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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
Adverse metabolic effects associated with atypical antipsychotics: literature review and clinical implications.
2004
Combination of amisulpride and olanzapine in treatment-resistant schizophrenic psychoses.
2004 Feb
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
WHO-VATC QN05AL05
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
WHO-ATC N05AL05
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
Code System Code Type Description
EVMPD
SUB05458MIG
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
PRIMARY
INN
4960
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
PRIMARY
NCI_THESAURUS
C83533
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
PRIMARY
WIKIPEDIA
AMISULPRIDE
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
PRIMARY
DRUG BANK
DB06288
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
PRIMARY
ChEMBL
CHEMBL243712
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
PRIMARY
MERCK INDEX
M1751
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
PRIMARY Merck Index
CAS
71675-85-9
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
PRIMARY
ECHA (EC/EINECS)
275-831-7
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
PRIMARY
IUPHAR
963
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
PRIMARY
PUBCHEM
2159
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
PRIMARY
RXCUI
46303
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
PRIMARY RxNorm
EPA CompTox
71675-85-9
Created by admin on Tue Mar 06 12:34:35 UTC 2018 , Edited by admin on Tue Mar 06 12:34:35 UTC 2018
PRIMARY