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Details

Stereochemistry RACEMIC
Molecular Formula C17H26N2O4S.ClH
Molecular Weight 390.925
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULTOPRIDE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=IGOWMQPOGQYFFM-UHFFFAOYSA-N
InChI=1S/C17H26N2O4S.ClH/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);1H

HIDE SMILES / InChI

Description
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

CNS Penetrant
2588
Curator's Comment: Sultopride passes the blood-brain barrier in rats

Originator

Delagrange
9
Curator's Comment: Discovered in DELAGRANGE Laboratory in 1965

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 4.5 nM [IC50]
Antagonist
2849
 3.8 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Barnetil

Approved Use

Schizophrenia

Launch Date

1976
Primary
Approved
8583
Barnetil

Approved Use

Psychotic Disorders

Launch Date

1976
PubMed

PubMed

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

Patents

20040082653
5
CN104447476B
2
CN104744332A
2
CN1315804C
2
JP3408158B2
2
JPS57203955A
4
US20140206667A1
2

Sample Use Guides

In Vivo Use Guide
Curator's Comment: May also be given via IM injection
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 HYDROCHLORIDE
MI   WHO-DD  
Common Name English
BARNETIL
Preferred Name English
BARNOTIL
Brand Name English
SULTOPRIDE HYDROCHLORIDE [JAN]
Common Name English
N-(1-ETHYL-2-PYRROLIDINYLMETHYL)-2-METHOXY-5-(ETHYLSULFONYL)BENZAMIDE HYDROCHLORIDE
Systematic Name English
Sultopride hydrochloride [WHO-DD]
Common Name English
BENZAMIDE, N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-5-(ETHYLSULFONYL)-2-METHOXY-, HYDROCHLORIDE (1:1)
Systematic Name English
SULTOPRIDE HYDROCHLORIDE [MI]
Common Name English
BENZAMIDE, N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-5-(ETHYLSULFONYL)-2-METHOXY-, MONOHYDROCHLORIDE
Common Name English
N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-5-(ETHYLSULFONYL)-2-METHOXYBENZAMIDE HYDROCHLORIDE
Systematic Name English
LIN-1418
Code English
O-ANISAMIDE, N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-5-(ETHYLSULFONYL)-, MONOHYDROCHLORIDE
Common Name English
Code System Code Type Description
EVMPD
SUB04647MIG
Created by admin on Mon Mar 31 20:51:02 GMT 2025 , Edited by admin on Mon Mar 31 20:51:02 GMT 2025
PRIMARY
CAS
23694-17-9
Created by admin on Mon Mar 31 20:51:02 GMT 2025 , Edited by admin on Mon Mar 31 20:51:02 GMT 2025
PRIMARY
PUBCHEM
41485
Created by admin on Mon Mar 31 20:51:02 GMT 2025 , Edited by admin on Mon Mar 31 20:51:02 GMT 2025
PRIMARY
DRUG BANK
DBSALT002916
Created by admin on Mon Mar 31 20:51:02 GMT 2025 , Edited by admin on Mon Mar 31 20:51:02 GMT 2025
PRIMARY
ECHA (EC/EINECS)
245-829-0
Created by admin on Mon Mar 31 20:51:02 GMT 2025 , Edited by admin on Mon Mar 31 20:51:02 GMT 2025
PRIMARY
SMS_ID
100000084767
Created by admin on Mon Mar 31 20:51:02 GMT 2025 , Edited by admin on Mon Mar 31 20:51:02 GMT 2025
PRIMARY
MERCK INDEX
m10393
Created by admin on Mon Mar 31 20:51:02 GMT 2025 , Edited by admin on Mon Mar 31 20:51:02 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL277945
Created by admin on Mon Mar 31 20:51:02 GMT 2025 , Edited by admin on Mon Mar 31 20:51:02 GMT 2025
PRIMARY
RXCUI
236185
Created by admin on Mon Mar 31 20:51:02 GMT 2025 , Edited by admin on Mon Mar 31 20:51:02 GMT 2025
PRIMARY RxNorm
FDA UNII
8Q6926T32J
Created by admin on Mon Mar 31 20:51:02 GMT 2025 , Edited by admin on Mon Mar 31 20:51:02 GMT 2025
PRIMARY
EPA CompTox
DTXSID0049070
Created by admin on Mon Mar 31 20:51:02 GMT 2025 , Edited by admin on Mon Mar 31 20:51:02 GMT 2025
PRIMARY
PARENT (SALT/SOLVATE)
Structure of SULTOPRIDE
NIH
NCATS
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