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
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
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10989267
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.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Substituted 4-aminopiperidines having high in vitro affinity and selectivity for the cloned human dopamine D4 receptor. | 1997 Mar 19 |
|
| Certain 1,4-disubstituted aromatic piperidines and piperazines with extreme selectivity for the dopamine D4 receptor interact with a common receptor microdomain. | 2004 Dec |
|
| Effectiveness of the selective D4 antagonist sonepiprazole in schizophrenia: a placebo-controlled trial. | 2004 Mar 1 |
|
| WAY 100635 produces discriminative stimulus effects in rats mediated by dopamine D(4) receptor activation. | 2009 Feb |
Patents
Sample Use Guides
1 capsule containing sonepiprazole (1.5, 10, or 60 mg) once daily in the morning.
Route of Administration:
Oral
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C66883
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170858-34-1
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JJ-53
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133078
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DTXSID00168957
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CHEMBL69759
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980MD32QLW
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C84177
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ACTIVE MOIETY
SUBSTANCE RECORD
