Spiperone

Last updated
Spiperone
Spiperone.svg
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • Rx-only ( JP )
Pharmacokinetic data
Metabolism Hepatic
Excretion Renal
Identifiers
  • 8-[4-(4-fluorophenyl)-4-oxobutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.010.931 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C23H26FN3O2
Molar mass 395.478 g·mol−1
3D model (JSmol)
  • c1ccc(cc1)N2CNC(=O)C23CCN(CC3)CCCC(=O)c4ccc(cc4)F
  • InChI=1S/C23H26FN3O2/c24-19-10-8-18(9-11-19)21(28)7-4-14-26-15-12-23(13-16-26)22(29)25-17-27(23)20-5-2-1-3-6-20/h1-3,5-6,8-11H,4,7,12-17H2,(H,25,29) Yes check.svgY
  • Key:DKGZKTPJOSAWFA-UHFFFAOYSA-N Yes check.svgY
   (verify)

Spiperone (Spiroperidol; brand name: Spiropitan(JP)) is a typical antipsychotic and research chemical belonging to the butyrophenone chemical class. [1] It is licensed for clinical use in Japan as a treatment for schizophrenia. [2] Additionally, spiperone was identified by compound screening to be an activator of Ca2+ activated Cl channels (CaCCs), thus a potential target for therapy of cystic fibrosis. [3]

ReceptorKi (nM) [4] Notes
5-HT1A 17.3
5-HT1B 995
5-HT1D 2397
5-HT1E 5051
5-HT1F 3.98
5-HT2A 1.17
5-HT2B 1114.2
5-HT2C 922.9
5-HT3 >10000No data available from
cloned human receptors.
Data comes from rat cortex
receptors and other sources.
5-HT5A 2512Cloned mouse receptor.
5-HT6 1590Cloned rat receptor.
5-HT7 109.8
α1A 20.4
α1B 3.09
α1D 8.32
D1 398.5
D2 0.16
D3 0.34
D4 1.39
D5 4500
H1 272
σ 353

N-Methylspiperone (NMSP) is a derivate of spiperone that is used to study the dopamine and serotonin neurotransmitter system. Labeled with the radioisotope carbon-11, it can be used for positron emission tomography. [5]

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References

  1. Zheng LT, Hwang J, Ock J, Lee MG, Lee WH, Suk K (September 2008). "The antipsychotic spiperone attenuates inflammatory response in cultured microglia via the reduction of proinflammatory cytokine expression and nitric oxide production". J. Neurochem. 107 (5): 1225–35. doi: 10.1111/j.1471-4159.2008.05675.x . PMID   18786164.
  2. Mirtazapine. Martindale: The Complete Drug Reference. The Royal Pharmaceutical Society of Great Britain. 12 September 2011. Retrieved 4 November 2013.
  3. Liang L, Macdonald KD, Schwiebert EM, Zeitlin PL, Guggino WB (October 2008). "Spiperone, Identified through Compound Screening, Activates Calcium Dependent Chloride Secretion in the Airway". Am J Physiol Cell Physiol. 296 (1): C131–41. doi:10.1152/ajpcell.00346.2008. PMC   4116347 . PMID   18987251.
  4. Roth, BL; Driscol, J (12 January 2011). "PDSP Ki Database". Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Archived from the original on 8 November 2013. Retrieved 4 November 2013.
  5. Bengt Andree; et al. (August 1998). "Positron Emission Tomographic Analysis of Dose-dependent MDL-100,907 Binding to 5-Hydroxtryptamine-2A Receptors in the Human Brain". Journal of Clinical Psychopharmacology . 18 (4): 313–323.