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Details

Stereochemistry RACEMIC
Molecular Formula C17H27N3O4S
Molecular Weight 369.479
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMISULPRIDE

SMILES

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

InChI

InChIKey=NTJOBXMMWNYJFB-UHFFFAOYSA-N
InChI=1S/C17H27N3O4S/c1-4-20-8-6-7-12(20)11-19-17(21)13-9-16(25(22,23)5-2)14(18)10-15(13)24-3/h9-10,12H,4-8,11,18H2,1-3H3,(H,19,21)

HIDE SMILES / InChI

Description

Amisulpride, a benzamide derivative, shows a unique therapeutic profile being atypical antipsychotic. At low doses, it enhances dopaminergic neurotransmission by preferentially blocking presynaptic dopamine D2/D3 autoreceptors. At higher doses, amisupride antagonises postsynaptic dopamine D2 and D3 receptors, preferentially in the limbic system rather than the striatum, thereby reducing dopaminergic transmission. In addition its antagonism at serotonin 5-HT7 receptors likely underlies the antidepressant actions. Amisulpride is approved for clinical use in treating schizophrenia in a number of European countries and also for treating dysthymia, a mild form of depression, in Italy.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor.
1992 Apr 10
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
Long-term effects of the substituted benzamide derivative amisulpride on baseline and stimulated prolactin levels.
2002
Switching antipsychotic medications: general recommendations and switching to amisulpride.
2002
Focus on amisulpride.
2002
Amisulpride for schizophrenia.
2002
Review: amisulpride is effective and safe for schizophrenia.
2002 Aug
A comparison of paroxetine and amisulpride in the treatment of dysthymic disorder.
2002 Aug
Amisulpride improves depressive symptoms in acute exacerbations of schizophrenia: comparison with haloperidol and risperidone.
2002 Aug
SPECT imaging, clinical features, and cognition before and after low doses of amisulpride in schizophrenic patients with the deficit syndrome.
2002 Aug 20
Liver function tests during treatment with antipsychotic drugs: a case series of 23 patients.
2002 Dec
Effects of amisulpride on consummatory negative contrast.
2002 Dec
Amisulpride vs. risperidone in chronic schizophrenia: results of a 6-month double-blind study.
2002 Dec
Dose-related effects of amisulpride on five dimensions of psychopathology in patients with acute exacerbation of schizophrenia.
2002 Dec
New antipsychotic agents for schizophrenia: pharmacokinetics and metabolism update.
2002 Jul
Effect of the amisulpride isomers on rat prolactinemia.
2002 Jul 19
The glial growth factors deficiency and synaptic destabilization hypothesis of schizophrenia.
2002 Jul 3
Variations in prescribing atypical antipsychotic drugs in primary care: cross-sectional study.
2002 Jun
Striatal dopamine-2 receptor occupancy as measured with [123I]iodobenzamide and SPECT predicted the occurrence of EPS in patients treated with atypical antipsychotics and haloperidol.
2002 Jun
Carmoxirole is able to reduce amisulpride-induced hyperprolactinemia without affecting its central effect.
2002 Jun 28
Neuroleptic malignant syndrome due to atypical neuroleptics: three episodes in one patient.
2002 May
Tardive dyskinesias and antipsychotics: a review.
2002 May
Effect of the amisulpride isomers on rat catalepsy.
2002 May 24
Discriminative stimulus properties in rats of the novel antipsychotic quetiapine.
2002 Nov
Amisulpride does not prevent relapse in primary alcohol dependence: results of a pilot randomized, placebo-controlled trial.
2002 Oct
A comparison of paroxetine versus paroxetine plus amisulpride in the treatment of dysthymic disorder: efficacy and psychosocial outcomes.
2002 Oct 10
The differential effects of atypical antipsychotics on prolactin elevation are explained by their differential blood-brain disposition: a pharmacological analysis in rats.
2002 Sep
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
New generation antipsychotics for first episode schizophrenia.
2003
Benefits and risks of pharmacotherapy for dysthymia: a systematic appraisal of the evidence.
2003
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
Analysis of eighteen antidepressants, four atypical antipsychotics and active metabolites in serum by liquid chromatography: a simple tool for therapeutic drug monitoring.
2003 Aug 25
Which neuroleptic would psychiatrists take for themselves or their relatives?
2003 Feb
Automated determination of amisulpride by liquid chromatography with column switching and spectrophotometric detection.
2003 Feb 5
Amisulpride versus risperidone in the treatment of schizophrenic patients: a double-blind pilot study in Taiwan.
2003 Jan
Lack of effect of amisulpride on the pharmacokinetics and safety of lithium.
2003 Jun
Rapid high-performance liquid chromatographic measurement of amisulpride in human plasma: application to manage acute intoxication.
2003 Jun 5
The new and evolving pharmacotherapy of schizophrenia.
2003 Mar
How does the benzamide antipsychotic amisulpride get into the brain?--An in vitro approach comparing amisulpride with clozapine.
2003 Nov
Adverse metabolic effects associated with atypical antipsychotics: literature review and clinical implications.
2004
Amisulpride is an "atypical" antipsychotic associated with low weight gain.
2004 Apr
Evidence-based pharmacotherapy of schizophrenia.
2004 Jun
Dopaminergic receptors in rat dura mater: pharmacological characteristics.
2004 Mar
Dosage finding and outcome in the treatment of schizophrenic inpatients with amisulpride. Results of a drug utilization observation study.
2004 Mar
Lower risk for tardive dyskinesia associated with second-generation antipsychotics: a systematic review of 1-year studies.
2004 Mar
How do we choose between atypical antipsychotics? The advantages of amisulpride.
2004 Mar
Successful treatment of Tourette's disorder with amisulpride.
2004 May
Prolactinemia is uncoupled from central D2/D3 dopamine receptor occupancy in amisulpride treated patients.
2004 Sep
Patents

