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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
Amisulpride: is there a treatment for negative symptoms in schizophrenia patients?
2002
Amisulpride: progress and outcomes.
2002
Clinical implications of dopamine research in schizophrenia.
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
Amisulpride for schizophrenia.
2002
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
Gateways to clinical trials.
2002 Jan-Feb
New antipsychotic agents for schizophrenia: pharmacokinetics and metabolism update.
2002 Jul
Effect of the amisulpride isomers on rat prolactinemia.
2002 Jul 19
[Use of atypical antipsychotics in Charles Perrens psychiatric hospital (Bordeaux) analysis of prescribing practices for Amisulpride, Clozapine, Olanzapine and Risperidone].
2002 Jul-Aug
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
Switching to amisulpride due to hepatic complications.
2002 May
Tardive dyskinesias and antipsychotics: a review.
2002 May
Age-related changes in dopamine D2 receptors in rat heart and coronary vessels.
2002 May-Jun
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
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
[Frontal dysfunctions in Huntington's disease -- neuropsychology and therapy].
2003 Jan
Screening, library-assisted identification and validated quantification of fifteen neuroleptics and three of their metabolites in plasma by liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization.
2003 Mar
[Plasma prolactin level and incidence of adverse endocrinologic effects during therapy with atypical neuroleptics].
2003 May
New generation antipsychotics versus low-potency conventional antipsychotics: a systematic review and meta-analysis.
2003 May 10
Metabolic drug interactions with new psychotropic agents.
2003 Oct
Amisulpride: limbic specificity and the mechanism of antipsychotic atypicality.
2003 Oct
The antinociceptive effect of amisulpride in mice is mediated through opioid mechanisms.
2003 Oct 8
Adverse metabolic effects associated with atypical antipsychotics: literature review and clinical implications.
2004
Quetiapine. A review of its use in the management of schizophrenia.
2004
Amisulpride is an "atypical" antipsychotic associated with low weight gain.
2004 Apr
Combination of amisulpride and olanzapine in treatment-resistant schizophrenic psychoses.
2004 Feb
Combination of clozapine and amisulpride in treatment-resistant schizophrenia--case reports and review of the literature.
2004 Jan
Characterization of the effects of receptor-selective ligands in rats discriminating the novel antipsychotic quetiapine.
2004 Jan
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
Amisulpride a selective dopamine antagonist and atypical antipsychotic: results of a meta-analysis of randomized controlled trials.
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