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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
Structure of FLURALANER

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)

HIDE SMILES / InChI

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

Curator's Comment: Known to be CNS penetrant in insects. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.6 nM [IC50]
Target ID: UniProt: V9ZCF2 (GABA-gated chloride channel rdl-S285)
0.45 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Bravecto

Approved Use

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)] 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 Date

2014
Curative
Bravecto

Approved Use

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)] 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 Date

2014
PubMed

PubMed

TitleDatePubMed
The antiparasitic isoxazoline A1443 is a potent blocker of insect ligand-gated chloride channels.
2010 Jan 1
A randomized, blinded, controlled USA field study to assess the use of fluralaner tablets in controlling canine flea infestations.
2014 Aug 16
The novel isoxazoline ectoparasiticide fluralaner: selective inhibition of arthropod γ-aminobutyric acid- and L-glutamate-gated chloride channels and insecticidal/acaricidal activity.
2014 Feb
Fluralaner, a novel isoxazoline, prevents flea (Ctenocephalides felis) reproduction in vitro and in a simulated home environment.
2014 Jun 19
Safety of the concurrent treatment of dogs with Bravecto (fluralaner) and Scalibor protectorband (deltamethrin).
2014 Mar 19
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
The effect of food on the pharmacokinetics of oral fluralaner in dogs.
2014 Mar 5
Safety of fluralaner, a novel systemic antiparasitic drug, in MDR1(-/-) Collies after oral administration.
2014 Mar 6
Safety of fluralaner chewable tablets (Bravecto), a novel systemic antiparasitic drug, in dogs after oral administration.
2014 Mar 7
Pharmacokinetics of fluralaner in dogs following a single oral or intravenous administration.
2014 Mar 7
The speed of kill of fluralaner (Bravecto™) against Ixodes ricinus ticks on dogs.
2014 Nov 18
Safety of concurrent treatment of dogs with fluralaner (Bravecto™) and milbemycin oxime-praziquantel.
2014 Oct 15
Differential mechanisms of action of the novel γ-aminobutyric acid receptor antagonist ectoparasiticides fluralaner (A1443) and fipronil.
2015 Jan
Patents

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
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 Sat Dec 16 04:18:36 GMT 2023
Edited
by admin
on Sat Dec 16 04:18:36 GMT 2023
Record UNII
WSH8393RM5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLURALANER
INN   USAN  
USAN   INN  
Official Name English
fluralaner [INN]
Common Name English
4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}benzamide
Systematic Name English
FLURALANER [MI]
Common Name English
BENZAMIDE, 4-(5-(3,5-DICHLOROPHENYL)-4,5-DIHYDRO-5-(TRIFLUOROMETHYL)-3-ISOXAZOLYL)-2-METHYL-N-(2-OXO-2-((2,2,2-TRIFLUOROETHYL)AMINO)ETHYL)- (2) 4-(5-(3,5-DICHLOROPHENYL)-5-(TRIFLUOROMETHYL)-4,5-DIHYDRO-1,2-OXAZOL-3-YL)-2-METHYL-N-(2-OXO-2-((2,2,2-TRIFLUO
Systematic Name English
A-1443
Code English
FLURALANER, (±)-
Common Name English
AH-252723
Code English
FLURALANER (EMA EPAR: VETERINARY)
Common Name English
BRAVECTO
Brand Name English
FLURALANER [USAN]
Common Name English
(±)-FLURALANER
Systematic Name English
FLURALANER [GREEN BOOK]
Common Name English
Classification Tree Code System Code
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
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
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
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
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
Code System Code Type Description
CAS
864731-61-3
Created by admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
PRIMARY
WIKIPEDIA
Fluralaner
Created by admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
PRIMARY
DAILYMED
WSH8393RM5
Created by admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
PRIMARY
PUBCHEM
25144319
Created by admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
PRIMARY
ALANWOOD
fluralaner
Created by admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
PRIMARY
SMS_ID
300000023784
Created by admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
PRIMARY
INN
9485
Created by admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
PRIMARY
RXCUI
1538098
Created by admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m11901
Created by admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
PRIMARY
USAN
ZZ-130
Created by admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
PRIMARY
FDA UNII
WSH8393RM5
Created by admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID90235581
Created by admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
PRIMARY
NCI_THESAURUS
C169997
Created by admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
PRIMARY
ChEMBL
CHEMBL2364610
Created by admin on Sat Dec 16 04:18:36 GMT 2023 , Edited by admin on Sat Dec 16 04:18:36 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY