spiperone

{{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

| tradename =

| Drugs.com = {{drugs.com|international|spiperone}}

| pregnancy_AU =

| pregnancy_US =

| legal_AU =

| legal_CA =

| legal_US =

| legal_status = Rx-only (JP)

| routes_of_administration = Oral

| bioavailability =

| metabolism = Hepatic

| elimination_half-life =

| excretion = Renal

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 749-02-0

| ATC_prefix = none

| ATC_suffix =

| ATC_supplemental =

| 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

| 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 (Spiroperidol; brand name: Spiropitan (JP)) is a typical antipsychotic and research chemical belonging to the butyrophenone chemical class.{{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 }} It is licensed for clinical use in Japan as a treatment for schizophrenia.{{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}} 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.{{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 }}

class="wikitable"
Receptor	Ki (nM){{cite web | title = PDSP Ki 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 }}	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{{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 = }}
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

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.{{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 }}