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Details

Stereochemistry RACEMIC
Molecular Formula C15H23N3O4S.ClH
Molecular Weight 377.887
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULPIRIDE HYDROCHLORIDE

SMILES

Cl.CCN1CCCC1CNC(=O)C2=C(OC)C=CC(=C2)S(N)(=O)=O

InChI

InChIKey=PFHZICSPLHQCDZ-UHFFFAOYSA-N
InChI=1S/C15H23N3O4S.ClH/c1-3-18-8-4-5-11(18)10-17-15(19)13-9-12(23(16,20)21)6-7-14(13)22-2;/h6-7,9,11H,3-5,8,10H2,1-2H3,(H,17,19)(H2,16,20,21);1H

HIDE SMILES / InChI

Molecular Formula C15H23N3O4S
Molecular Weight 341.426
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
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/6628519

Sulpiride is an atypical antipsychotic drug (although some texts have referred to it as a typical antipsychotic) of the benzamide class used mainly in the treatment of psychosis associated with schizophrenia and major depressive disorder, and sometimes used in low dosage to treat anxiety and mild depression. Sulpiride is commonly used in Europe, Russia and Japan. Sulpiride is a selective antagonist at dopamine D2 and D3 receptors. This action dominates in doses exceeding 600 mg daily. In doses of 600 to 1,600 mg sulpiride shows mild sedating and antipsychotic activity. Its antipsychotic potency compared to chlorpromazine is only 0.2 (1/5). In low doses (in particular 50 to 200 mg daily) its prominent feature is antagonism of presynaptic inhibitory dopamine receptors accounting for some antidepressant activity and a stimulating effect. Therefore, it is in these doses used as a second line antidepressant. Racemic and L-sulpiride significantly decreased stimulated serum gastrin concentration, but they did not affect fasting serum gastrin or basal and stimulated gastric acidity. D-sulpiride significantly decreased gastric acid secretion, without affecting serum gastrin levels.

Originator

Sources: Comptes Rendus des Seances de l'Academie des Sciences, Serie D: Sciences Naturelles (1967), 265, (17), 1253-4

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
10.28 nM [IC50]
66.22 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Eglonyl

Approved Use

Indications. Acute and chronic psychosis (confusion, delirium, confusion, agrammatism, abulia), schizophrenia; neurotic state, accompanied by lethargy; psychosomatic symptoms (especially for stomach ulcers and duodenal ulcers and hemorrhagic rektokolite).
Primary
Eglonyl

Approved Use

Indications. Acute and chronic psychosis (confusion, delirium, confusion, agrammatism, abulia), schizophrenia; neurotic state, accompanied by lethargy; psychosomatic symptoms (especially for stomach ulcers and duodenal ulcers and hemorrhagic rektokolite).
PubMed

