Metaflumizone

Metaflumizone is a semicarbazone broad-spectrum insecticide developed by Nihon Nohyaku with activity on Lepidoptera, Coleoptera, and certain Hemiptera.^[1] It is also used for the veterinary treatment of fleas and ticks, marketed under the brand name ProMeris. A discontinued variant of ProMeris, called ProMeris Duo or Promeris for Dogs, was indicated for canine use and was a formulated blend of metaflumizone and amitraz.^[2] The metaflumizone-only formulation is waterproof and typically remain effective for 30–45 days in a cutaneous application at the base of the neck.

Metaflumizone

Clinical data
Trade names	ProMeris, Alverde
ATCvet code	QP53AX25 (WHO)
Identifiers
IUPAC name (EZ)-2-{2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene} -N-[4-(trifluoromethoxy)phenyl]hydrazinecarboxamide
CAS Number	139968-49-3
ChemSpider	16738643
UNII	71I50E2UDI
CompTox Dashboard (EPA)	DTXSID6040373
ECHA InfoCard	100.107.480
Chemical and physical data
Formula	C24H16F6N4O2
Molar mass	506.408 g·mol−1
3D model (JSmol)	Interactive image
SMILES FC(F)(F)Oc1ccc(cc1)NC(=O)N\N=C(\Cc2ccc(C#N)cc2)c3cccc(c3)C(F)(F)F
InChI InChI=1S/C24H16F6N4O2/c25-23(26,27)18-3-1-2-17(13-18)21(12-15-4-6-16(14-31)7-5-15)33-34-22(35)32-19-8-10-20(11-9-19)36-24(28,29)30/h1-11,13H,12H2,(H2,32,34,35) Key:MIFOMMKAVSCNKQ-UHFFFAOYSA-N

Similar insecticides

Metaflumizone is chemically similar to pyrazoline sodium channel blocker insecticides (SCBIs) discovered at Philips-Duphar in the early 1970s, but is less dangerous to mammals than earlier compounds.^[3]

Action

Metaflumizone belongs to IRAC group 22B and works by blocking sodium channels in target insects, resulting in flaccid paralysis. Metaflumizone blocks sodium channels by binding selectively to the slow-inactivated state, which is characteristic of the SCBIs.^[3] The toxin has been tested for efficacy against Spodoptera eridania moths^[3] and is indicated for control of fleas and ticks. However, in a cross comparison with other veterinary flea control substances, Metaflumizone was not shown to result in a significant reduction in the number of engorged adult female Culex mosquitoes.^[4] Therefore, its usefulness as a heartworm control treatment is likely to be insignificant when compared with comparable treatments such as selamectin that do impact the mosquito disease vector.

Adverse effects reported

In 2011, Pfizer Animal Care decided to cease production of the drug based on findings which linked its use to an elevated incidence of the autoimmune disorder pemphigus foliaceus.^[5]