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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 of SPIPERONE

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.08 nM [Ki]
0.2 nM [Ki]
0.48 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antagonistic effect of cyproheptadine on neuroleptic-induced catalepsy.
1975 Jan-Feb
Patterns of cyclic AMP formation by coexpressed D1 and D2L dopamine receptors in HEK 293 cells.
2001
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
(-)S amisulpride binds with high affinity to cloned dopamine D(3) and D(2) receptors.
2001 Dec 7
Direct correlation between positron emission tomographic images of two reporter genes delivered by two distinct adenoviral vectors.
2001 Jul
Pharmacological characterization of the D1- and D2-like dopamine receptors from the brain of the leopard frog, Rana pipiens.
2001 Jun
Affinity of serotonin receptor antagonists and agonists to recombinant and native alpha1-adrenoceptor subtypes.
2001 Jun
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
The cloned human 5-HT7 receptor splice variants: a comparative characterization of their pharmacology, function and distribution.
2001 Jun
Pharmacological evaluation of (+)-2- [123I]A-69024: a radioligand for in vivo studies of dopamine D1 receptors.
2001 Jun 29
Dopamine depletion with 6-OHDA enhances dopamine D1-receptor modulation of potassium currents in retinal bipolar cells.
2001 Mar-Apr
Effects of endogenous neurotransmitters on the in vivo binding of dopamine and 5-HT radiotracers in mice.
2001 Nov
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
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
Modulation of dopamine uptake in rat nucleus accumbens: effect of specific dopamine receptor antagonists and sigma ligands.
2001 Oct 26
Dopamine inhibits vasopressin action in the rat inner medullary collecting duct via alpha(2)-adrenoceptors.
2001 Sep
Dosing time-dependent tolerance of catalepsy by repetitive administration of haloperidol in mice.
2001 Sep
Benzamide bioisosteres incorporating dihydroheteroazole substructures: EPC synthesis and SAR leading to a selective dopamine D4 receptor partial agonist (FAUC 179).
2001 Sep 17
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
Determination of dopamine D(4) receptor density in rat striatum using PB12 as a probe.
2001 Sep 7
Decreased [(3)H]spiperone binding in the anterior cingulate cortex of schizophrenia patients: an autoradiographic study.
2002
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
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
(+)-[76Br]A-69024: a non-benzazepine radioligand for studies of dopamine D1 receptors using PET.
2002 Apr
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
Hypothalamic paraventricular 5-hydroxytryptamine: receptor-specific inhibition of NPY-stimulated eating and energy metabolism.
2002 Apr
Physiologically identified 5-HT2-like receptors at the crayfish neuromuscular junction.
2002 Apr 5
Metachlorophenylpiperazine (m-CPP) induced intracavernous pressure responses in anaesthetized rats.
2002 Aug
Functional cooperation between neurosteroids and D2 dopamine antagonists on KCl-evoked [3H]noradrenaline release: modulation by calcium channel blockers.
2002 Dec
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
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
Novel (bisarylmethoxy)butylpiperidine analogues as neurotransmitter transporter inhibitors with activity at dopamine receptor sites.
2002 Dec
In vitro evidence that 5-hydroxytryptamine increases efflux of glial glutamate via 5-HT(2A) receptor activation.
2002 Feb 1
A novel series of hybrid compounds derived by combining 2-aminotetralin and piperazine fragments: binding activity at D2 and D3 receptors.
2002 Feb 25
Nad-299 antagonises 5-HT-stimulated and spiperone-inhibited [35S]GTPgammaS binding in cloned 5-HT1A receptors.
2002 Feb-Nov
Implementation and evaluation of a 3D one-step late reconstruction algorithm for 3D positron emission tomography brain studies using median root prior.
2002 Jan
Effects of some steroids and other compounds on ovarian growth of the red swamp crayfish, Procambarus clarkii, during early vitellogenesis.
2002 Jan 1
Functional screening of G protein-coupled receptors by measuring intracellular calcium with a fluorescence microplate reader.
2002 Jun
The human 5-HT7 serotonin receptor splice variants: constitutive activity and inverse agonist effects.
2002 Mar
The atypical 5-HT2 receptor mediating tachycardia in pithed rats: pharmacological correlation with the 5-HT2A receptor subtype.
2002 Mar
Hemiparkinsonism associated with a mesencephalic tumor.
2002 May 15
Apomorphine induces trophic factors that support fetal rat mesencephalic dopaminergic neurons in cultures.
2002 Nov
Spreading depression: imaging and blockade in the rat neocortical brain slice.
2002 Nov
Changes in electrophysiological properties of lamprey spinal motoneurons during fictive swimming.
2002 Nov
In vivo serotonin 5HT(2A) receptor binding and personality traits in healthy subjects: a positron emission tomography study.
2002 Nov
Synthesis and structure-activity relationship of the isoindolinyl benzisoxazolpiperidines as potent, selective, and orally active human dopamine D4 receptor antagonists.
2002 Oct 4
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
Corticotropin-releasing factor as well as opioid and dopamine are involved in tail-pinch-induced food intake of rats.
2003
In vivo evidence for dopamine-mediated internalization of D2-receptors after amphetamine: differential findings with [3H]raclopride versus [3H]spiperone.
2003 Feb
Characterization of the 5-hydroxytryptamine receptors mediating contraction in the pig isolated intravesical ureter.
2003 Jan
Patents

