Flumethrin

Structural formula
	Mixture of several stereoisomers - structural formula without absolute configuration
General
Non-proprietary name	Flumethrin
other names	α-Cyano (4-fluoro-3-phenoxy) benzyl-3- [2-chloro-2- (4-chlorophenyl) ethenyl] -2,2-dimethylcyclopropanecarboxylate ( IUPAC )
Molecular formula	C 28 H 22 Cl 2 FNO 3
External identifiers / databases
EC number	274-110-4
ECHA InfoCard	100,067,352
PubChem	6033664
ChemSpider	4785776
Wikidata	Q425958
Drug information
ATC code	Q P53AC05
Drug class	Pyrethroid - insecticide
Mechanism of action	Opening of the Na + channels
properties
Molar mass	510.39 g · mol -1
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 301 + 311 + 331-315-317-319
	P: 261-280-301 + 310-305 + 351 + 338-311
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Flumethrin is an active ingredient from the group of type II pyrethroids . It is used externally in veterinary medicine as an antiparasitic against insects and ticks . Flumethrin opens the sodium channels of nerve cells in parasites, causing overexcitation and ultimately death.

Isomerism

Flumethrin is a complex mixture of isomers . The molecule contains three asymmetrically substituted carbon atoms, there is a cis - trans isomerism on the cyclopropane ring and another cis - trans isomerism on the carbon-carbon double bond of the alkene . So there are 16 different isomers. Commercial flumethrin contains as an active ingredient

92% of the isomers with trans geometry on the cyclopropane ring and cis arrangement on the olefinic carbon-carbon double bond as well
8% of the isomers with cis geometry on the cyclopropane ring and cis arrangement on the olefinic carbon-carbon double bond.

Since these isomers are each present as a racemate , a mixture of four isomers is used in practice, the different effectiveness of which has been proven experimentally in part.

Trade names

Bayticol (ad usum veterinarium) , Bayvarol (ad usum veterinarium) against the Varroa mite , Kiltix (combination with Propoxur ), Seresto (combination with Imidacloprid )

Web links

Entry on Flumethrin at Vetpharm

Individual evidence

↑ ^a ^b Flumethrin data sheet from Sigma-Aldrich , accessed on May 15, 2017 ( PDF ).

↑ Flumethrin: Summary of Characteristics for flumethrin, as of June 1, 1998 on the European Medicines Agency EMEA website (PDF, 68.1 kB), accessed July 30, 2009.

↑ ^a ^b H. J. Schnitzerling, J. Nolan, S. Hughes: Toxicology and Metabolism of Isomers of Flumethrin in Larvae of Pyrethroid-Susceptilble and Resistant Strains of the Cattle Tick Boophilus microplus (Acari: Ixodidae). In: Experimental & Applied Acarology. 6, 1989, pp. 47-54. PMID 2707107 .

[Sigma-1] Flumethrin data sheet from Sigma-Aldrich , accessed on May 15, 2017 ( PDF ).

[Flumethrin-2] Flumethrin: Summary of Characteristics for flumethrin, as of June 1, 1998 on the European Medicines Agency EMEA website (PDF, 68.1 kB), accessed July 30, 2009.

[Schnitzerling-3] H. J. Schnitzerling, J. Nolan, S. Hughes: Toxicology and Metabolism of Isomers of Flumethrin in Larvae of Pyrethroid-Susceptilble and Resistant Strains of the Cattle Tick Boophilus microplus (Acari: Ixodidae). In: Experimental & Applied Acarology. 6, 1989, pp. 47-54. PMID 2707107 .