Spiperone

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

Spiperone

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
IUPAC name 8-[4-(4-fluorophenyl)-4-oxobutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
CAS Number	749-02-0^Y
PubChem CID	5265
IUPHAR/BPS	99
ChemSpider	5075^Y
UNII	4X6E73CJ0Q
KEGG	D01051^Y
ChEBI	CHEBI:9233^Y
ChEMBL	ChEMBL267930^Y
CompTox Dashboard (EPA)	DTXSID5045205
ECHA InfoCard	100.010.931
Chemical and physical data
Formula	C23H26FN3O2
Molar mass	395.478 g·mol^−1
3D model (JSmol)	Interactive image
SMILES c1ccc(cc1)N2CNC(=O)C23CCN(CC3)CCCC(=O)c4ccc(cc4)F
InChI 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)^Y Key:DKGZKTPJOSAWFA-UHFFFAOYSA-N^Y
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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. 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 K_i 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.