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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H27N3O3S.CH4O3S
Molecular Weight 497.628
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SONEPIPRAZOLE MESYLATE

SMILES

CS(O)(=O)=O.NS(=O)(=O)C1=CC=C(C=C1)N2CCN(CC[C@@H]3OCCC4=C3C=CC=C4)CC2

InChI

InChIKey=GFNAQGUENCOUHQ-BOXHHOBZSA-N
InChI=1S/C21H27N3O3S.CH4O3S/c22-28(25,26)19-7-5-18(6-8-19)24-14-12-23(13-15-24)11-9-21-20-4-2-1-3-17(20)10-16-27-21;1-5(2,3)4/h1-8,21H,9-16H2,(H2,22,25,26);1H3,(H,2,3,4)/t21-;/m0./s1

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C21H27N3O3S
Molecular Weight 401.522
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

Sonepiprazole exhibits highly specific binding to the D4 dopamine receptor with more than 100-fold selectivity for the D4 receptor over other receptors, including dopamine, serotonin, and adrenergic receptors. It is a neutral antagonist at the D4 dopamine receptor and is devoid of dopamine agonist activity. Sonepiprazole selectively induces c-fos expression in the prefrontal cortex and blocks behavioral, biochemical, and genomic effects of repeated amphetamine administration in rats. Sonepiprazole was investigated as an antipsychotic for the treatment of schizophrenia in a placebo-controlled clinical trial, but in contrast to its comparator olanzapine no benefits were found and it was not researched further for this indication.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
10.1 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
1 capsule containing sonepiprazole (1.5, 10, or 60 mg) once daily in the morning.
Route of Administration: Oral
In Vitro Use Guide
In the presence of Sonepiprazole (10 uM; 3 min exposure duration), six of nine murine neurons displayed an increased frequency of spontaneous inward currents
Substance Class Chemical
Record UNII
980MD32QLW
Record Status Validated (UNII)
Record Version