
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)=CC1C(C(=O)OC(C#N)C2=CC(OC3=CC=CC=C3)=CC=C2)C1(C)C

InChI

InChIKey=FJDPATXIBIBRIM-UHFFFAOYSA-N

InChI=1S/C24H25NO3/c1-16(2)13-20-22(24(20,3)4)23(26)28-21(15-25)17-9-8-12-19(14-17)27-18-10-6-5-7-11-18/h5-14,20-22H,1-4H3

HIDE SMILES / InChI

Molecular Formula	C24H25NO3
Molecular Weight	375.4602
Charge	0
Count

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

Description
Sources: http://www.petplace.com/article/drug-library/library/over-the-counter/fipronil-and-cyphenothrin-parastar-plus-for-dogs
Curator's Comment: description was created based on several sources, including http://www.who.int/whopes/quality/en/ddtrans-cyphenothrin_Spec_Eval_Sept_2005.pdf | http://pmep.cce.cornell.edu/profiles/insect-mite/cadusafos-cyromazine/cyphenothrin/cyphenothrin702.pdf | http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1181.htm | http://parasitipedia.net/index.php?option=com_content&view=article&id=2462&Itemid=2729

Cyphenothrin is one of the type II pyrethroid insecticide, in combination with fipronil it used to provide dogs with protection to common topical parasites in dogs. Cyphenothrin primarily affects sodium channels in excitable membranes causing a prolongation of the sodium current during excitation. The prolonged sodium current results in the development of a depolarizing after potential following the action and is responsible for the induction of repetitive activity, which is the most characteristic effect of pyrethroid poisoning in the nervous system. At low concentrations, insects and other arthropods suffer from hyperactivity. At high concentrations, they are paralyzed and die.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
ion gates of the sodium channel of insects 2 Target ID: ion gates of the sodium channel of insects Sources: https://www.toxno.com.au/toxins/substance_id_7379.html	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ectoparasitic infections 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26291751	Curative		Approved 8429	Parastar® Plus Approved Use Unknown

PubMed

Title	Date	PubMed
Chemical composition and biological activity of the volatiles of Anthemis melampodina and Pluchea dioscoridis.	2002 Mar	11933125
Field performance of cyphenothrin: an integrated insecticide strategy against German cockroaches (Dictyoptera: Blatellidae).	2005 Jun	16161703
The status and seasonal changes of organophosphate and pyrethroid resistance in Turkish populations of the house fly, Musca domestica L. (Diptera: Muscidae).	2006 Dec	17249365
Susceptibility of Culex pipiens complex to some insecticides in Qatar.	2007 Dec	18383791
Control of aggregated populations of the eye fly Siphunculina funicola (diptera: chloropidae) using pyrethroid aerosols.	2008 Mar	18564709
Irritability and repellency of synthetic pyrethroids on an Aedes aegypti population from Thailand.	2009 Dec	20836825
Effectiveness of Diflubenzuron in the control of houseflies.	2010 Jun	20539047
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.	2011 Sep 14	21786822

Patents

Sample Use Guides

In Vivo Use Guide

for dogs: The dose of Parastar Plus® (Fipronil mixed with a second ingredient cyphenothrin) and Fiproguard Max® (is the same product as Parastar Plus but by a different manufacturer) is based on the weight of the dog and pipettes are available in 0.67 mL (for dogs from 4 to 22 pounds), 1.34 mL (for dogs 23 to 44 pounds), 2.68 mL (for dogs 45 to 88 pounds) and 4.02 mL (for dogs 89 to 132 pounds). One pipette is applied topically every 30 days. The duration of administration depends on the condition being treated, response to the medication and the development of any adverse effects.

Route of Administration: Oral

In Vitro Use Guide

Experiments were performed using the mouse neuroblastoma cell line NIE-115. Three main effects of the cyphenothrin (25 uM) was found: (1) the peak amplitude of the sodium current increased; (2) the declining phase of the sodium current during depolarization was greatly slowed down resuilting in a marked residual current towards the end of tlhe 15 ms pulse; and (3) after repolarization of the membrane to the holding potential a large, slowly decaying sodium tail current remained.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:27:04 GMT 2023` Edited by `admin` on `Sat Dec 16 05:27:04 GMT 2023`
Record UNII	S0IU5Y1R32
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CYPHENOTHRIN

Common Name

English

CYPHENOTHRIN [MI]

Common Name

English

S-2703

Code

English

D.D-T-CYPHENOTHRIN [JAN]

Common Name

English

.ALPHA.-CYANO-M-PHENOXYBENZYL 2,2-DIMETHYL-3-(2-METHYLPROPENYL)CYCLOPROPANECARBOXYLATE

Systematic Name

English

2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)CYCLOPROPANE CARBOXYLIC ACID CYANO(3-PHENOXYPHENYL)METHYL ESTER

Systematic Name

English

GOKILAHT

Brand Name

English

S-2703 FORTE

Code

English

CHIFENOTHRINE

Common Name

English

.ALPHA.-CYANO-3-PHENOXYBENZYL CHRYSANTHEMATE

Common Name

English

CYPHENOTHRIN [ISO]

Common Name

English

CYANO-3-PHENOXYBENZYL 2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)CYCLOPROPANECARBOXYLATE

Systematic Name

English

CYCLOPROPANECARBOXYLIC ACID, 2,2-DIMETHYL-3-(2-METHYL-1-PROPEN-1-YL)-, CYANO(3-PHENOXYPHENYL)METHYL ESTER

Common Name

English

D.D-T-CYPHENOTHRIN

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

129013