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, also known as spiroperidol and sold under the brand name Spiropitan ((JP)) is a typical antipsychotic of the butyrophenone family related to haloperidol. [1] It is approved for clinical use in Japan as a treatment for schizophrenia. [2]

Contents

Pharmacology

Spiperone at targets [3]
ReceptorKi (nM)Notes
5-HT1A 17.3
5-HT1B 995
5-HT1D 2397
5-HT1E 5051
5-HT1F 3.98
5-HT2A 1.17
5-HT2B 0.8–1114.20.8 is bovine [4]
5-HT2C 922.9
5-HT3 >10000Rat/other
5-HT5A 2512Mouse
5-HT6 1590Rat
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

Spiperone interacts with various monoamine receptors. [5] [3]

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. [6]

Derivatives

N-Methylspiperone (NMSP) is a derivative 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. [7]

See also

References

  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.
  2. ↑ "Mirtazapine". Martindale: The Complete Drug Reference. The Royal Pharmaceutical Society of Great Britain. 12 September 2011. Retrieved 4 November 2013.
  3. 1 2 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.
  4. ↑ Bender AM, Parr LC, Livingston WB, Lindsley CW, Merryman WD (August 2023). "2B Determined: The Future of the Serotonin Receptor 2B in Drug Discovery". J Med Chem. 66 (16): 11027–11039. doi:10.1021/acs.jmedchem.3c01178. PMC   11073569 . PMID   37584406.
  5. ↑ Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID   3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
  6. ↑ 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.
  7. ↑ 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.
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