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

Structure Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19944072 | https://www.ncbi.nlm.nih.gov/pubmed/24606886 | https://www.ncbi.nlm.nih.gov/pubmed/24365472 | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b4181fa7-e45f-4beb-a3f5-49c987d584ac

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 Target ID: UniProt: V9ZAE7 (GABA-gated chloride channel) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24365472 \| https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b4181fa7-e45f-4beb-a3f5-49c987d584ac	Inhibitor 8297		1.6 nM [IC50]
UniProt: V9ZCF2 (GABA-gated chloride channel rdl-S285) 1 Target ID: UniProt: V9ZCF2 (GABA-gated chloride channel rdl-S285) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24365472	Inhibitor 8297		0.45 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Flea infestations 12 Sources: https://us.bravecto.com/pdfs/bravecto_pi_mah.pdf	Curative		Approved 8429	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
Tick infestations 4 Sources: https://us.bravecto.com/pdfs/bravecto_pi_mah.pdf	Curative		Approved 8429	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

Title	Date	PubMed
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
Safety of concurrent treatment of dogs with fluralaner (Bravecto™) and milbemycin oxime-praziquantel.	2014 Oct 15	25315498

Patents

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.

Name

Type

Language

FLURALANER

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