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Spiperone

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This is an old revision of this page, as edited by Jytdog (talk | contribs) at 11:23, 21 November 2016 (primary source; need a secondary source to show that this compound is worth discussing). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

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 mass395.47 g/mol 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

  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. The Royal Pharmaceutical Society of Great Britain. 12 September 2011. Retrieved 4 November 2013. {{cite book}}: |work= ignored (help)
  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; 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.
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