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

Molecular Formula	C17H26N2O4S
Molecular Weight	354.464
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 311 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16135699	Antagonist 2849		4.5 nM [IC50]
Dopamine D3 receptor 97 Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16135699	Antagonist 2849		3.8 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 305 Sources: http://www.exodus.co.uk/assets/pdf/CONTROLLED	Primary		Approved 8583	Barnetil Approved Use Schizophrenia Launch Date 1976
Acute and chronic psychoses 2 Sources: http://www.ndrugs.com/?s=sultopride	Primary		Approved 8583	Barnetil Approved Use Psychotic Disorders Launch Date 1976

PubMed

Title	Date	PubMed
Prolactinemia is uncoupled from central D2/D3 dopamine receptor occupancy in amisulpride treated patients.	2004-09	14997280
Care maps: atypical antipsychotics. Introduction.	2004-06-05	15176111
Clozapine with amisulpride for refractory schizophrenia.	2004-05	15121665
Plasma amisulpride levels in schizophrenia or schizoaffective disorder.	2004-05	15056484
Successful treatment of Tourette's disorder with amisulpride.	2004-05	15010520
Quetiapine-associated acute dystonia.	2004-04	14966260
Amisulpride is an "atypical" antipsychotic associated with low weight gain.	2004-04	14647963
A double-blind, randomized comparative trial of amisulpride versus olanzapine for 6 months in the treatment of schizophrenia.	2004-03	15076013
Serotonin reuptake inhibitor provoked recurrence of alcohol hallucinosis--remission with additive amisulpride medication. A case report.	2004-03	15048618
Dosage finding and outcome in the treatment of schizophrenic inpatients with amisulpride. Results of a drug utilization observation study.	2004-03	14994321
Lower risk for tardive dyskinesia associated with second-generation antipsychotics: a systematic review of 1-year studies.	2004-03	14992963
How do we choose between atypical antipsychotics? The advantages of amisulpride.	2004-03	14972081
Amisulpride a selective dopamine antagonist and atypical antipsychotic: results of a meta-analysis of randomized controlled trials.	2004-03	14972080
Combination of amisulpride and olanzapine in treatment-resistant schizophrenic psychoses.	2004-02	14969782
[Current pharmacotherapy of schizophrenia].	2004-01-18	15027331
Combination of clozapine and amisulpride in treatment-resistant schizophrenia--case reports and review of the literature.	2004-01	14750045
How does the benzamide antipsychotic amisulpride get into the brain?--An in vitro approach comparing amisulpride with clozapine.	2003-11	12865899
The antinociceptive effect of amisulpride in mice is mediated through opioid mechanisms.	2003-10-08	14575800
Amisulpride: limbic specificity and the mechanism of antipsychotic atypicality.	2003-10	14642970
Visual and auditory hallucinations with excessive intake of paroxetine.	2003-10	12950713
Response of catatonic schizophrenia to amisulpride: a case report.	2003-09	14574833
Amisulpiride augmentation in treatment resistant obsessive-compulsive disorder: an open trial.	2003-08	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.	2003-08	12900302
Amisulpride-induced mania in a patient with schizophrenia.	2003-08	12893676
Rapid high-performance liquid chromatographic measurement of amisulpride in human plasma: application to manage acute intoxication.	2003-06-05	12726848
Lack of effect of amisulpride on the pharmacokinetics and safety of lithium.	2003-06	12890302
Pharmacological approaches to the management of schizophrenia.	2003-05-05	12720524
[Plasma prolactin level and incidence of adverse endocrinologic effects during therapy with atypical neuroleptics].	2003-05	14509051
Direct determination of benzamides in serum by column-switching high-performance liquid chromatography.	2003-05	12769385
Automated determination of amisulpride by liquid chromatography with column switching and spectrophotometric detection.	2003-02-05	12505788
Amisulpride versus risperidone in the treatment of schizophrenic patients: a double-blind pilot study in Taiwan.	2003-01	12684609
[Frontal dysfunctions in Huntington's disease -- neuropsychology and therapy].	2003-01	12524580
Dopaminergic deficit and the role of amisulpride in the treatment of schizophrenia.	2002-12	12685918
Dopaminergic deficit and the role of amisulpride in the treatment of mood disorders.	2002-12	12685917
Foreword. The clinical aspects of deficit in dopaminergic ways.	2002-12	12685915
Effects of amisulpride on consummatory negative contrast.	2002-12	12478217
Amisulpride vs. risperidone in chronic schizophrenia: results of a 6-month double-blind study.	2002-12	12464464
Dose-related effects of amisulpride on five dimensions of psychopathology in patients with acute exacerbation of schizophrenia.	2002-12	12454554
Acute psychosis after administration of bupropion hydrochloride (Zyban).	2002-11	12518275
Discriminative stimulus properties in rats of the novel antipsychotic quetiapine.	2002-11	12498334
A comparison of paroxetine versus paroxetine plus amisulpride in the treatment of dysthymic disorder: efficacy and psychosocial outcomes.	2002-10-10	12429360
Amisulpride does not prevent relapse in primary alcohol dependence: results of a pilot randomized, placebo-controlled trial.	2002-10	12394288
A review of the pharmacokinetics, tolerability and pharmacodynamics of amisulpride in healthy volunteers.	2002-01	12404702
[Schizoaffective disorder: clinical symptoms and present-day approach to treatment].	2002	12532717
A double-blind, randomised comparative trial of amisulpride versus olanzapine in the treatment of schizophrenia: short-term results at two months.	2002	12442883
Switching to amisulpride.	2002	12418609
Amisulpride: progress and outcomes.	2002	12418608
Clinical implications of dopamine research in schizophrenia.	2002	12418605
Neuroleptics and family history of Parkinson diseases: case report.	2001-05	12690781
[Arrhythmogenic effects of sultopride chlorhydrate: clinical and cellular electrophysiological correlation].	1992	1363741

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:00:57 GMT 2025` Edited by `admin` on `Mon Mar 31 18:00:57 GMT 2025`
Record UNII	AA0G3TW31W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SULTOPRIDE

Official Name

English

(±)-SULTOPRIDE

Preferred 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 [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