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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

2020
57
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2491
Schizophrenia
 3.2 nM [Ki]
Antagonist
2491
Schizophrenia
 11.5 nM [Ki]
Antagonist
2491
Schizophrenia
 13.0 nM [Ki]
Antagonist
2491
Schizophrenia
 2.8 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Serotonin 7 (5-HT7) receptor
Dopamine D3 receptor
Serotonin 2b (5-HT2b) receptor
Dopamine D2 receptor
Approved
7883
SOLIAN
Approved (off-label)
8
PubMed

PubMed

TitleDatePubMed
Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor.
1992 Apr 10
Extrastriatal and striatal D(2) dopamine receptor blockade with haloperidol or new antipsychotic drugs in patients with schizophrenia.
2001 Dec
Effects of newer atypical antipsychotics on autonomic neurocardiac function: a comparison between amisulpride, olanzapine, sertindole, and clozapine.
2001 Feb
Asymptomatic bradycardia associated with amisulpride.
2001 Nov
Amisulpride: efficacy in the management of chronic patients with predominant negative symptoms of schizophrenia.
2001 Oct
Switching antipsychotic medications: general recommendations and switching to amisulpride.
2002
Amisulpride for schizophrenia.
2002
Spotlight on amisulpride in schizophrenia.
2002
Effects of newer antipsychotics on extrapyramidal function.
2002
A comparison of paroxetine and amisulpride in the treatment of dysthymic disorder.
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
Effects of amisulpride on consummatory negative contrast.
2002 Dec
Atypical antipsychotics: mechanism of action.
2002 Feb
A review of the pharmacokinetics, tolerability and pharmacodynamics of amisulpride in healthy volunteers.
2002 Jan
New antipsychotic agents for schizophrenia: pharmacokinetics and metabolism update.
2002 Jul
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
Gateways to clinical trials.
2002 May
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
Respective roles of dopamine D2 and D3 receptors in food-seeking behaviour in rats.
2003 Feb
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
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
Amisulpride is an "atypical" antipsychotic associated with low weight gain.
2004 Apr
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
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
Patents

Patents

JP2001501192A
2
JP2002527464A
2
JP4178032B2
6

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
Structure of AMISULPRIDE, (S)-
ENANTIOMER -> RACEMATE
Structure of AMISULPRIDE, (R)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of N-METHYL AMISULPRIDE
IMPURITY -> PARENT
Related Record Type Details
Structure of AMISULPRIDE
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