Setoperone

Last updated

Setoperone
Setoperone.svg
Clinical data
Other namesR-52245; R52245
Drug class Serotonin 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
Formula C21H24FN3O2S
Molar mass 401.50 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 mark.svgN
  • Key:RBGAHDDQSRBDOG-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Setoperone (INN Tooltip International Nonproprietary Name; USAN Tooltip United States Adopted Name; developmental code name R-52245) is a compound that is a ligand to the 5-HT2A receptor. [1] 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 [2] or schizophrenia. [3] The drug was first described by at least 1984. [1]

Contents

Chemistry

Synthesis

Synthesis: Radiolabelled: Setoperone synthesis.svg
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.
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