Setoperone

Setoperone
Clinical data
Other namesR-52245; R52245
Drug classSerotonin 5-HT2A receptor antagonist
ATC code
  • None
Identifiers
  • 6-{2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl}-7-methyl-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H24FN3O2S
Molar mass401.50 g·mol−1
3D model (JSmol)
  • CC1=C(C(=O)N2CCSC2=N1)CCN3CCC(CC3)C(=O)C4=CC=C(C=C4)F
  • 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 X markN
  • Key:RBGAHDDQSRBDOG-UHFFFAOYSA-N X markN
 X markNcheckY (what is this?)  (verify)

Setoperone (INNTooltip International Nonproprietary Name; USANTooltip United States Adopted Name; 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

Synthesis: Radiolabelled:

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).

See also

References

  1. 1 2 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. ISBN 978-1-4757-2085-3. Retrieved 17 January 2026.
  2. ↑ Meyer JH, Kapur S, Houle S, DaSilva J, Owczarek B, Brown GM, et al. (July 1999). "Prefrontal cortex 5-HT2 receptors in depression: an [18F]setoperone PET imaging study". The American Journal of Psychiatry. 156 (7): 1029–1034. doi:10.1176/ajp.156.7.1029. PMID 10401447. S2CID 453720.
  3. ↑ Lewis R, Kapur S, Jones C, DaSilva J, Brown GM, Wilson AA, et al. (January 1999). "Serotonin 5-HT2 receptors in schizophrenia: a PET study using [18F]setoperone in neuroleptic-naive patients and normal subjects". The American Journal of Psychiatry. 156 (1): 72–78. doi:10.1176/ajp.156.1.72. PMID 9892300.
  4. ↑ "Setoperone". Drugs of the Future. 10 (1): 40. 1985.
  5. ↑ Maziere B, Crouzel C, Venet M, Stulzaft O, Sanz G, Ottaviani M, et al. (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): 463–8. doi:10.1016/0883-2897(88)90018-9. PMID 3255742.