Afoxolaner

Afoxolaner (INN) is an insecticide and acaricide that belongs to the isoxazoline chemical compound group.

Afoxolaner
Clinical data
Pronunciation/eɪˌfɒksoʊˈlænər/ ay-FOK-soh-LAN-ər
Trade namesNexgard, Frontpro
Other names4-[(5RS)-5-(5-Chloro-α,α,α-trifluoro-m-tolyl)-4,5-dihydro-5-(trifluoromethyl)-1,2-oxazol-3-yl]-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]naphthalene-1-carboxamide
License data
Routes of
administration		By mouth
ATCvet code
Legal status
Legal status
  • CA: ℞-only
  • US: ℞-only
  • EU: Rx-only
  • OTC (RU)
Pharmacokinetic data
Bioavailability74% (Tmax = 2–4 hours)
Elimination half-life14 hours
ExcretionBile duct (major route)
Identifiers
  • 4-{5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl}-N-{2-oxo-2-[(2,2,2- trifluoroethyl)amino]ethyl}naphthalene-1-carboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.267.822
Chemical and physical data
FormulaC26H17ClF9N3O3
Molar mass625.88 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • FC(F)(F)CNC(=O)CNC(=O)c1ccc(C2=NOC(C2)(c3cc(Cl)cc(c3)C(F)(F)F)C(F)(F)F)c4ccccc14
  • InChI=1S/C26H17ClF9N3O3/c27-15-8-13(7-14(9-15)25(31,32)33)23(26(34,35)36)10-20(39-42-23)18-5-6-19(17-4-2-1-3-16(17)18)22(41)37-11-21(40)38-12-24(28,29)30/h1-9H,10-12H2,(H,37,41)(H,38,40)
  • Key:OXDDDHGGRFRLEE-UHFFFAOYSA-N

It acts as an antagonist at GABA-receptors (those gated by the neurotransmitter gamma-aminobutyric acid) and other ligand-gated chloride channels. Isoxazolines, among the chloride channel modulators, bind to a distinct and unique target site within the insect GABA-gated chloride channels, thereby blocking pre-and post-synaptic transfer of chloride ions across cell membranes. Prolonged afoxolaner-induced hyperexcitation results in uncontrolled activity of the central nervous system and death of insects and acarines.

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