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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

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

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
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
Switching to amisulpride.
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
SPECT imaging, clinical features, and cognition before and after low doses of amisulpride in schizophrenic patients with the deficit syndrome.
2002 Aug 20
Dopaminergic deficit and the role of amisulpride in the treatment of schizophrenia.
2002 Dec
Liver function tests during treatment with antipsychotic drugs: a case series of 23 patients.
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
Effect of the amisulpride isomers on rat prolactinemia.
2002 Jul 19
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
Switching to amisulpride due to hepatic complications.
2002 May
Tardive dyskinesias and antipsychotics: a review.
2002 May
Effect of the amisulpride isomers on rat catalepsy.
2002 May 24
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
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
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
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
How does the benzamide antipsychotic amisulpride get into the brain?--An in vitro approach comparing amisulpride with clozapine.
2003 Nov
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
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 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
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
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:18:40 UTC 2019
Edited
by admin
on Tue Oct 22 00:18:40 UTC 2019
Record UNII
8110R61I4U
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY