SULTOPRIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H26N2O4S
Molecular Weight	354.464
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1CCCC1CNC(=O)C2=CC(=CC=C2OC)S(=O)(=O)CC

InChI

InChIKey=UNRHXEPDKXPRTM-UHFFFAOYSA-N

InChI=1S/C17H26N2O4S/c1-4-19-10-6-7-13(19)12-18-17(20)15-11-14(24(21,22)5-2)8-9-16(15)23-3/h8-9,11,13H,4-7,10,12H2,1-3H3,(H,18,20)

HIDE SMILES / InChI

Description
Sources: https://en.wikipedia.org/wiki/Sultopride
Curator's Comment: Description was created based on several sources, including http://link.springer.com/chapter/10.1007/978-1-4613-2363-1_98

Sultopride (trade names Barnetil, Barnotil, Topral) is an atypical antipsychotic of the benzamide chemical class used in Europe, Japan, and Hong Kong for the treatment of schizophrenia. It was launched by Sanofi-Aventis in 1976. Sultopride acts as a selective D2 and D3 receptor antagonist. It has also been shown to have clinically relevant affinity for the GHB receptor as well, a property it shares in common with amisulpride and sulpiride.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16135699	Antagonist 2778		4.5 nM [IC50]
Dopamine D3 receptor 91 Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16135699	Antagonist 2778		3.8 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: http://www.exodus.co.uk/assets/pdf/CONTROLLED	Primary		Approved 8429	Barnetil Approved Use Schizophrenia Launch Date 1976
Acute and chronic psychoses 2 Sources: http://www.ndrugs.com/?s=sultopride	Primary		Approved 8429	Barnetil Approved Use Psychotic Disorders Launch Date 1976

PubMed

Title	Date	PubMed
[Arrhythmogenic effects of sultopride chlorhydrate: clinical and cellular electrophysiological correlation].	1992	1363741
Amisulpride: a review of its use in the management of schizophrenia.	2001	11735643
Atypical antipsychotics: new directions and new challenges in the treatment of schizophrenia.	2001	11160792
In vivo extrastriatal and striatal D2 dopamine receptor blockade by amisulpride in schizophrenia.	2001 Apr	11270918
[Initial experiences with amisulpride, an in Germany novel, atypical neuroleptic drug in treatment of adolescents with psychiatric disorders].	2001 Aug	11524899
(-)S amisulpride binds with high affinity to cloned dopamine D(3) and D(2) receptors.	2001 Dec 7	11740949
A single blind comparison of amisulpride, fluoxetine and clomipramine in the treatment of restricting anorectics.	2001 Jul	11444677
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	11712619
Physostigmine as treatment for severe CNS anticholinergic toxicity.	2001 Sep	11559630
Switching antipsychotic medications: general recommendations and switching to amisulpride.	2002	12201620
Amisulpride for schizophrenia.	2002	12076408
Amisulpride improves depressive symptoms in acute exacerbations of schizophrenia: comparison with haloperidol and risperidone.	2002 Aug	12126869
Dopaminergic deficit and the role of amisulpride in the treatment of schizophrenia.	2002 Dec	12685918
Dopaminergic deficit and the role of amisulpride in the treatment of mood disorders.	2002 Dec	12685917
Dose-related effects of amisulpride on five dimensions of psychopathology in patients with acute exacerbation of schizophrenia.	2002 Dec	12454554
Amisulpride, an unusual "atypical" antipsychotic: a meta-analysis of randomized controlled trials.	2002 Feb	11823257
Olanzapine-induced mania in bipolar disorders.	2002 May	12066449
Switching to amisulpride due to hepatic complications.	2002 May	12052579
Effect of the amisulpride isomers on rat catalepsy.	2002 May 24	12191584
Acute psychosis after administration of bupropion hydrochloride (Zyban).	2002 Nov	12518275
Discriminative stimulus properties in rats of the novel antipsychotic quetiapine.	2002 Nov	12498334
Amisulpride does not prevent relapse in primary alcohol dependence: results of a pilot randomized, placebo-controlled trial.	2002 Oct	12394288
Effects of sigma(1) receptor ligand MS-377 on D(2) antagonists-induced behaviors.	2002 Oct	12151023
Differential effects of high-dose amisulpride versus flupentixol on latent dimensions of depressive and negative symptomatology in acute schizophrenia: an evaluation using confirmatory factor analysis.	2002 Sep	12177587
Amisulpiride augmentation in treatment resistant obsessive-compulsive disorder: an open trial.	2003 Aug	12923825
Is regionally selective D2/D3 dopamine occupancy sufficient for atypical antipsychotic effect? an in vivo quantitative [123I]epidepride SPET study of amisulpride-treated patients.	2003 Aug	12900302
Automated determination of amisulpride by liquid chromatography with column switching and spectrophotometric detection.	2003 Feb 5	12505788
Rapid high-performance liquid chromatographic measurement of amisulpride in human plasma: application to manage acute intoxication.	2003 Jun 5	12726848
[Plasma prolactin level and incidence of adverse endocrinologic effects during therapy with atypical neuroleptics].	2003 May	14509051
Visual and auditory hallucinations with excessive intake of paroxetine.	2003 Oct	12950713
Response of catatonic schizophrenia to amisulpride: a case report.	2003 Sep	14574833
Amisulpride is an "atypical" antipsychotic associated with low weight gain.	2004 Apr	14647963
[Current pharmacotherapy of schizophrenia].	2004 Jan 18	15027331
A double-blind, randomized comparative trial of amisulpride versus olanzapine for 6 months in the treatment of schizophrenia.	2004 Mar	15076013
Serotonin reuptake inhibitor provoked recurrence of alcohol hallucinosis--remission with additive amisulpride medication. A case report.	2004 Mar	15048618
Clozapine with amisulpride for refractory schizophrenia.	2004 May	15121665
Plasma amisulpride levels in schizophrenia or schizoaffective disorder.	2004 May	15056484
Successful treatment of Tourette's disorder with amisulpride.	2004 May	15010520
Care maps: atypical antipsychotics. Introduction.	2004 May 19-25	15176111

Patents

Sample Use Guides

In Vivo Use Guide

Oral Psychoses: Adult: Acute and chronic psychoses: 400-800 mg daily. May also be given via IM inj. Oral Chronic aggression: Adult: 400-600 mg daily. Intramuscular Psychoses: Adult: Up to 800 mg daily.

Route of Administration: Oral

In Vitro Use Guide

In the presence of sultopride (30 and 100 uM) EADs (early afterdepolarisations) developed at plateau level.

Name

Type

Language

SULTOPRIDE

Official Name

English

BENZAMIDE, N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-5-(ETHYLSULFONYL)-2-METHOXY-

Systematic Name

English

Sultopride [WHO-DD]

Common Name

English

N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-5-(ETHYLSULFONYL)-2-METHOXYBENZAMIDE

Systematic Name

English

SULTOPRIDE [MI]

Common Name

English

N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-5-(ETHYLSULFONYL)-O-ANISAMIDE

Common Name

English

(±)-SULTOPRIDE

Common Name

English

sultopride [INN]

Common Name

English

(±)-N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-5-(ETHYLSULFONYL)-2-METHOXYBENZAMIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29710