PubMed

TitleDatePubMed
The role of the globus pallidus D2 subfamily of dopamine receptors in pallidal immediate early gene expression.
2001
Short-term modulation of prolactin secretion by melatonin in anestrous ewes following dopamine- and opiate receptor blockade.
2001
Consensus on the Practical Use of Amisulpride, an Atypical Antipsychotic, in the Treatment of Schizophrenia.
2001
[Initial experiences with amisulpride, an in Germany novel, atypical neuroleptic drug in treatment of adolescents with psychiatric disorders].
2001 Aug
Atypical neuroleptic drugs downregulate dopamine sensitivity in rat cortical and striatal astrocytes.
2001 Aug
A method to evaluate the diffusion rate of drugs from a microdialysis probe through brain tissue.
2001 Aug 15
Dopamine D1 and NMDA receptors mediate potentiation of basolateral amygdala-evoked firing of nucleus accumbens neurons.
2001 Aug 15
Amphetamine distorts stimulation-dependent dopamine overflow: effects on D2 autoreceptors, transporters, and synaptic vesicle stores.
2001 Aug 15
Effects of kappa-opioid receptor agonists on long-term cocaine use and dopamine neurotransmission.
2001 Aug 24
A dopaminergic mechanism is involved in the 'anxiogenic-like' response induced by chronic amphetamine treatment: a behavioral and neurochemical study.
2001 Aug 3
Intra-supraoptic nucleus sulpiride improves anorexia in tumor-bearing rats.
2001 Aug 8
Hypothalamic dopaminergic receptor expressions in anorexia of tumor-bearing rats.
2001 Dec
[Participation of the dopaminergic brain system in effects of glucocorticoid hormones].
2001 Jul
D2-like dopamine receptor activation excites rat dorsal raphe 5-HT neurons in vitro.
2001 Jul
Dopamine D2 receptor mediated presynaptic inhibition of striatopallidal GABA(A) IPSCs in vitro.
2001 Jul
A single blind comparison of amisulpride, fluoxetine and clomipramine in the treatment of restricting anorectics.
2001 Jul
Adenosine A2A agonist CGS 21680 decreases the affinity of dopamine D2 receptors for dopamine in human striatum.
2001 Jul 3
Sulpiride in the treatment of somatoform disorders: results of a European observational study to characterize the responder profile.
2001 Jul-Aug
[Anti-stress effect of nitric oxide].
2001 Jul-Aug
[Pseudoneurotic schizophrenia: a case report].
2001 Jul-Aug
Pharmacological characterization of the D1- and D2-like dopamine receptors from the brain of the leopard frog, Rana pipiens.
2001 Jun
Neuroendocrine responsivities of the pituitary dopamine system in male schizophrenic patients during treatment with clozapine, olanzapine, risperidone, sulpiride, or haloperidol.
2001 Jun
The role of medial prefrontal cortical dopamine in spontaneous flexibility in the rat.
2001 Jun
The prolactin response to sulpiride in major depression: the role of the D2 receptor in depression.
2001 Jun
Accumbens dopamine mechanisms in sucrose intake.
2001 Jun 15
Dopamine D2-like receptors and amino acid-induced glomerular hyperfiltration in humans.
2001 May
Attenuation of morphine dependence and withdrawal in rats by venlafaxine, a serotonin and noradrenaline reuptake inhibitor.
2001 May 25
Faster response on amisulpride 50 mg versus sertraline 50-100 mg in patients with dysthymia or double depression: a randomized, double-blind, parallel group study.
2001 Nov
Dopaminergic modulation of grooming behavior in virgin and pregnant rats.
2001 Nov
Involvement of serotonergic and dopaminergic mechanisms in hyperthermia induced by a serotonin-releasing drug, p-chloroamphetamine in mice.
2001 Nov 2
Postnatal decrease of sodium current density in rat pituitary melanotropes following the onset of dopaminergic innervation.
2001 Nov 27
Dopaminergic and cholinergic antagonism in a novel-object detection task with rats.
2001 Nov 29
Development of a high-performance liquid chromatographic method for bioanalytical applications with sulpiride.
2001 Nov 5
Prevalence of obesity in adolescent and young adult patients with and without schizophrenia and in relationship to antipsychotic medication.
2001 Nov-Dec
Catalepsy induced by a blockade of dopamine D1 or D2 receptors was reversed by a concomitant blockade of adenosine A(2A) receptors in the caudate-putamen of rats.
2001 Oct
Dopamine mediates striatal malonate toxicity via dopamine transporter-dependent generation of reactive oxygen species and D2 but not D1 receptor activation.
2001 Oct
The effects of dopamine and its antagonists on directional delay-period activity of prefrontal neurons in monkeys during an oculomotor delayed-response task.
2001 Oct
Characterization of the role of medial prefrontal cortex dopamine receptors in cocaine-induced locomotor activity.
2001 Oct
Inverse agonist actions of typical and atypical antipsychotic drugs at the human 5-hydroxytryptamine(2C) receptor.
2001 Oct
Changes in muscle tone are regulated by D1 and D2 dopamine receptors in the ventral striatum and D1 receptors in the substantia nigra.
2001 Oct
Novel Ca2+ dependence and time course of somatodendritic dopamine release: substantia nigra versus striatum.
2001 Oct 1
Potentiation of opioid analgesia in dopamine2 receptor knock-out mice: evidence for a tonically active anti-opioid system.
2001 Oct 1
Hypothalamic CRH mRNA levels are differentially modulated by repeated 'binge' cocaine with or without D(1) dopamine receptor blockade.
2001 Oct 19
Detection of pharmacologically mediated changes in cerebral activity by functional magnetic resonance imaging: the effects of sulpiride in the brain of the anaesthetised rat.
2001 Oct 19
Modulation of dopamine uptake in rat nucleus accumbens: effect of specific dopamine receptor antagonists and sigma ligands.
2001 Oct 26
[Incompatibility of olanzapine and amisulpride in multisystemic myotonic myopathy].
2001 Sep
Physostigmine as treatment for severe CNS anticholinergic toxicity.
2001 Sep
Dopamine D4 receptor activation inhibits presynaptically glutamatergic neurotransmission in the rat supraoptic nucleus.
2001 Sep
Differential time-course profiles of dopamine release and uptake changes induced by three dopamine uptake inhibitors.
2001 Sep 15
Repeated treatment with imipramine, fluvoxamine and tranylcypromine decreases the number of escape failures by activating dopaminergic systems in a rat learned helplessness test.
2001 Sep 7
Patents

