Structure via PubChem · Public domain (PubChem)
afoxolaner
Sign in to saveAfoxolaner is an insecticide and acaricide that belongs to the isoxazoline chemical compound group. It is used to kill fleas and ticks in small animals. ==Mechanism== Alfoxolander is a GABA receptor antagonist, which stops chloride transmission in nerves and muscles resulting in paralysis with the paralysis resulting in death for the insect. Alfoxolaner is more selective for GABA repectors in insects than mammals making it safe to give to an animal in amounts that are still lethal to insects.
Chemical data
- Formula
- C26H17ClF9N3O3
- Molecular weight
- 625.9 g/mol
- IUPAC name
- 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]naphthalene-1-carboxamide
- SMILES
- C1C(=NOC1(C2=CC(=CC(=C2)Cl)C(F)(F)F)C(F)(F)F)C3=CC=C(C4=CC=CC=C43)C(=O)NCC(=O)NCC(F)(F)F
- InChIKey
- OXDDDHGGRFRLEE-UHFFFAOYSA-N
- XLogP
- 6.7
- Polar surface area
- 79.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 625.081
- Has use
- acaricide
Show 3 more facts
- chemical formula
- C₂₆H₁₇ClF₉N₃O₃
- Commons category
- Afoxolaner
- canonical SMILES
- C1C(=NOC1(C2=CC(=CC(=C2)Cl)C(F)(F)F)C(F)(F)F)C3=CC=C(C4=CC=CC=C43)C(=O)NCC(=O)NCC(F)(F)F
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Mechanism
- Use
- Legal status
- Brand names
- References
Afoxolaner is an insecticide and acaricide that belongs to the isoxazoline chemical compound group. It is used to kill fleas and ticks in small animals. ==Mechanism== Alfoxolander is a GABA receptor antagonist, which stops chloride transmission in nerves and muscles resulting in paralysis with the paralysis resulting in death for the insect. Alfoxolaner is more selective for GABA repectors in insects than mammals making it safe to give to an animal in amounts that are still lethal to insects.
Selectivity for insect over mammalian GABA-receptors has been demonstrated for other isoxazolines. The selectivity might be explained by the number of pharmacological differences that exist between GABA-gated chloride channels of insects and vertebrates. ==Use== Afoxolaner is given orally and is then rapidly distributed into the systemic circulation, when a tick or flea feeds on the blood of the host it ingests the afoxolaner and becomes paralysed. Thus fleas and ticks must first feed on the host for the drug to be effective. Afoxolaner has been given up to five times the therapeutic dose without causing intoxication. == Legal status == The marketing authorization was granted by the European Medicines Agency in February 2014, for Nexgard, and in January 2015, for Nexgard Spectra.
Excerpted from Wikipedia’s “afoxolaner” article, available under the CC BY-SA 4.0 licence.