Chemistry:Spiperone

Spiperone
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	Rx-only (Japan );
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 ;
PubChem CID	5265;
IUPHAR/BPS	99;
ChemSpider	5075 ;
UNII	4X6E73CJ0Q;
KEGG	D01051 ;
ChEBI	CHEBI:9233 ;
ChEMBL	ChEMBL267930 ;
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) ; Key:DKGZKTPJOSAWFA-UHFFFAOYSA-N ;
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Short description: Chemical compound

Spiperone (Spiroperidol; brand name: Spiropitan (Japan )) 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	K_i (nM)^[4]	Notes
5-HT_1A	17.3
5-HT_1B	995
5-HT_1D	2397
5-HT_1E	5051
5-HT_1F	3.98
5-HT_2A	1.17
5-HT_2B	1114.2
5-HT_2C	922.9
5-HT₃	>10000	No data available from cloned human receptors. Data comes from rat cortex receptors and other sources.
5-HT_5A	2512	Cloned mouse receptor.
5-HT₆	1590	Cloned rat receptor.
5-HT₇	109.8
α_1A	20.4
α_1B	3.09
α_1D	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.^[5]

References

↑ "The antipsychotic spiperone attenuates inflammatory response in cultured microglia via the reduction of proinflammatory cytokine expression and nitric oxide production". Journal of Neurochemistry 107 (5): 1225–1235. December 2008. doi:10.1111/j.1471-4159.2008.05675.x. PMID 18786164.
↑ "Mirtazapine". Martindale: The Complete Drug Reference. The Royal Pharmaceutical Society of Great Britain. 12 September 2011. http://www.medicinescomplete.com/mc/martindale/current/11022-r.htm. Retrieved 4 November 2013.
↑ "Spiperone, identified through compound screening, activates calcium-dependent chloride secretion in the airway". American Journal of Physiology. Cell Physiology 296 (1): C131–C141. January 2009. doi:10.1152/ajpcell.00346.2008. PMID 18987251.
↑ "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. 12 January 2011. http://pdsp.med.unc.edu/pdsp.php.
↑ "Positron emission tomographic analysis of dose-dependent MDL 100,907 binding to 5-hydroxytryptamine-2A receptors in the human brain". Journal of Clinical Psychopharmacology 18 (4): 317–323. August 1998. doi:10.1097/00004714-199808000-00012. PMID 9690698.

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Original source: https://en.wikipedia.org/wiki/Spiperone. Read more

[pmid18786164-1] "The antipsychotic spiperone attenuates inflammatory response in cultured microglia via the reduction of proinflammatory cytokine expression and nitric oxide production". Journal of Neurochemistry 107 (5): 1225–1235. December 2008. doi:10.1111/j.1471-4159.2008.05675.x. PMID 18786164.

[MD-2] "Mirtazapine". Martindale: The Complete Drug Reference. The Royal Pharmaceutical Society of Great Britain. 12 September 2011. http://www.medicinescomplete.com/mc/martindale/current/11022-r.htm. Retrieved 4 November 2013.

[pmid18987251-3] "Spiperone, identified through compound screening, activates calcium-dependent chloride secretion in the airway". American Journal of Physiology. Cell Physiology 296 (1): C131–C141. January 2009. doi:10.1152/ajpcell.00346.2008. PMID 18987251.

[4] "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. 12 January 2011. http://pdsp.med.unc.edu/pdsp.php.

[5] "Positron emission tomographic analysis of dose-dependent MDL 100,907 binding to 5-hydroxytryptamine-2A receptors in the human brain". Journal of Clinical Psychopharmacology 18 (4): 317–323. August 1998. doi:10.1097/00004714-199808000-00012. PMID 9690698.

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v t e Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Droperidol Haloperidol^# Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine Piperacetazine Pipotiazine Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Flupentixol Tiotixene (thiothixene) Zuclopenthixol
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Others: Molindone
Atypical	Benzisoxazole/benzisothiazoles: Iloperidone Lurasidone Paliperidone Paliperidone palmitate Perospirone Risperidone^# Ziprasidone Butyrophenones: Lumateperone^† Phenylpiperazines/quinolinones: Aripiprazole Aripiprazole lauroxil Brilaroxazine^† Brexpiprazole Cariprazine Tricyclics: Asenapine Clozapine^# Olanzapine Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Azacyclonol Cannabidiol Oxypertine Reserpine Tetrabenazine
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

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Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	none
Legal status
Legal status	Rx-only (Japan )
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
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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