Sample Use Guides

400mg twice daily the doctor may reduce the dose to 200mg twice daily or increase it to a maximum of 1200mg twice daily
Route of Administration: Oral
CHO-K1 D3R cells (DiscoveRx) were seeded at a density of 5000 cells/well in 384-well black, clear-bottom plates. Following 24 h of incubation, the cells were treated with multiple concentrations of the Sulpiride (0-10 μM) in Hanks’ balanced buffer solution containing 2% DMSO. Following a 10 min preincubation, the cells were next treated with an EC95 dose of dopamine (100 nM) and then incubated at 37 C for 90 min. DiscoveRx reagent (2.5) was then added to cells followed by a 60 min incubation at room temperature. Luminescence was measured on a Hamamatsu FDSS μ-cell reader.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:33:01 UTC 2023
Edited
by admin
on Sat Dec 16 11:33:01 UTC 2023
Record UNII
03U3QUS07J
Record Status Validated (UNII)
Record Version
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Name Type Language
SULPIRIDE HYDROCHLORIDE
Common Name English
SULPIRIDE MONOHYDROCHLORIDE
Common Name English
N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-2-METHOXY-5-SULFAMOYLBENZAMIDE HYDROCHLORIDE
Systematic Name English
BENZAMIDE, 5-(AMINOSULFONYL)-N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-2-METHOXY-, HYDROCHLORIDE (1:1)
Systematic Name English
BENZAMIDE, 5-(AMINOSULFONYL)-N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-2-METHOXY-, MONOHYDROCHLORIDE
Common Name English
O-ANISAMIDE, N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-5-SULFAMOYL-, MONOHYDROCHLORIDE
Common Name English
Code System Code Type Description
CAS
23694-14-6
Created by admin on Sat Dec 16 11:33:01 UTC 2023 , Edited by admin on Sat Dec 16 11:33:01 UTC 2023
PRIMARY
ECHA (EC/EINECS)
245-826-4
Created by admin on Sat Dec 16 11:33:01 UTC 2023 , Edited by admin on Sat Dec 16 11:33:01 UTC 2023
PRIMARY
EPA CompTox
DTXSID80946497
Created by admin on Sat Dec 16 11:33:01 UTC 2023 , Edited by admin on Sat Dec 16 11:33:01 UTC 2023
PRIMARY
CAS
74586-15-5
Created by admin on Sat Dec 16 11:33:01 UTC 2023 , Edited by admin on Sat Dec 16 11:33:01 UTC 2023
NON-SPECIFIC STOICHIOMETRY
FDA UNII
03U3QUS07J
Created by admin on Sat Dec 16 11:33:01 UTC 2023 , Edited by admin on Sat Dec 16 11:33:01 UTC 2023
PRIMARY
CAS
74686-71-8
Created by admin on Sat Dec 16 11:33:01 UTC 2023 , Edited by admin on Sat Dec 16 11:33:01 UTC 2023
SUPERSEDED
PUBCHEM
3015163
Created by admin on Sat Dec 16 11:33:01 UTC 2023 , Edited by admin on Sat Dec 16 11:33:01 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE