U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H18Cl2F4N2O5S
Molecular Weight 581.364
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SAROLANER

SMILES

CS(=O)(=O)CC(=O)N1CC2(C1)OCC3=C2C=CC(=C3)C4=NO[C@@](C4)(C5=CC(Cl)=C(F)C(Cl)=C5)C(F)(F)F

InChI

InChIKey=FLEFKKUZMDEUIP-QFIPXVFZSA-N
InChI=1S/C23H18Cl2F4N2O5S/c1-37(33,34)9-19(32)31-10-21(11-31)15-3-2-12(4-13(15)8-35-21)18-7-22(36-30-18,23(27,28)29)14-5-16(24)20(26)17(25)6-14/h2-6H,7-11H2,1H3/t22-/m0/s1

HIDE SMILES / InChI

Molecular Formula C23H18Cl2F4N2O5S
Molecular Weight 581.364
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Sarolaner is a member of the isoxazoline class of parasiticides. It is sold under the brand name Simparica, indicated for the treatment of tick infestations (Dermacentor reticulatus, Ixodes hexagonus, Ixodes ricinus and Rhipicephalus sanguineus), as well as of flea infestations (Ctenocephalides felis and Ctenocephalides canis) in dogs. The primary target of action of sarolaner in insects and acarines is functional blockade of ligand-gated chloride channels (GABA-receptors and glutamate-receptors). Sarolaner blocks GABA- and glutamate-gated chloride channels in the central nervous system of insects and acarines. Disruption of these receptors by sarolaner prevents the uptake of chloride ions by GABA and glutamate gated ion channels, thus resulting in increased nerve stimulation and death of the target parasite. Sarolaner exhibits higher functional potency to block insect/acarine receptors compared to mammalian receptors.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Simparica

Approved Use

For the treatment of tick infestations (Dermacentor reticulatus, Ixodes hexagonus, Ixodes ricinus and Rhipicephalus sanguineus). The veterinary medicinal product has immediate and persistent tick killing activity for at least 5 weeks. For the treatment of flea infestations (Ctenocephalides felis and Ctenocephalides canis). The veterinary medicinal product has immediate and persistent flea killing activity against new infestations for at least 5 weeks. The veterinary medicinal product can be used as part of a treatment strategy for the control of Flea Allergy Dermatitis (FAD).

Launch Date

2016
Curative
Simparica

Approved Use

For the treatment of tick infestations (Dermacentor reticulatus, Ixodes hexagonus, Ixodes ricinus and Rhipicephalus sanguineus). The veterinary medicinal product has immediate and persistent tick killing activity for at least 5 weeks. For the treatment of flea infestations (Ctenocephalides felis and Ctenocephalides canis). The veterinary medicinal product has immediate and persistent flea killing activity against new infestations for at least 5 weeks. The veterinary medicinal product can be used as part of a treatment strategy for the control of Flea Allergy Dermatitis (FAD).

Launch Date

2016
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

For oral use. Tablets can be administered with or without food. Sarolaner should be administered at a dose of 2–4 mg/kg bodyweight
Route of Administration: Oral
Sarolaner (PF-06450567) was identified as the most potent of the isoxazolines tested in the in vitro screening system with a LC80 of 0.3 ug/mL for fleas and LC 100 of 0.003 ug/mL for O. turicata soft ticks.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:08:22 GMT 2023
Edited
by admin
on Sat Dec 16 10:08:22 GMT 2023
Record UNII
DM113FTW7F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SAROLANER
INN   USAN  
USAN   INN  
Official Name English
SAROLANER COMPONENT OF STRONGHOLD PLUS
Brand Name English
SAROLANER [MI]
Common Name English
STRONGHOLD PLUS COMPONENT SAROLANER
Brand Name English
SIMPARICA
Brand Name English
1-(5'-((5S)-5-(3,5-DICHLORO-4-FLUOROPHENYL)-5-(TRIFLUOROMETHYL)-4,5-DIHYDROISOXAZOL-3-YL)-3'-H-SPIRO(AZETIDINE-3,1'-(2)BENZOFURAN)-1-YL)-2-(METHYLSULFONYL)ETHANONE
Systematic Name English
SAROLANER [GREEN BOOK]
Common Name English
SAROLANER [EMA EPAR VETERINARY]
Common Name English
PF-6450567
Code English
SAROLANER [USAN]
Common Name English
ETHANONE, 1-(5'-((5S)-5-(3,5-DICHLORO-4-FLUOROPHENYL)-4,5-DIHYDRO-5-(TRIFLUOROMETHYL)-3-ISOXAZOLYL)SPIRO(AZETIDINE-3,1'(3'H)-ISOBENZOFURAN)-1-YL)-2-(METHYLSULFONYL)-
Systematic Name English
sarolaner [INN]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 520.2086
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS SIMPARICA [AUTHORIZED ]
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
NCI_THESAURUS C276
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS STRONGHOLD PLUS [ AUTHORIZED ]
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL3137302
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
PRIMARY
SMS_ID
300000023745
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
PRIMARY
USAN
AB-99
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
PRIMARY
PUBCHEM
73169092
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
PRIMARY
NCI_THESAURUS
C152304
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
PRIMARY
CAS
1398609-39-6
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
PRIMARY
MERCK INDEX
m11907
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
PRIMARY
ALANWOOD
sarolaner
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
PRIMARY
RXCUI
1740360
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
PRIMARY
WIKIPEDIA
Sarolaner
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID101336934
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
PRIMARY
FDA UNII
DM113FTW7F
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
PRIMARY
DAILYMED
DM113FTW7F
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
PRIMARY
INN
9923
Created by admin on Sat Dec 16 10:08:22 GMT 2023 , Edited by admin on Sat Dec 16 10:08:22 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY