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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
136.0 nM [IC50]
136.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Simparica
Curative
Simparica

Cmax

ValueDoseCo-administeredAnalytePopulation
1100 ng/mL
20 mg/kg single, oral
SAROLANER plasma
Canis lupus

T1/2

ValueDoseCo-administeredAnalytePopulation
11.5 day
20 mg/kg single, oral
SAROLANER plasma
Canis lupus

Funbound

ValueDoseCo-administeredAnalytePopulation
0.1%
20 mg/kg single, oral
SAROLANER plasma
Canis lupus

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
DM113FTW7F
Record Status Validated (UNII)
Record Version