Spiperone

Chemical compound From Wikipedia, the free encyclopedia

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]

ATC code
  • none
Legal status
  • Rx-only (JP)
Quick facts Clinical data, AHFS/Drugs.com ...
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)
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Pharmacology

Pharmacodynamics

More information Receptor, Ki (nM) ...
Spiperone at targets[3]
ReceptorKi (nM)Notes
5-HT1A17.3
5-HT1B995
5-HT1D2397
5-HT1E5051
5-HT1F3.98
5-HT2A1.17
5-HT2B0.8–1114.20.8 is bovine[4]
5-HT2C922.9
5-HT3>10000Rat/other
5-HT5A2512Mouse
5-HT61590Rat
5-HT7109.8
α1A20.4
α1B3.09
α1D8.32
D1398.5
D20.16
D30.34
D41.39
D54500
H1272
σ353
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Spiperone interacts with various monoamine receptors.[5][3][6]

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.[7]

Chemistry

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.[8]

See also

References

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