Sample Use Guides

Rat: i.v. injection 12 mkCi (180 ng).
Route of Administration: Intravenous
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
  • Download
Name Type Language
SPIPERONE
INN   JAN   MART.   MI   USAN   WHO-DD  
INN   USAN  
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
Created by admin on Sat Jun 26 14:14:15 UTC 2021 , Edited by admin on Sat Jun 26 14:14:15 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C66558
Created by admin on Sat Jun 26 14:14:15 UTC 2021 , Edited by admin on Sat Jun 26 14:14:15 UTC 2021
PRIMARY
DRUG CENTRAL
2470
Created by admin on Sat Jun 26 14:14:15 UTC 2021 , Edited by admin on Sat Jun 26 14:14:15 UTC 2021
PRIMARY
MERCK INDEX
M10148
Created by admin on Sat Jun 26 14:14:15 UTC 2021 , Edited by admin on Sat Jun 26 14:14:15 UTC 2021
PRIMARY Merck Index
EVMPD
SUB10617MIG
Created by admin on Sat Jun 26 14:14:15 UTC 2021 , Edited by admin on Sat Jun 26 14:14:15 UTC 2021
PRIMARY
MESH
D013134
Created by admin on Sat Jun 26 14:14:15 UTC 2021 , Edited by admin on Sat Jun 26 14:14:15 UTC 2021
PRIMARY
EPA CompTox
749-02-0
Created by admin on Sat Jun 26 14:14:15 UTC 2021 , Edited by admin on Sat Jun 26 14:14:15 UTC 2021
PRIMARY
ECHA (EC/EINECS)
212-024-0
Created by admin on Sat Jun 26 14:14:15 UTC 2021 , Edited by admin on Sat Jun 26 14:14:15 UTC 2021
PRIMARY
ChEMBL
CHEMBL267930
Created by admin on Sat Jun 26 14:14:15 UTC 2021 , Edited by admin on Sat Jun 26 14:14:15 UTC 2021
PRIMARY
INN
1553
Created by admin on Sat Jun 26 14:14:15 UTC 2021 , Edited by admin on Sat Jun 26 14:14:15 UTC 2021
PRIMARY
WIKIPEDIA
SPIPERONE
Created by admin on Sat Jun 26 14:14:15 UTC 2021 , Edited by admin on Sat Jun 26 14:14:15 UTC 2021
PRIMARY
CAS
749-02-0
Created by admin on Sat Jun 26 14:14:15 UTC 2021 , Edited by admin on Sat Jun 26 14:14:15 UTC 2021
PRIMARY
PUBCHEM
5265
Created by admin on Sat Jun 26 14:14:15 UTC 2021 , Edited by admin on Sat Jun 26 14:14:15 UTC 2021
PRIMARY
FDA UNII
4X6E73CJ0Q
Created by admin on Sat Jun 26 14:14:15 UTC 2021 , Edited by admin on Sat Jun 26 14:14:15 UTC 2021
PRIMARY
Related Record Type Details
LABELED -> NON-LABELED
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY