SONEPIPRAZOLE MESYLATE

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15023570 | https://www.ncbi.nlm.nih.gov/pubmed/8968364
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D4 receptor 71 Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11170639 \| https://www.ncbi.nlm.nih.gov/pubmed/15023570	Antagonist 2778		10.1 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15023570 http://adisinsight.springer.com/drugs/800007223	Primary		Phase II 1132	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=363677848	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=363677848	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=363677848	yes [IC50 23.9185 uM]

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00AD21	https://www.1pchem.com/search?query=1P00AD21
Alfa Chemistry	10155	http://www.alfa-chemistry.com/search.aspx?q=10155
Alfa Chemistry	AFI170858330	http://www.alfa-chemistry.com/search.aspx?q=AFI170858330
ApexBio Technology	B7607	https://www.apexbt.com/catalogsearch/result/?q=B7607
Axon MedChem	2115	https://www.axonmedchem.com/product/2115
BOC Sciences	170858-33-0	http://www.bocsci.com/description.asp?cas=170858-33-0
Cayman Chemical	11983	http://www.caymanchem.com/app/template/Product.vm/catalog/11983
MolPort	MolPort-023-277-088	https://www.molport.com/shop/molecule-link/MolPort-023-277-088
MolPort	MolPort-042-665-815	https://www.molport.com/shop/molecule-link/MolPort-042-665-815
MuseChem	M034048	https://www.musechem.com/product/M034048.html
MuseChem	R053742	https://www.musechem.com/product/R053742.html
Ryan Scientific	101-94092	https://ryansci.com/products?q=101-94092&list_q=&search_type=exact
Tocris	4185	https://www.tocris.com/search.php?Type=QuickSearch&Value=4185
Toronto Research Chemicals	S676800	https://www.trc-canada.com/product-detail/?CatNum=S676800
eMolecules	275109376	https://orderbb.emolecules.com/search/#?query=275109376
eMolecules	36500266	https://orderbb.emolecules.com/search/#?query=36500266
eMolecules	49435276	https://orderbb.emolecules.com/search/#?query=49435276

PubMed

Title	Date	PubMed
Substituted 4-aminopiperidines having high in vitro affinity and selectivity for the cloned human dopamine D4 receptor.	1997 Mar 19	9098699
Certain 1,4-disubstituted aromatic piperidines and piperazines with extreme selectivity for the dopamine D4 receptor interact with a common receptor microdomain.	2004 Dec	15448188
Effectiveness of the selective D4 antagonist sonepiprazole in schizophrenia: a placebo-controlled trial.	2004 Mar 1	15023570
WAY 100635 produces discriminative stimulus effects in rats mediated by dopamine D(4) receptor activation.	2009 Feb	19179855

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 Created by `admin` on `Fri Dec 15 15:56:42 GMT 2023` Edited by `admin` on `Fri Dec 15 15:56:42 GMT 2023`
Record UNII	980MD32QLW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SONEPIPRAZOLE MESYLATE

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