Setoperone

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Setoperone
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Clinical data
Other namesR-52245; R52245
Drug classSerotonin 5-HT2A receptor antagonist
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  • 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
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Chemical and physical data
FormulaC21H24FN3O2S
Molar mass401.50 g·mol−1
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  • 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 ☒N
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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.[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]

Chemistry

Synthesis

File:Setoperone synthesis.svg
Synthesis:[4] Radiolabelled:[5]

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

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  1. ^ a b Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content."Setoperone". Drugs of the Future. 10 (1): 40. 1985.
  5. ^ Page Module:Citation/CS1/styles.css has no content.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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