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S7395

Sigma-Aldrich

Spiperone

solid

Synonyme(s) :

8-[3-(p-Fluorobenzoyl)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one, R 5147, Spiroperidol

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About This Item

Formule empirique (notation de Hill):
C23H26FN3O2
Numéro CAS:
749-02-0
Poids moléculaire :
395.47
Numéro CE :
212-024-0
Numéro MDL:
MFCD00055099
Code UNSPSC :
12352200
ID de substance PubChem :
24277908
Nomenclature NACRES :
NA.77

Forme

solid

Niveau de qualité

200

Couleur

light yellow

Solubilité

H2O: slightly soluble 0.2 mg/mL
0.1 M HCl: slightly soluble 0.3 mg/mL
ethanol: 1.5 mg/mL
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 2 mg/mL

Chaîne SMILES 

Fc1ccc(cc1)C(=O)CCCN2CCC3(CC2)N(CNC3=O)c4ccccc4

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)

Clé InChI

DKGZKTPJOSAWFA-UHFFFAOYSA-N

Informations sur le gène

human ... ADRA1B(147) , DRD2(1813) , DRD3(1814) , HTR1A(3350) , HTR1B(3351) , HTR1D(3352) , HTR1E(3354) , HTR1F(3355) , HTR2A(3356)
rat ... Adra1a(29412) , Adra1b(24173) , Adra1d(29413) , Adra2a(25083) , Drd1a(24316) , Drd2(24318) , Drd3(29238) , Htr1a(24473) , Htr2a(29595) , Htr2c(25187) , Htr7(65032)

Description générale

Spiperone is a butyrophenone antipsychotic agent. It induces calcium-dependent chloride secretion in the airway and functions as a potential therapeutic target for cystic fibrosis.

Application

Spiperone has been used to block the actions of 5-hydroxytryptamine (5-HT) receptor. It also has been used to study its anti tumor effects in glioblastoma (GBM) cell lines.
Spiperone was used to study the role of dopamine receptors in facilitating the male sexual behavior in quails.6

Actions biochimiques/physiologiques

Selective D2 dopamine receptor antagonist; α1B-adrenoceptor antagonist; mixed 5-HT2A/5-HT1 serotonin receptor antagonist; antipsychotic.

Reconstitution

Solutions may be stored for 1-2 days at 4 °C.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Warning

Mentions de danger

H302,H361

Classification des risques

Acute Tox. 4 Oral - Repr. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Carmen Klein Herenbrink et al.
Nature communications, 7, 10842-10842 (2016-02-26)
Biased agonism describes the ability of ligands to stabilize different conformations of a GPCR linked to distinct functional outcomes and offers the prospect of designing pathway-specific drugs that avoid on-target side effects. This mechanism is usually inferred from pharmacological data
Marion Schuller et al.
ChemMedChem, 12(19), 1585-1594 (2017-08-05)
MS Binding Assays are a label-free alternative to radioligand binding assays. They provide basically the same capabilities as the latter, but use a non-labeled reporter ligand instead of a radioligand. In contrast to radioligand binding assays, MS Binding Assays offer-owing
Spiperone enhances intracellular calcium level and inhibits the Wnt signaling pathway
Lu D and Carson DA
BioMed Central Pharmacology, 9(1), 13-13 (2009)
Michael De Santis et al.
Neuropsychiatric disease and treatment, 14, 1569-1583 (2018-06-29)
Antipsychotic drug (APD) prescription/use in children has increased significantly worldwide, despite limited insight into potential long-term effects of treatment on adult brain functioning. While initial long-term studies have uncovered alterations to behaviors following early APD treatment, further investigations into potential
D D Fraser et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 11(9), 2812-2820 (1991-09-01)
Interneurons from the CA1 lacunosum-moleculare (L-M) region were isolated by trypsin-hyaluronidase treatment and mechanical trituration of the L-M. Interneurons isolated in this manner were multipolar with several dendritic processes and could be distinguished from CA1 pyramidal neurons. The properties of
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