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Spiperone






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From Wikipedia, the free encyclopedia
  

Spiperone
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • Rx-only (JP)
Pharmacokinetic data
MetabolismHepatic
ExcretionRenal
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 InfoCard100.010.931 Edit this at Wikidata
Chemical and physical data
FormulaC23H26FN3O2
Molar mass395.478 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) checkY

  • Key:DKGZKTPJOSAWFA-UHFFFAOYSA-N checkY

  (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 (December 2008). "The antipsychotic spiperone attenuates inflammatory response in cultured microglia via the reduction of proinflammatory cytokine expression and nitric oxide production". Journal of Neurochemistry. 107 (5): 1225–1235. doi:10.1111/j.1471-4159.2008.05675.x. PMID 18786164.
  • ^ "Mirtazapine". Martindale: The Complete Drug Reference. The Royal Pharmaceutical Society of Great Britain. 12 September 2011. Retrieved 4 November 2013.
  • ^ Liang L, MacDonald K, Schwiebert EM, Zeitlin PL, Guggino WB (January 2009). "Spiperone, identified through compound screening, activates calcium-dependent chloride secretion in the airway". American Journal of Physiology. Cell Physiology. 296 (1): C131–C141. doi:10.1152/ajpcell.00346.2008. PMC 4116347. PMID 18987251.
  • ^ 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.
  • ^ Andrée B, Nyberg S, Ito H, Ginovart N, Brunner F, Jaquet F, et al. (August 1998). "Positron emission tomographic analysis of dose-dependent MDL 100,907 binding to 5-hydroxytryptamine-2A receptors in the human brain". Journal of Clinical Psychopharmacology. 18 (4): 317–323. doi:10.1097/00004714-199808000-00012. PMID 9690698.

    • Retrieved from "https://en.wikipedia.org/w/index.php?title=Spiperone&oldid=1189981726"
    Categories: 
    ●Drugs not assigned an ATC code
     ●5-HT2A antagonists
     ●Alpha-1 blockers
     ●Butyrophenone antipsychotics
     ●D2 antagonists
     ●Fluoroarenes
     ●Imidazolidinones
     ●Spiro compounds
     ●Typical antipsychotics
     Hidden categories: 
    ●Articles with short description
     ●Short description matches Wikidata
     ●Drugs with non-standard legal status
     ●ECHA InfoCard ID from Wikidata
     ●Chemical pages without DrugBank identifier
      


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