Spiperone

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]

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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Pharmacology

Spiperone at targets^[3]

Receptor	Ki (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	0.8–1114.2	0.8 is bovine[4]
5-HT2C	922.9
5-HT3	>10000	Rat/other
5-HT5A	2512	Mouse
5-HT6	1590	Rat
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

• Spirodecanone