SETOPERONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H24FN3O2S
Molecular Weight	401.498
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(CCN2CCC(CC2)C(=O)C3=CC=C(F)C=C3)C(=O)N4CCSC4=N1

InChI

InChIKey=RBGAHDDQSRBDOG-UHFFFAOYSA-N

InChI=1S/C21H24FN3O2S/c1-14-18(20(27)25-12-13-28-21(25)23-14)8-11-24-9-6-16(7-10-24)19(26)15-2-4-17(22)5-3-15/h2-5,16H,6-13H2,1H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1573409 | https://www.ncbi.nlm.nih.gov/pubmed/9935052 | https://www.ncbi.nlm.nih.gov/pubmed/9892300

Setoperone is and antagonist of the brain serotonin 5-HT2 receptor and particular the 5-HT2A isoform. Setoperone is radiolabeled with the radioisotope fluorine-18 and is used in positron emission tomography (PET) in neuroimaging for the study neuropsychiatric disorders, such as schizophrenia and depression.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 2a (5-HT2a) receptor 231 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9935052 \| https://www.ncbi.nlm.nih.gov/pubmed/2524857	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9892300	Diagnostic		Not Provided 504	Unknown Approved Use Unknown
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10401447	Diagnostic		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of 5-HT1A agonists and 5-HT2 antagonists on haloperidol-induced dyskinesias in squirrel monkeys: no evidence for reciprocal 5-HT-dopamine interaction.	1989	2524857
The effect of paroxetine on 5-HT(2A) receptors in depression: an [(18)F]setoperone PET imaging study.	2001 Jan	11136637
Effects of rapid tryptophan depletion on brain 5-HT(2) receptors: a PET study.	2001 May	11331561
Dysfunctional attitudes and 5-HT2 receptors during depression and self-harm.	2003 Jan	12505806
Ritanserin as an adjunct to lithium and haloperidol for the treatment of medication-naive patients with acute mania: a double blind and placebo controlled trial.	2003 Jun 19	12816549
A PET study of dopamine D2 and serotonin 5-HT2 receptor occupancy in patients with schizophrenia treated with therapeutic doses of ziprasidone.	2004 May	15121646
EMD 281014, a specific and potent 5HT2 antagonist in humans: a dose-finding PET study.	2004 Sep	15007535
A positron emission tomography study of the effects of treatment with valproate on brain 5-HT2A receptors in acute mania.	2005	16225561
Occupancy of striatal and extrastriatal dopamine D2/D3 receptors by olanzapine and haloperidol.	2005 Dec	16123775
Electroconvulsive shock decreases binding to 5-HT2 receptors in nonhuman primates: an in vivo positron emission tomography study with [18F]setoperone.	2005 May 1	15860341
Differential effects of aripiprazole on D(2), 5-HT(2), and 5-HT(1A) receptor occupancy in patients with schizophrenia: a triple tracer PET study.	2007 Sep	17728427
Cortical serotonin type-2 receptor density in parents of children with autism spectrum disorders.	2009 Jan	18592367
Test-retest variability of high resolution positron emission tomography (PET) imaging of cortical serotonin (5HT2A) receptors in older, healthy adults.	2009 Jul 6	19580676
Is desire for social relationships mediated by the serotonergic system in the prefrontal cortex? An [(18)F]setoperone PET study.	2010	20198536
Serotonin 2A receptors and visual hallucinations in Parkinson disease.	2010 Apr	20385906
Effect of electroconvulsive therapy on brain 5-HT(2) receptors in major depression.	2010 Jun	20513859

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Other

In Vitro Use Guide

Unknown

Name

Type

Language

SETOPERONE

Official Name

English

R 52,245

Code

English

SETOPERONE [USAN]

Common Name

English

5H-THIAZOLO(3,2-A)PYRIMIDIN-5-ONE, 6-(2-(4-(4-FLUOROBENZOYL)-1-PIPERIDINYL)ETHYL)-2,3-DIHYDRO-7-METHYL-

Systematic Name

English

Setoperone [WHO-DD]

Common Name

English

R-52245

Code

English

6-(2-(4-(P-FLUOROBENZOYL)PIPERIDINO)ETHYL)-2,3-DIHYDRO-7-METHYL-5H-THIAZOLO(3,2-.ALPHA.)PYRIMIDIN-5-ONE

Systematic Name

English

setoperone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197