Fluralaner

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Fluralaner
Clinical data
Pronunciation/ˌflʊərəˈlænər/ FLOOR-ə-LAN-ər
Trade namesBravecto
Other names
  • A1443, AH252723
  • 4-[(5RS)-5-(3,5-Dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-1,2-oxazol-3-yl]-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]-o-toluamide
Routes of
administration		By mouth (chewable tablets)
ATCvet code
Legal status
Legal status
Pharmacokinetic data
Bioavailability20–27%;[1] reduced in the fasted state[2]
Elimination half-life9.3–16.2 days[3]
Identifiers
  • (±)-4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]-2-methyl-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.215.812 Edit this at Wikidata
Chemical and physical data
FormulaC22H17Cl2F6N3O3
Molar mass556.29 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • Cc1cc(ccc1C(=O)NCC(=O)NCC(F)(F)F)C2=NOC(C2)(c3cc(cc(c3)Cl)Cl)C(F)(F)F
  • InChI=1S/C22H17Cl2F6N3O3/c1-11-4-12(2-3-16(11)19(35)31-9-18(34)32-10-21(25,26)27)17-8-20(36-33-17,22(28,29)30)13-5-14(23)7-15(24)6-13/h2-7H,8-10H2,1H3,(H,31,35)(H,32,34)
  • Key:MLBZKOGAMRTSKP-UHFFFAOYSA-N

Fluralaner (INN)[4] is a systemic insecticide and acaricide that is administered orally.[5] The U.S. Food and Drug Administration (FDA) approved it under the trade name Bravecto for flea treatment in dogs in May 2014.[6] The EU approved the drug in February 2014.[7] Australia approved it for the treatment and prevention of ticks and fleas on dogs in January 2015.[8]

Mode of action

Fluralaner inhibits γ-aminobutyric acid (GABA)-gated chloride channels (GABAA receptors) and L-glutamate-gated chloride channels (GluCls).[9] Potency of fluralaner is comparable to fipronil (a related GABA-antagonist insecticide and acaricide).[10]

See also

References

  1. ^ a b "Bravecto (fluralaner) for the Treatment and Prophylaxis of Arachnoenthomoses in Dogs. Full Prescribing Information" (PDF) (in Russian). Intervet GesmbH. Retrieved 14 November 2016.
  2. ^ Walther, FM; Allan, MJ; Roepke, RKA; Nuernberger, MC (2014). "The Effect of Food on the Pharmacokinetics of Oral Fluralaner in Dogs". Parasites & Vectors. 7 (1): 84. doi:10.1186/1756-3305-7-84. PMC 3975707. PMID 24598049.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  3. ^ "Bravecto (fluralaner) Flavored Chews for Dogs. Prescribing Information" (PDF). Intervet, Inc., a subsidiary of Merck & Company, In. Retrieved 14 November 2016.
  4. ^ "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 69" (PDF). WHO Drug Information. 27 (1): 59. 2013. Retrieved 14 November 2016.
  5. ^ Walther, FM; Allan, MJ; Roepke, RKA; Nuernberger, MC (2014). "Safety of Fluralaner Chewable Tablets (Bravecto™), a Novel Systemic Antiparasitic Drug, in Dogs After Oral Administration". Parasites & Vectors. 7 (1): 87. doi:10.1186/1756-3305-7-87. PMC 3975339. PMID 24606886.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  6. ^ Lee, J (21 May 2014). "New Flea/Tick Medication by Merck Just Approved: Bravecto". Retrieved 3 November 2014.
  7. ^ "MSD Animal Health receives EU approval for Bravecto". 19 February 2014. Retrieved 3 Nov 2014.
  8. ^ "Agricultural and Veterinary Chemicals" (PDF). Australian Pesticides and Veterinary Medicines Authority. 10 February 2015. Retrieved 14 February 2019.
  9. ^ Gassel, M; Wolf, C; Noack, S; Williams, H; Ilg, T (February 2014). "The Novel Isoxazoline Ectoparasiticide Fluralaner: Selective Inhibition of Arthropod γ-Aminobutyric Acid- and L-Glutamate-gated Chloride Channels and Insecticidal/Acaricidal Activity". Insect Biochemistry and Molecular Biology. 45: 111–24. doi:10.1016/j.ibmb.2013.11.009. PMID 24365472.
  10. ^ Asahi, M; Kobayashi, M; Matsui, H; Nakahira, K (January 2015). "Differential Mechanisms of Action of the Novel γ-Aminobutyric Acid Receptor Antagonist Ectoparasiticides Fluralaner (A1443) and Fipronil". Pest Management Science. 71 (1): 91–5. doi:10.1002/ps.3768. PMID 24591229.
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