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Metaflumizone

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Metaflumizone
Clinical data
Trade namesProMeris, Alverde
ATCvet code
Identifiers
  • (EZ)-2-{2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene} -N-[4-(trifluoromethoxy)phenyl]hydrazinecarboxamide
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.107.480 Edit this at Wikidata
Chemical and physical data
FormulaC24H16F6N4O2
Molar mass506.408 g·mol−1
3D model (JSmol)
  • FC(F)(F)Oc1ccc(cc1)NC(=O)N\N=C(\Cc2ccc(C#N)cc2)c3cccc(c3)C(F)(F)F
  • 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

Metaflumizone is a semicarbazone insecticide indicated 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.[1] The metaflumizone-only formulation is waterproof and typically remain effective for 30–45 days in a cutaneous application at the base of the neck.

Similar insecticides

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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.[2]

Action

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Metaflumizone 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.[2] The toxin has been tested for efficacy against Spodoptera eridania moths[2] 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.[3] 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

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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.[4]

References

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  1. ^ "Metaflumizone (ProMeris and ProMeris Duo) for Dogs and Cats". PetPlace Drug Library.
  2. ^ a b c Salgado VL, Hayashi JH (December 2007). "Metaflumizone is a novel sodium channel blocker insecticide". Veterinary Parasitology. 150 (3): 182–9. doi:10.1016/j.vetpar.2007.08.032. PMID 17959312.
  3. ^ Bouhsira E, Fysikopoulos A, Franc M (August 2009). "Efficacy of fipronil-(S)-methoprene, metaflumizone combined with amitraz, and pyriprole commercial spot-on products in preventing Culex pipiens pipiens from feeding on dogs". The Veterinary Record. 165 (5): 135–7. doi:10.1136/vr.165.5.135. PMID 19648637.
  4. ^ Tremayne J (18 April 2011). "Study Links ProMeris to Pemphigus Foliaceus; Pfizer Stopping Its Production". Veterinary Practice News. California, United States: BowTie. Retrieved 26 April 2011.
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