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Metaflumizone

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.

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
  • 139968-49-3
ChemSpider
  • 16738643
UNII
  • 71I50E2UDI
CompTox Dashboard (EPA)
  • DTXSID6040373
ECHA InfoCard100.107.480
Chemical and physical data
FormulaC24H16F6N4O2
Molar mass506.408 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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

Similar insecticides edit

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 edit

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 edit

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 edit

  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.

External links edit

  • Metaflumizone in the Pesticide Properties DataBase (PPDB)

metaflumizone, semicarbazone, insecticide, indicated, veterinary, treatment, fleas, ticks, marketed, under, brand, name, promeris, discontinued, variant, promeris, called, promeris, promeris, dogs, indicated, canine, formulated, blend, metaflumizone, amitraz, . 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 MetaflumizoneClinical dataTrade namesProMeris AlverdeATCvet codeQP53AX25 WHO IdentifiersIUPAC name EZ 2 2 4 Cyanophenyl 1 3 trifluoromethyl phenyl ethylidene N 4 trifluoromethoxy phenyl hydrazinecarboxamideCAS Number139968 49 3ChemSpider16738643UNII71I50E2UDICompTox Dashboard EPA DTXSID6040373ECHA InfoCard100 107 480Chemical and physical dataFormulaC 24H 16F 6N 4O 2Molar mass506 408 g mol 13D model JSmol Interactive imageSMILES FC F F Oc1ccc cc1 NC O N N C Cc2ccc C N cc2 c3cccc c3 C F F FInChI 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 Contents 1 Similar insecticides 2 Action 3 Adverse effects reported 4 References 5 External linksSimilar insecticides editMetaflumizone 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 editMetaflumizone 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 editIn 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 edit Metaflumizone ProMeris and ProMeris Duo for Dogs and Cats PetPlace Drug Library 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 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 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 External links editMetaflumizone in the Pesticide Properties DataBase PPDB Retrieved from https en wikipedia org w index php title Metaflumizone amp oldid 1135160575, wikipedia, wiki, book, books, library,

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