Details
Stereochemistry | RACEMIC |
Molecular Formula | C22H17Cl2F6N3O3 |
Molecular Weight | 556.285 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(C=CC(=C1)C2=NOC(C2)(C3=CC(Cl)=CC(Cl)=C3)C(F)(F)F)C(=O)NCC(=O)NCC(F)(F)F
InChI
InChIKey=MLBZKOGAMRTSKP-UHFFFAOYSA-N
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)
Molecular Formula | C22H17Cl2F6N3O3 |
Molecular Weight | 556.285 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Fluralaner, isoxazoline class compound, is a systemic insecticide and acaricide with antiparasitic activity against cat and dog fleas and ticks. Fluralaner is an inhibitor of the arthropod nervous system. Fluralaner inhibits γ-aminobutyric acid (GABA)-gated chloride channels (GABACls) and L-glutamate-gated chloride channels (GluCls). Potency of fluralaner is comparable to fipronil (a phenylpyrazole ectoparasiticide). The U.S. Food and Drug Administration (FDA) approved it under the trade name Bravecto for flea and tick treatment and prevention in dogs in May 2014. Bravecto kills adult fleas and is indicated for the treatment and prevention of flea infestations (Ctenocephalides felis) and the treatment and control of tick infestations [Ixodes scapularis (black-legged tick), Dermacentor variabilis (American dog tick), and Rhipicephalus sanguineus (brown dog tick)] in dogs and puppies 6 months of age and older. Bravecto is also indicated for the treatment and control of Amblyomma americanum (lone star tick) infestations in dogs and puppies 6 months of age and older.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24404981 | https://www.ncbi.nlm.nih.gov/pubmed/23465072
Curator's Comment: Known to be CNS penetrant in insects. Human data not available
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: UniProt: V9ZAE7 (GABA-gated chloride channel) |
1.6 nM [IC50] | ||
Target ID: UniProt: V9ZCF2 (GABA-gated chloride channel rdl-S285) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24365472 |
0.45 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | Bravecto Approved UseIndicated for the treatment and prevention of flea infestations (Ctenocephalides felis), and the treatment and control of tick infestations [Ixodes scapularis (black-legged tick), Dermacentor variabilis (American dog tick), and Rhipicephalus sanguineus (brown dog tick)] for 12 weeks in dogs and puppies 6 months of age and older, and weighing 4.4 pounds or greater. Is also indicated for the treatment and control of Amblyomma americanum (lone star tick) infestations for 8 weeks in dogs and puppies 6 months of age and older, and weighing 4.4 pounds or greater. Launch Date2014 |
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Curative | Bravecto Approved UseIndicated for the treatment and prevention of flea infestations (Ctenocephalides felis), and the treatment and control of tick infestations [Ixodes scapularis (black-legged tick), Dermacentor variabilis (American dog tick), and Rhipicephalus sanguineus (brown dog tick)] for 12 weeks in dogs and puppies 6 months of age and older, and weighing 4.4 pounds or greater. Is also indicated for the treatment and control of Amblyomma americanum (lone star tick) infestations for 8 weeks in dogs and puppies 6 months of age and older, and weighing 4.4 pounds or greater. Launch Date2014 |
PubMed
Title | Date | PubMed |
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The antiparasitic isoxazoline A1443 is a potent blocker of insect ligand-gated chloride channels. | 2010 Jan 1 |
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A randomized, blinded, controlled USA field study to assess the use of fluralaner tablets in controlling canine flea infestations. | 2014 Aug 16 |
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The novel isoxazoline ectoparasiticide fluralaner: selective inhibition of arthropod γ-aminobutyric acid- and L-glutamate-gated chloride channels and insecticidal/acaricidal activity. | 2014 Feb |
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Fluralaner, a novel isoxazoline, prevents flea (Ctenocephalides felis) reproduction in vitro and in a simulated home environment. | 2014 Jun 19 |
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Safety of the concurrent treatment of dogs with Bravecto (fluralaner) and Scalibor protectorband (deltamethrin). | 2014 Mar 19 |
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A randomized, blinded, controlled and multi-centered field study comparing the efficacy and safety of Bravecto (fluralaner) against Frontline (fipronil) in flea- and tick-infested dogs. | 2014 Mar 4 |
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The effect of food on the pharmacokinetics of oral fluralaner in dogs. | 2014 Mar 5 |
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Safety of fluralaner, a novel systemic antiparasitic drug, in MDR1(-/-) Collies after oral administration. | 2014 Mar 6 |
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Safety of fluralaner chewable tablets (Bravecto), a novel systemic antiparasitic drug, in dogs after oral administration. | 2014 Mar 7 |
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Pharmacokinetics of fluralaner in dogs following a single oral or intravenous administration. | 2014 Mar 7 |
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The speed of kill of fluralaner (Bravecto™) against Ixodes ricinus ticks on dogs. | 2014 Nov 18 |
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Safety of concurrent treatment of dogs with fluralaner (Bravecto™) and milbemycin oxime-praziquantel. | 2014 Oct 15 |
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Differential mechanisms of action of the novel γ-aminobutyric acid receptor antagonist ectoparasiticides fluralaner (A1443) and fipronil. | 2015 Jan |
Sample Use Guides
Administered topically as a single dose every 12 weeks to provide a minimum dose of 11.4 mg/lb (25 mg/kg) body weight.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19944072
Two-electrode voltage clamp electrophysiology was used to confirm that A1443 blocks GABA- and glutamate-induced chloride currents in Xenopus oocytes expressing MdGBCl or MdGluCl channels, with IC50 values of 5.32 and 79.9 nM, respectively.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 04:18:36 GMT 2023
by
admin
on
Sat Dec 16 04:18:36 GMT 2023
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Record UNII |
WSH8393RM5
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QP53BX05
Created by
admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
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EMA VETERINARY ASSESSMENT REPORTS |
BRAVECTO [AUTHORISED]
Created by
admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
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CFR |
21 CFR 524.998
Created by
admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
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CFR |
21 CFR 520.998
Created by
admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
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EMA VETERINARY ASSESSMENT REPORTS |
BRAVECTO [AUTHORISED]
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admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
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864731-61-3
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Fluralaner
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WSH8393RM5
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25144319
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fluralaner
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300000023784
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9485
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1538098
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m11901
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ZZ-130
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WSH8393RM5
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DTXSID90235581
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C169997
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CHEMBL2364610
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE |
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ACTIVE MOIETY |