AFOXOLANER

Details

Stereochemistry	RACEMIC
Molecular Formula	C26H17ClF9N3O3
Molecular Weight	625.87
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC(F)(F)CNC(=O)CNC(=O)C1=C2C=CC=CC2=C(C=C1)C3=NOC(C3)(C4=CC(=CC(Cl)=C4)C(F)(F)F)C(F)(F)F

InChI

InChIKey=OXDDDHGGRFRLEE-UHFFFAOYSA-N

InChI=1S/C26H17ClF9N3O3/c27-15-8-13(7-14(9-15)25(31,32)33)23(26(34,35)36)10-20(39-42-23)18-5-6-19(17-4-2-1-3-16(17)18)22(41)37-11-21(40)38-12-24(28,29)30/h1-9H,10-12H2,(H,37,41)(H,38,40)

HIDE SMILES / InChI

Molecular Formula	C26H17ClF9N3O3
Molecular Weight	625.87
Charge	0
Count

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

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a668d223-47a3-46b7-b642-f2de0dca6ab5 | https://www.ncbi.nlm.nih.gov/pubmed/24631502

Afoxolaner (brand name NexGard) is a member of an isoxazoline class of compounds, which is used to kill adult fleas and is indicated for the treatment and prevention of flea infestations, and the treatment and control of Black-legged tick, American Dog tick, Lone Star tick, and Brown dog tick infestations in dogs and puppies. Afoxolaner is a member of the isoxazoline family, shown to bind at a binding site to inhibit insect and acarine ligand-gated chloride channels, in particular those gated by the neurotransmitter gamma-aminobutyric acid (GABA), thereby blocking pre- and post-synaptic transfer of chloride ions across cell membranes. Afoxolaner blocks native and expressed insect GABA-gated chloride channels with nanomolar potency. Prolonged afoxolaner-induced hyperexcitation results in uncontrolled activity of the central nervous system and death of insects and acarines.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
insect and acarine GABA-gated chloride channels 1 Target ID: insect and acarine GABA-gated chloride channels Sources: https://www.ncbi.nlm.nih.gov/pubmed/24631502	Blocker 537

Conditions

Condition	Modality	Targets	Highest Phase	Product
Flea infestations 12 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a668d223-47a3-46b7-b642-f2de0dca6ab5	Curative		Approved 8429	NEXGARD Approved Use Unknown
Black-legged tick infestations 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a668d223-47a3-46b7-b642-f2de0dca6ab5	Curative		Approved 8429	NEXGARD Approved Use Unknown

PubMed

Title	Date	PubMed
Afoxolaner against fleas: immediate efficacy and resultant mortality after short exposure on dogs.	2014	25148564
Evaluation of the efficacy of afoxolaner against Haemaphysalis longicornis on dogs.	2014 Apr 2	24629429
Evaluation of the efficacy of monthly oral administration of afoxolaner plus milbemycin oxime (NexGard Spectra(®), Merial) in the prevention of adult Spirocerca lupi establishment in experimentally infected dogs.	2016 Aug 15	27514901

Patents

Sample Use Guides

In Vivo Use Guide

in veterinary: NexGard is given orally once a month, at the minimum dosage of 1.14 mg/lb (2.5 mg/kg). Dosing Schedule: Body Weight Afoxolaner Per Chewable (mg) Chewables Administered 4.0 to 10.0 lbs. 11.3 One 10.1 to 24.0 lbs. 28.3 One 24.1 to 60.0 lbs. 68 One 60.1 to 121.0 lbs. 136 One Over 121.0 lbs. Administer the appropriate combination of chewables

Route of Administration: Oral

In Vitro Use Guide

A dosage and time titration effect was clearly identified for fleas ingesting afoxolaner with mean efficacies of >95% recorded for fleas fed blood containing the compound at concentrations of 0.16, 0.08 and 0.02 μg/ml at the 24, 48 and 72 h observation points, respectively. There was only 1%, 2.3% and 2.3% mean mortality in the vehicle-treated control at the 24, 48 and 72 h observation points, respectively. Therefore, afoxolaner was judged to be highly active against fleas following ingestion in blood.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 07:27:55 GMT 2023` Edited by `admin` on `Sat Dec 16 07:27:55 GMT 2023`
Record UNII	02L07H6D0U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AFOXOLANER

Official Name

English

AFOXOLANER [USAN]

Common Name

English

AFOXOLANER [GREEN BOOK]

Common Name

English

AFOXOLANER CONPONENT OF NEXGARD SPECTRA

Common Name

English

4-(5-(3-CHLORO-5-(TRIFLUOROMETHYL)PHENYL)-5-(TRIFLUOROMETHYL)-4,5-DIHYDROISOXAZOL-3-YL(-N- (2-OXO-2-((2,2,2-TRIFLUOROETHYL)AMINO)ETHYL(NAPHTHALENE-1-CARBOXAMIDE

Common Name

English

NEXGARD

Brand Name

English

1-NAPHTHALENECARBOXAMIDE, 4-(5-(3-CHLORO-5-(TRIFLUOROMETHYL)PHENYL)-4,5-DIHYDRO-5- (TRIFLUOROMETHYL)-3-ISOXAZOLYL)-N-(2-OXO-2-((2,2,2-TRIFLUOROETHYL)AMINO)ETHYL)-

Common Name

English

NEXGARD SPECTRA CONPONENT AFOXOLANER

Brand Name

English

AH252723

Code

English

AFOXOLANER [EMA EPAR VETERINARY]

Common Name

English

A1443

Code

English

AFOXOLANER [MI]

Common Name

English

afoxolaner [INN]

Common Name

English

Classification Tree Code System Code

EMA VETERINARY ASSESSMENT REPORTS

NEXGARD SPECTRA [AUTHORIZED]