Setoperone

---

title: "Setoperone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["5-ht2a-antagonists", "abandoned-drugs", "aromatic-ketones", "4-fluorophenyl-compounds", "piperidines", "thiazolopyrimidines"] topic_path: "arts/music" source: "https://en.wikipedia.org/wiki/Setoperone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::data[format=table title="Infobox drug"]

Field	Value
Verifiedfields	changed
Watchedfields	changed
verifiedrevid	449587261
image	Setoperone.svg
image_class	skin-invert-image
class	Serotonin 5-HT2A receptor antagonist
ATC_prefix	None
CAS_number_Ref
CAS_number	86487-64-1
PubChem	68604
ChemSpiderID_Ref
ChemSpiderID	61870
UNII_Ref
UNII	BQ67CS3Q3E
KEGG_Ref
KEGG	D02686
synonyms	R-52245; R52245
IUPAC_name	6-{2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl}-7-methyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
C	21
SMILES	CC1=C(C(=O)N2CCSC2=N1)CCN3CCC(CC3)C(=O)C4=CC=C(C=C4)F
StdInChI_Ref
StdInChI	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
StdInChIKey_Ref
StdInChIKey	RBGAHDDQSRBDOG-UHFFFAOYSA-N
::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 449587261 | drug_name = | image = Setoperone.svg | image_class = skin-invert-image | width = | caption =

| pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = | class = Serotonin 5-HT2A receptor antagonist | ATC_prefix = None | ATC_suffix =

| legal_status =

| bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion =

| CAS_number_Ref = | CAS_number = 86487-64-1 | CAS_supplemental = | PubChem = 68604 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 61870 | UNII_Ref = | UNII = BQ67CS3Q3E | KEGG_Ref = | KEGG = D02686 | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = R-52245; R52245

| IUPAC_name = 6-{2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl}-7-methyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one | C=21 | H=24 | F=1 | N=3 | O=2 | S=1 | SMILES = CC1=C(C(=O)N2CCSC2=N1)CCN3CCC(CC3)C(=O)C4=CC=C(C=C4)F | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = RBGAHDDQSRBDOG-UHFFFAOYSA-N

Setoperone (; ; developmental code name R-52245) is a compound that is a ligand to the 5-HT2A receptor. It can be radiolabeled with the radioisotope fluorine-18 and used as a radioligand with positron emission tomography (PET). Several research studies have used the radiolabeled setoperone in neuroimaging for the studying neuropsychiatric disorders, such as depression or schizophrenia. The drug was first described by at least 1984.

Chemistry

Synthesis

::figure[src="https://upload.wikimedia.org/wikipedia/commons/f/fd/Setoperone_synthesis.svg" caption="4443451}} (1984 to Janssen Pharmaceutica N.V.). Radiolabelled:Maziere, B.; Crouzel, C.; Venet, M.; Stulzaft, O.; Sanz, G.; Ottaviani, M.; Sejourne, C.; Pascal, O.; Bisserbe, J.C. (1988). "Synthesis, affinity and specificity of 18F-setoperone, a potential ligand for in-vivo imaging of cortical serotonin receptors". International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology. 15 (4): 463–468. doi:10.1016/0883-2897(88)90018-9."] ::

The starting material is called 6-(2-hydroxyethyl)-7-methyl-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-5-one, CID:15586462 (1). Halogenation of this with hydrobromic acid in acetic acid gives CID:15586463 (2). Sn2 alkylation with 4-(4-fluorobenzoyl)piperidine [56346-57-7] (3) under Finkelstein reaction conditions affords setoperone (4).

References

References

1. Elks, J.. (14 November 2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer.
2. [[Jeffrey H. Meyer]], Shitij Kapur, [[Sylvain Houle]], Jean DaSilva, Beata Owczarek, Gregory M. Brown, Alan A. Wilson and Sidney H. Kennedy. (July 1, 1999). "Prefrontal Cortex 5-HT2 Receptors in Depression: An [¹⁸F]Setoperone PET Imaging Study". [[American Journal of Psychiatry]].
3. Ralph Lewis, Shitij Kapur, Corey Jones, Jean DaSilva, Gregory M. Brown, Alan A. Wilson, [[Sylvain Houle]] and Robert B. Zipursky. (January 1, 1999). "Serotonin 5-HT₂ Receptors in Schizophrenia: A PET Study Using [¹⁸F]Setoperone in Neuroleptic-Naive Patients and Normal Subjects". [[American Journal of Psychiatry]].
4. [https://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_toc_pr?p_JournalID=2&p_IssueID=178 Drugs of the Future, 10, 1, 40 (1985).]
5. EP0070053 idem Ludo E. J. Kennis, Josephus C. Mertens, {{US patent. 4443451 (1984 to Janssen Pharmaceutica N.V.).
6. Maziere, B.; Crouzel, C.; Venet, M.; Stulzaft, O.; Sanz, G.; Ottaviani, M.; Sejourne, C.; Pascal, O.; Bisserbe, J.C. (1988). "Synthesis, affinity and specificity of 18F-setoperone, a potential ligand for in-vivo imaging of cortical serotonin receptors". International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology. 15 (4): 463–468. doi:10.1016/0883-2897(88)90018-9.

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