SPIPERONE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H26FN3O2
Molecular Weight	395.4707
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1ccc(cc1)N2CN=C(C32CCN(CCCC(=O)c4ccc(cc4)F)CC3)O

InChI

InChIKey=DKGZKTPJOSAWFA-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C23H26FN3O2
Molecular Weight	395.4707
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.sciencedirect.com/science/article/pii/B9780080552323626558
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18786164 | https://www.ncbi.nlm.nih.gov/pubmed/10202608 | https://www.ncbi.nlm.nih.gov/pubmed/8866760

Spiperone (Spiroperidol; brand name: Spiropitan (JP)) is a typical antipsychotic and research chemical belonging to the butyrophenone chemical class. Spiperone is selective D2 dopamine receptor antagonist; α1B-adrenoceptor antagonist; mixed 5-HT2A/5-HT1 serotonin receptor antagonist. 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. Spiperone is widely used as a pharmacological tool for studying neurotransmitter receptors.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 283 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26227779	Antagonist 2575	1.08 nM [Ki]
Dopamine D4 receptor 66 Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23403082	Antagonist 2575	0.2 nM [Ki]
Dopamine D3 receptor 85 Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26227779	Antagonist 2575	0.48 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 276 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10202608	Diagnostic		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antagonistic effect of cyproheptadine on neuroleptic-induced catalepsy.	1975 Jan-Feb	1168927
Patterns of cyclic AMP formation by coexpressed D1 and D2L dopamine receptors in HEK 293 cells.	2001	11918350
Alteration of dopamine transport in the striatum and nucleus accumbens of ovariectomized and estrogen-primed rats following N-(p-isothiocyanatophenethyl) spiperone (NIPS) treatment.	2001 Apr	11403989
(-)S amisulpride binds with high affinity to cloned dopamine D(3) and D(2) receptors.	2001 Dec 7	11740949
Direct correlation between positron emission tomographic images of two reporter genes delivered by two distinct adenoviral vectors.	2001 Jul	11526454
Pharmacological characterization of the D1- and D2-like dopamine receptors from the brain of the leopard frog, Rana pipiens.	2001 Jun	11713387
Affinity of serotonin receptor antagonists and agonists to recombinant and native alpha1-adrenoceptor subtypes.	2001 Jun	11459121
Stimulation of sodium-dependent inorganic phosphate transport by activation of Gi/o-protein-coupled receptors by epinephrine in MC3T3-E1 osteoblast-like cells.	2001 Jun	11425646
The cloned human 5-HT7 receptor splice variants: a comparative characterization of their pharmacology, function and distribution.	2001 Jun	11414657
Pharmacological evaluation of (+)-2- [123I]A-69024: a radioligand for in vivo studies of dopamine D1 receptors.	2001 Jun 29	11476188
Dopamine depletion with 6-OHDA enhances dopamine D1-receptor modulation of potassium currents in retinal bipolar cells.	2001 Mar-Apr	11417806
Effects of endogenous neurotransmitters on the in vivo binding of dopamine and 5-HT radiotracers in mice.	2001 Nov	11682251
Modulation of [3H]quinpirole binding at striatal D2 dopamine receptors by a monoamine oxidaseA-like site: evidence from radioligand binding studies and D2 receptor- and MAO(A)-deficient mice.	2001 Nov 30	11787947
Noninvasive, quantitative imaging in living animals of a mutant dopamine D2 receptor reporter gene in which ligand binding is uncoupled from signal transduction.	2001 Oct	11593362
Modulation of dopamine uptake in rat nucleus accumbens: effect of specific dopamine receptor antagonists and sigma ligands.	2001 Oct 26	11602337
Dopamine inhibits vasopressin action in the rat inner medullary collecting duct via alpha(2)-adrenoceptors.	2001 Sep	11504796
Dosing time-dependent tolerance of catalepsy by repetitive administration of haloperidol in mice.	2001 Sep	11504791
Benzamide bioisosteres incorporating dihydroheteroazole substructures: EPC synthesis and SAR leading to a selective dopamine D4 receptor partial agonist (FAUC 179).	2001 Sep 17	11549463
New 1-aryl-4-(biarylmethylene)piperazines as potential atypical antipsychotics sharing dopamine D(2)-receptor and serotonin 5-HT(1A)-receptor affinities.	2001 Sep 3	11527728
Determination of dopamine D(4) receptor density in rat striatum using PB12 as a probe.	2001 Sep 7	11553357
Decreased [(3)H]spiperone binding in the anterior cingulate cortex of schizophrenia patients: an autoradiographic study.	2002	11927153
Timing is everything: the effects of putative dopamine antagonists on metamorphosis vary with larval age and experimental duration in the prosobranch gastropod Crepidula fornicata.	2002 Apr	11971809
Positron emission tomography and ex vivo and in vitro autoradiography studies on dopamine D2-like receptor degeneration in the quinolinic acid-lesioned rat striatum: comparison of [11C]raclopride, [11C]nemonapride and [11C]N-methylspiperone.	2002 Apr	11929700
(+)-[76Br]A-69024: a non-benzazepine radioligand for studies of dopamine D1 receptors using PET.	2002 Apr	11929698
Neuropharmacological profile of a novel potential atypical antipsychotic drug Y-931 (8-fluoro-12-(4-methylpiperazin-1-yl)- 6H-[1]benzothieno[2,3-b][1,5] benzodiazepine maleate).	2002 Apr	11927170
Hypothalamic paraventricular 5-hydroxytryptamine: receptor-specific inhibition of NPY-stimulated eating and energy metabolism.	2002 Apr	11888562
Physiologically identified 5-HT2-like receptors at the crayfish neuromuscular junction.	2002 Apr 5	11911865
Metachlorophenylpiperazine (m-CPP) induced intracavernous pressure responses in anaesthetized rats.	2002 Aug	12152119
Functional cooperation between neurosteroids and D2 dopamine antagonists on KCl-evoked [3H]noradrenaline release: modulation by calcium channel blockers.	2002 Dec	12472876
Characterization of 5-HT receptor subtypes mediating contraction in human umbilical vein. 1. Evidence of involvement of 5-HT2A receptors using functional and radioligand binding assays.	2002 Dec	12444501
Inhibition of protein tyrosine/mitogen-activated protein kinase phosphatase activity is associated with D2 dopamine receptor supersensitivity in a rat model of Parkinson's disease.	2002 Dec	12435803
Novel (bisarylmethoxy)butylpiperidine analogues as neurotransmitter transporter inhibitors with activity at dopamine receptor sites.	2002 Dec	12413863
In vitro evidence that 5-hydroxytryptamine increases efflux of glial glutamate via 5-HT(2A) receptor activation.	2002 Feb 1	11813245
A novel series of hybrid compounds derived by combining 2-aminotetralin and piperazine fragments: binding activity at D2 and D3 receptors.	2002 Feb 25	11844685
Nad-299 antagonises 5-HT-stimulated and spiperone-inhibited [35S]GTPgammaS binding in cloned 5-HT1A receptors.	2002 Feb-Nov	12503636
Implementation and evaluation of a 3D one-step late reconstruction algorithm for 3D positron emission tomography brain studies using median root prior.	2002 Jan	11807602
Effects of some steroids and other compounds on ovarian growth of the red swamp crayfish, Procambarus clarkii, during early vitellogenesis.	2002 Jan 1	11754024
Functional screening of G protein-coupled receptors by measuring intracellular calcium with a fluorescence microplate reader.	2002 Jun	12097186
The human 5-HT7 serotonin receptor splice variants: constitutive activity and inverse agonist effects.	2002 Mar	11906971
The atypical 5-HT2 receptor mediating tachycardia in pithed rats: pharmacological correlation with the 5-HT2A receptor subtype.	2002 Mar	11906967
Hemiparkinsonism associated with a mesencephalic tumor.	2002 May 15	11997073
Apomorphine induces trophic factors that support fetal rat mesencephalic dopaminergic neurons in cultures.	2002 Nov	12453049
Spreading depression: imaging and blockade in the rat neocortical brain slice.	2002 Nov	12424306
Changes in electrophysiological properties of lamprey spinal motoneurons during fictive swimming.	2002 Nov	12424286
In vivo serotonin 5HT(2A) receptor binding and personality traits in healthy subjects: a positron emission tomography study.	2002 Nov	12414286
Synthesis and structure-activity relationship of the isoindolinyl benzisoxazolpiperidines as potent, selective, and orally active human dopamine D4 receptor antagonists.	2002 Oct 4	12362366
Antibody capture assay reveals bell-shaped concentration-response isotherms for h5-HT(1A) receptor-mediated Galpha(i3) activation: conformational selection by high-efficacy agonists, and relationship to trafficking of receptor signaling.	2002 Sep	12181435
Corticotropin-releasing factor as well as opioid and dopamine are involved in tail-pinch-induced food intake of rats.	2003	12559107
In vivo evidence for dopamine-mediated internalization of D2-receptors after amphetamine: differential findings with [3H]raclopride versus [3H]spiperone.	2003 Feb	12527818
Characterization of the 5-hydroxytryptamine receptors mediating contraction in the pig isolated intravesical ureter.	2003 Jan	12522083

