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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 of AFOXOLANER

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

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

2020
742
Targets

Targets

Primary TargetPharmacologyConditionPotency
insect and acarine GABA-gated chloride channels
1
Target ID: insect and acarine GABA-gated chloride channels
Blocker
537
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
NEXGARD

Approved Use

Unknown
Curative
Approved
8429
NEXGARD

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Afoxolaner against fleas: immediate efficacy and resultant mortality after short exposure on dogs.
2014
Discovery and mode of action of afoxolaner, a new isoxazoline parasiticide for dogs.
2014 Apr 2
Evaluation of the efficacy of afoxolaner against Haemaphysalis longicornis on dogs.
2014 Apr 2
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
Patents

Patents

20100249424
1
20100254959
1
20110009638
1
20110257011
1
20110263603
1

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 UTC 2023
Edited
by admin
on Sat Dec 16 07:27:55 UTC 2023
Record UNII
02L07H6D0U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AFOXOLANER
INN   USAN  
INN   USAN  
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]
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
CFR 21 CFR 520.43
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
WHO-VATC QP53BX04
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
EMA VETERINARY ASSESSMENT REPORTS NEXGARD [AUTHORIZED]
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C171791
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
PRIMARY
CAS
1093861-60-9
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
PRIMARY
USAN
ZZ-56
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
PRIMARY
MERCK INDEX
m11748
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
PRIMARY
ALANWOOD
afoxolaner
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
PRIMARY
SMS_ID
300000023671
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
PRIMARY
EPA CompTox
DTXSID50148921
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
PRIMARY
WIKIPEDIA
Afoxolaner
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
PRIMARY
ChEMBL
CHEMBL2219412
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
PRIMARY
FDA UNII
02L07H6D0U
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
PRIMARY
INN
9697
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
PRIMARY
PUBCHEM
25154249
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
PRIMARY
DAILYMED
02L07H6D0U
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
PRIMARY
RXCUI
1442093
Created by admin on Sat Dec 16 07:27:55 UTC 2023 , Edited by admin on Sat Dec 16 07:27:55 UTC 2023
PRIMARY RxNorm
Related Record Type Details
Structure of AFOXOLANER, (R)-
ENANTIOMER -> RACEMATE
Structure of ESAFOXOLANER
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of AFOXOLANER
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