U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Clinical advantages of amisulpride in the treatment of acute schizophrenia.
2001 Nov-Dec
Amisulpride: efficacy in the management of chronic patients with predominant negative symptoms of schizophrenia.
2001 Oct
Amisulpride: is there a treatment for negative symptoms in schizophrenia patients?
2002
A double-blind, randomised comparative trial of amisulpride versus olanzapine in the treatment of schizophrenia: short-term results at two months.
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
Amisulpride for schizophrenia.
2002
Spotlight on amisulpride in schizophrenia.
2002
Perazine for schizophrenia.
2002
A comparison of paroxetine and amisulpride in the treatment of dysthymic disorder.
2002 Aug
Dopaminergic deficit and the role of amisulpride in the treatment of mood disorders.
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
Atypical antipsychotics: mechanism of action.
2002 Feb
Amisulpride, an unusual "atypical" antipsychotic: a meta-analysis of randomized controlled trials.
2002 Feb
Comparative efficacy of SSRIs and amisulpride in burning mouth syndrome: a single-blind study.
2002 Jan
Social functioning and quality of life in the schizophrenic patient: advantages of amisulpride.
2002 Jan
New antipsychotic agents for schizophrenia: pharmacokinetics and metabolism update.
2002 Jul
The glial growth factors deficiency and synaptic destabilization hypothesis of schizophrenia.
2002 Jul 3
[Use of atypical antipsychotics in Charles Perrens psychiatric hospital (Bordeaux) analysis of prescribing practices for Amisulpride, Clozapine, Olanzapine and Risperidone].
2002 Jul-Aug
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
A systematic review of the use of atypical antipsychotics in autism.
2002 Mar
[Pharmaco-epidemiological study on antipsychotic drug prescription in French Psychiatry: Patient characteristics, antipsychotic treatment, and care management for schizophrenia].
2002 Mar-Apr
Neuroleptic malignant syndrome due to atypical neuroleptics: three episodes in one patient.
2002 May
Gateways to clinical trials.
2002 May
Effect of the amisulpride isomers on rat catalepsy.
2002 May 24
Age-related changes in dopamine D2 receptors in rat heart and coronary vessels.
2002 May-Jun
A comparison of paroxetine versus paroxetine plus amisulpride in the treatment of dysthymic disorder: efficacy and psychosocial outcomes.
2002 Oct 10
New generation antipsychotics for first episode schizophrenia.
2003
Benefits and risks of pharmacotherapy for dysthymia: a systematic appraisal of the evidence.
2003
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
Respective roles of dopamine D2 and D3 receptors in food-seeking behaviour in rats.
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
Quantification of D2-like dopamine receptors in the human brain with 18F-desmethoxyfallypride.
2003 Jan
Lack of effect of amisulpride on the pharmacokinetics and safety of lithium.
2003 Jun
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
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
Response of catatonic schizophrenia to amisulpride: a case report.
2003 Sep
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
Combination of clozapine and amisulpride in treatment-resistant schizophrenia--case reports and review of the literature.
2004 Jan
Evidence-based pharmacotherapy of schizophrenia.
2004 Jun
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
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