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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 C21H27N3O3S
Molecular Weight 401.522
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10989267

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

Curator's Comment: The induction of c-fos mRNA in the rat medial prefrontal cortex, the blockade of amphetamine-induced behavioral sensitization and associated genomic changes, and the cognitive effects of sonepiprazole in nonhuman primates all provide evidence of central nervous system (CNS) penetration of the drug at peripherally administered doses of as low as 0.1 mg/kg.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.1 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
Substituted 4-aminopiperidines having high in vitro affinity and selectivity for the cloned human dopamine D4 receptor.
1997 Mar 19
Effectiveness of the selective D4 antagonist sonepiprazole in schizophrenia: a placebo-controlled trial.
2004 Mar 1
Patents

Patents

Sample Use Guides

1 capsule containing sonepiprazole (1.5, 10, or 60 mg) once daily in the morning.
Route of Administration: Oral
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
Created
by admin
on Fri Dec 15 15:56:42 UTC 2023
Edited
by admin
on Fri Dec 15 15:56:42 UTC 2023
Record UNII
980MD32QLW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SONEPIPRAZOLE MESYLATE
USAN  
USAN  
Official Name English
PNU-101387G
Code English
SONEPIPRAZOLE MESYLATE [USAN]
Common Name English
(S)-4-(4-(2-(3,4-DIHYDRO-1H-2-BENZOPYRAN-1-YL)ETHYL)-1-PIPERAZINYL)BENZENESULPHONAMIDE MONOMETHANESULPHONATE
Systematic Name English
SONEPIPRAZOLE MESILATE
Common Name English
(-)-P-(4-(2-((S)-1-ISOCHROMANYL)ETHYL)-1-PIPERAZINYL)BENZENESULPHONAMIDE MONOMETHANESULPHONATE
Common Name English
(S)-4-(4-(2-(3,4-DIHYDRO-1H-2-BENZOPYRAN-1-YL)ETHYL)-1-PIPERAZINYL)BENZENESULFONAMIDE MONOMETHANESULFONATE
Systematic Name English
(-)-P-(4-(2-((S)-1-ISOCHROMANYL)ETHYL)-1-PIPERAZINYL)BENZENESULFONAMIDE MONOMETHANESULFONATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66883
Created by admin on Fri Dec 15 15:56:42 UTC 2023 , Edited by admin on Fri Dec 15 15:56:42 UTC 2023
Code System Code Type Description
CAS
170858-34-1
Created by admin on Fri Dec 15 15:56:42 UTC 2023 , Edited by admin on Fri Dec 15 15:56:42 UTC 2023
PRIMARY
USAN
JJ-53
Created by admin on Fri Dec 15 15:56:42 UTC 2023 , Edited by admin on Fri Dec 15 15:56:42 UTC 2023
PRIMARY
PUBCHEM
133078
Created by admin on Fri Dec 15 15:56:42 UTC 2023 , Edited by admin on Fri Dec 15 15:56:42 UTC 2023
PRIMARY
EPA CompTox
DTXSID00168957
Created by admin on Fri Dec 15 15:56:42 UTC 2023 , Edited by admin on Fri Dec 15 15:56:42 UTC 2023
PRIMARY
ChEMBL
CHEMBL69759
Created by admin on Fri Dec 15 15:56:42 UTC 2023 , Edited by admin on Fri Dec 15 15:56:42 UTC 2023
PRIMARY
FDA UNII
980MD32QLW
Created by admin on Fri Dec 15 15:56:42 UTC 2023 , Edited by admin on Fri Dec 15 15:56:42 UTC 2023
PRIMARY
NCI_THESAURUS
C84177
Created by admin on Fri Dec 15 15:56:42 UTC 2023 , Edited by admin on Fri Dec 15 15:56:42 UTC 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY