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

Molecular Formula	C21H24FN3O2S
Molecular Weight	401.498
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/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 237 Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9935052 \| https://www.ncbi.nlm.nih.gov/pubmed/2524857	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9892300	Diagnostic		Not Provided 511	Unknown Approved Use Unknown
Depression 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10401447	Diagnostic		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effect of electroconvulsive therapy on brain 5-HT(2) receptors in major depression.	2010-06	20513859
Serotonin 2A receptors and visual hallucinations in Parkinson disease.	2010-04	20385906
Is desire for social relationships mediated by the serotonergic system in the prefrontal cortex? An [(18)F]setoperone PET study.	2010	20198536
Test-retest variability of high resolution positron emission tomography (PET) imaging of cortical serotonin (5HT2A) receptors in older, healthy adults.	2009-07-06	19580676
Cortical serotonin type-2 receptor density in parents of children with autism spectrum disorders.	2009-01	18592367
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.	2007-09	17728427
Occupancy of striatal and extrastriatal dopamine D2/D3 receptors by olanzapine and haloperidol.	2005-12	16123775
Electroconvulsive shock decreases binding to 5-HT2 receptors in nonhuman primates: an in vivo positron emission tomography study with [18F]setoperone.	2005-05-01	15860341
A positron emission tomography study of the effects of treatment with valproate on brain 5-HT2A receptors in acute mania.	2005	16225561
EMD 281014, a specific and potent 5HT2 antagonist in humans: a dose-finding PET study.	2004-09	15007535
A PET study of dopamine D2 and serotonin 5-HT2 receptor occupancy in patients with schizophrenia treated with therapeutic doses of ziprasidone.	2004-05	15121646
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.	2003-06-19	12816549
Dysfunctional attitudes and 5-HT2 receptors during depression and self-harm.	2003-01	12505806
Effects of rapid tryptophan depletion on brain 5-HT(2) receptors: a PET study.	2001-05	11331561
The effect of paroxetine on 5-HT(2A) receptors in depression: an [(18)F]setoperone PET imaging study.	2001-01	11136637
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

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:21:42 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:42 GMT 2025`
Record UNII	BQ67CS3Q3E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

R 52,245

Preferred Name

English

SETOPERONE

Official Name

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