Patents

Sample Use Guides

In Vivo Use Guide

Rat: i.v. injection 12 mkCi (180 ng).

Route of Administration: Intravenous

In Vitro Use Guide

Aliquots of lymphocyte suspension containing 1 x 106- 2 x 106 cells in a final volume of 1.0 mL were incubated in duplicate for 1 hour at 37°C with varying concentrations of 3H-spiperone (0.1—4 nM) in the presence or absence of 10 5 M haloperidol. Cell viability, checked in a number of samples incubated in the absence of 3H-spiperone by their ability to exclude trypan blue, always exceeded 98%. After incubation, the samples were filtered (type GF/B) and rinsed six times with 4 ml cooled buffer B. The filters were dried and transferred to mini-vials with 5 mL hydro-luma scintillation fluid; radioactivity was counted in a liquid scintillation counter.

Substance Class	Chemical Created by `admin` on `Sat Jun 26 14:14:15 UTC 2021` Edited by `admin` on `Sat Jun 26 14:14:15 UTC 2021`
Record UNII	4X6E73CJ0Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SPIPERONE

Official Name

English

SPIPERONE [WHO-DD]

Common Name

English

SPIPERONE [INN]

Common Name

English

NSC-170983

Code

English

R-5147

Code

English

SPIPERONE [MART.]

Common Name

English

SPIROPITAN

Brand Name

English

SPIPERONE [MI]

Common Name

English

SPIPERONE [USAN]

Common Name

English

SPIPERONE [JAN]

Common Name

English

R 5147

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C28197