{{Short description|Chemical compound}} {{Drugbox | verifiedrevid = 464406203 | IUPAC_name = 8-[4-(4-fluorophenyl)-4-oxobutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one | image = Spiperone.svg | image_class = skin-invert-image | width = 250
<!--Clinical data--> | tradename = | Drugs.com = {{drugs.com|international|spiperone}} | pregnancy_AU = | pregnancy_US = | legal_AU = | legal_CA = | legal_US = | legal_status = Rx-only (<small>JP</small>) | routes_of_administration = Oral
<!--Pharmacokinetic data--> | bioavailability = | metabolism = Hepatic | elimination_half-life = | excretion = Renal
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 749-02-0 | ATC_prefix = none | ATC_suffix = | ATC_supplemental = <!--{{ATC|N05|}}--> | PubChem = 5265 | IUPHAR_ligand = 99 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 5075 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 4X6E73CJ0Q | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D01051 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 9233 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 267930
<!--Chemical data--> | C=23 | H=26 | F=1 | N=3 | O=2 | smiles = c1ccc(cc1)N2CNC(=O)C23CCN(CC3)CCCC(=O)c4ccc(cc4)F | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = DKGZKTPJOSAWFA-UHFFFAOYSA-N }}
'''Spiperone''', also known as '''spiroperidol''' and sold under the brand name '''Spiropitan''' (<small>(JP)</small>) is a typical antipsychotic of the butyrophenone family related to haloperidol.<ref name="pmid18786164">{{cite journal | vauthors = Zheng LT, Hwang J, Ock J, Lee MG, Lee WH, Suk K | title = The antipsychotic spiperone attenuates inflammatory response in cultured microglia via the reduction of proinflammatory cytokine expression and nitric oxide production | journal = Journal of Neurochemistry | volume = 107 | issue = 5 | pages = 1225–1235 | date = December 2008 | pmid = 18786164 | doi = 10.1111/j.1471-4159.2008.05675.x | doi-access = free }}</ref> It is approved for clinical use in Japan as a treatment for schizophrenia.<ref name = MD>{{cite book| chapter = Mirtazapine | title = Martindale: The Complete Drug Reference|publisher=The Royal Pharmaceutical Society of Great Britain|access-date=4 November 2013|date=12 September 2011| chapter-url = http://www.medicinescomplete.com/mc/martindale/current/11022-r.htm}}</ref>
==Pharmacology== ===Pharmacodynamics=== {| class="wikitable floatleft" |+ Spiperone at targets<ref name="PDSPKiDatabase">{{cite web | title = PDSP K<sub>i</sub> Database | work = Psychoactive Drug Screening Program (PDSP) | vauthors = Roth BL, Driscol J |author1-link=Bryan Roth | url = http://pdsp.med.unc.edu/pdsp.php | publisher = University of North Carolina at Chapel Hill and the United States National Institute of Mental Health | access-date = 4 November 2013 | date = 12 January 2011 | url-status = dead | archive-url = https://web.archive.org/web/20131108013656/http://pdsp.med.unc.edu/pdsp.php | archive-date = 8 November 2013 }}</ref> |- ! Receptor !! K<sub>i</sub> (nM) !! Notes |- | 5-HT<sub>1A</sub> || 17.3 || |- | 5-HT<sub>1B</sub> || 995 || |- | 5-HT<sub>1D</sub> || 2397 || |- | 5-HT<sub>1E</sub> || 5051 || |- | 5-HT<sub>1F</sub> || 3.98 || |- | 5-HT<sub>2A</sub> || 1.17 || |- | 5-HT<sub>2B</sub> || 0.8–1114.2 || 0.8 is bovine<ref name="BenderParrLivingston2023">{{cite journal | vauthors = Bender AM, Parr LC, Livingston WB, Lindsley CW, Merryman WD | title = 2B Determined: The Future of the Serotonin Receptor 2B in Drug Discovery | journal = J Med Chem | volume = 66 | issue = 16 | pages = 11027–11039 | date = August 2023 | pmid = 37584406 | pmc = 11073569 | doi = 10.1021/acs.jmedchem.3c01178 | url = }}</ref> |- | 5-HT<sub>2C</sub> || 922.9 || |- | 5-HT<sub>3</sub> || >10000 || Rat/other |- | 5-HT<sub>5A</sub> || 2512 || Mouse |- | 5-HT<sub>6</sub> || 1590 || Rat |- | 5-HT<sub>7</sub> || 109.8 || |- | α<sub>1A</sub> || 20.4 || |- | α<sub>1B</sub> || 3.09 || |- | α<sub>1D</sub> || 8.32 || |- | D<sub>1</sub> || 398.5 || |- | D<sub>2</sub> || 0.16 || |- | D<sub>3</sub> || 0.34 || |- | D<sub>4</sub> || 1.39 || |- | D<sub>5</sub> || 4500 || |- | H<sub>1</sub> || 272 || |- | σ || 353 || |}
Spiperone interacts with various monoamine receptors.<ref name="Glennon1987">{{cite journal | vauthors = Glennon RA | title = Central serotonin receptors as targets for drug research | journal = J Med Chem | volume = 30 | issue = 1 | pages = 1–12 | date = January 1987 | pmid = 3543362 | doi = 10.1021/jm00384a001 | url = | quote = Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites}}</ref><ref name="PDSPKiDatabase" /><ref name="Janssen1982">{{cite book | last=Janssen | first=P.A.J. | title=Biochemical Immunological Pharmacology | chapter=The Pharmacology of Specific, Pure and Potent Serotonin 5-HT2 or S2-Antagonists | publisher=Elsevier | date=1982 | isbn=978-0-08-028024-0 | doi=10.1016/b978-0-08-028024-0.50006-2 | url=https://linkinghub.elsevier.com/retrieve/pii/B9780080280240500062 | access-date=17 January 2026 | page=21–33}}</ref>
Additionally, spiperone was identified by compound screening to be an activator of Ca<sup>2+</sup> activated Cl<sup>−</sup> channels (CaCCs), thus a potential target for therapy of cystic fibrosis.<ref name="pmid18987251">{{cite journal | vauthors = Liang L, MacDonald K, Schwiebert EM, Zeitlin PL, Guggino WB | title = Spiperone, identified through compound screening, activates calcium-dependent chloride secretion in the airway | journal = American Journal of Physiology. Cell Physiology | volume = 296 | issue = 1 | pages = C131–C141 | date = January 2009 | pmid = 18987251 | pmc = 4116347 | doi = 10.1152/ajpcell.00346.2008 }}</ref>
==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.<ref>{{cite journal | vauthors = Andrée B, Nyberg S, Ito H, Ginovart N, Brunner F, Jaquet F, Halldin C, Farde L | display-authors = 6 | title = Positron emission tomographic analysis of dose-dependent MDL 100,907 binding to 5-hydroxytryptamine-2A receptors in the human brain | journal = Journal of Clinical Psychopharmacology | volume = 18 | issue = 4 | pages = 317–323 | date = August 1998 | pmid = 9690698 | doi = 10.1097/00004714-199808000-00012 }}</ref>
==See also== * Spirodecanone
==References== {{Reflist}}
{{Antipsychotics}} {{Navboxes | title = Pharmacodynamics | titlestyle = background:#ccccff | list1 = {{Adrenergic receptor modulators}} {{Dopamine receptor modulators}} {{Serotonin receptor modulators}} }}
Category:5-HT2A antagonists Category:Alpha-1 blockers Category:Butyrophenone antipsychotics Category:D2 antagonists Category:4-Fluorophenyl compounds Category:Imidazolidinones Category:Spiro compounds Category:Typical antipsychotics