Sample Use Guides

In Vivo Use Guide
For acute psychotic episodes, oral doses between 400 mg/d and 800 mg/d are recommended. In individual cases, the daily dose may be increased up to 1200 mg/d. Doses above 1200 mg/d have not been extensively evaluated for safety and therefore should not be used. Doses above 800 mg/d have not been shown to be superior to lower doses and may increase the incidence of adverse events. No specific titration is required when initiating the treatment with amisulpride. Doses should be adjusted according to individual response.
Route of Administration: Oral
In Vitro Use Guide
In NG108-15 cells stably transfected with the human D3 dopamine receptor amisulpride inhibited quinpirole-elicited mitogenesis with an IC50 value of 22 nM
Name Type Language
AMISULPRIDE
EP   INN   MART.   MI   WHO-DD  
INN  
Official Name English
APD421
Code English
AMISULPRIDE [EP]
Common Name English
BENZAMIDE, 4-AMINO-N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-5-(ETHYLSULFONYL)-2-METHOXY-
Systematic Name English
SULAMID
Brand Name English
AMISULPRIDE [WHO-DD]
Common Name English
DAN-2163
Code English
AMISULPRIDE [MI]
Common Name English
APD-421
Code English
SOLIAN
Brand Name English
DENIBAN
Brand Name English
(+/-)-AMISULPRIDE
Common Name English
SOCIAN
Brand Name English
AMISULPRIDE [MART.]
Common Name English
4-AMINO-N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-5-(ETHYLSULFONYL)-O-ANISAMIDE
Common Name English
AMISULPRIDE [INN]
Common Name English
AMINOSULTOPRIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66883
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
WHO-VATC QN05AL05
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
WHO-ATC N05AL05
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
Code System Code Type Description
EVMPD
SUB05458MIG
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
PRIMARY
INN
4960
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
PRIMARY
NCI_THESAURUS
C83533
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
PRIMARY
WIKIPEDIA
AMISULPRIDE
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
PRIMARY
DRUG BANK
DB06288
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
PRIMARY
ChEMBL
CHEMBL243712
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
PRIMARY
MERCK INDEX
M1751
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
PRIMARY Merck Index
CAS
71675-85-9
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
PRIMARY
ECHA (EC/EINECS)
275-831-7
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
PRIMARY
IUPHAR
963
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
PRIMARY
PUBCHEM
2159
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
PRIMARY
RXCUI
46303
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
PRIMARY RxNorm
EPA CompTox
71675-85-9
Created by admin on Tue Oct 22 00:18:40 UTC 2019 , Edited by admin on Tue Oct 22 00:18:40 UTC 2019
PRIMARY