Spiperone

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Spiperone
Spiperone2DACS.svg
Systematic (IUPAC) name
8-[4-(4-fluorophenyl)-4-oxo-butyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
  • Prescription only
Routes Oral
Pharmacokinetic data
Metabolism Hepatic
Excretion Renal
Identifiers
CAS number 749-02-0 YesY
ATC code None
PubChem CID 5265
IUPHAR ligand 99
ChemSpider 5075 YesY
UNII 4X6E73CJ0Q YesY
KEGG D01051 YesY
ChEBI CHEBI:9233 YesY
ChEMBL CHEMBL267930 YesY
Chemical data
Formula C23H26FN3O2 
Mol. mass 395.47 g/mol
 YesY (what is this?)  (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]

Receptor Ki (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 >10000 No data available from
cloned human receptors.
Data comes from rat cortex
receptors and other sources.
5-HT5A 2512 Cloned mouse receptor.
5-HT6 1590 Cloned 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]

References[edit]

  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. 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. Retrieved 4 November 2013. 
  5. ^ Bengt Andree and others (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.