FLURALANER

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=CC(=CC=C1C(=O)NCC(=O)NCC(F)(F)F)C2=NOC(C2)(C3=CC(Cl)=CC(Cl)=C3)C(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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
UniProt: V9ZAE7 (GABA-gated chloride channel) 1	Inhibitor 8,504		1.6 nM [IC50]
UniProt: V9ZCF2 (GABA-gated chloride channel rdl-S285) 1	Inhibitor 8,504		0.45 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Flea infestations 12	Curative		Approved 8,583	Bravecto
Tick infestations 4	Curative		Approved 8,583	Bravecto

PubMed

Show entries

Title	Date	PubMed
The antiparasitic isoxazoline A1443 is a potent blocker of insect ligand-gated chloride channels.	2010 Jan 1	19944072
A randomized, blinded, controlled USA field study to assess the use of fluralaner tablets in controlling canine flea infestations.	2014 Aug 16	25129395
The novel isoxazoline ectoparasiticide fluralaner: selective inhibition of arthropod γ-aminobutyric acid- and L-glutamate-gated chloride channels and insecticidal/acaricidal activity.	2014 Feb	24365472
Fluralaner, a novel isoxazoline, prevents flea (Ctenocephalides felis) reproduction in vitro and in a simulated home environment.	2014 Jun 19	24946811
Safety of the concurrent treatment of dogs with Bravecto (fluralaner) and Scalibor protectorband (deltamethrin).	2014 Mar 19	24646450

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Sample Use Guides

In Vivo Use Guide

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

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
Record UNII	WSH8393RM5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLURALANER

Official Name

English

fluralaner [INN]

Preferred 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

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Code