AMISULPRIDE

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 Search

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

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D3 receptor 82	Antagonist 2491	Schizophrenia	3.2 nM [Ki]
Serotonin 7 (5-HT7) receptor 22	Antagonist 2491	Schizophrenia	11.5 nM [Ki]
Serotonin 2b (5-HT2b) receptor 50	Antagonist 2491	Schizophrenia	13.0 nM [Ki]
Dopamine D2 receptor 276	Antagonist 2491	Schizophrenia	2.8 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 301	Primary	Serotonin 7 (5-HT7) receptor Dopamine D3 receptor Serotonin 2b (5-HT2b) receptor Dopamine D2 receptor	Approved 7883	SOLIAN
Psychotic symptoms 2			Approved (off-label) 8

PubMed

Title	Date	PubMed
Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor.	1992 Apr 10	1354163
Amisulpride: is there a treatment for negative symptoms in schizophrenia patients?	2002	12693427
A double-blind, randomised comparative trial of amisulpride versus olanzapine in the treatment of schizophrenia: short-term results at two months.	2002	12442883
Switching to amisulpride.	2002	12418609
Long-term effects of the substituted benzamide derivative amisulpride on baseline and stimulated prolactin levels.	2002	12207145
Switching antipsychotic medications: general recommendations and switching to amisulpride.	2002	12201620
SPECT imaging, clinical features, and cognition before and after low doses of amisulpride in schizophrenic patients with the deficit syndrome.	2002 Aug 20	12165366
Dopaminergic deficit and the role of amisulpride in the treatment of schizophrenia.	2002 Dec	12685918
Liver function tests during treatment with antipsychotic drugs: a case series of 23 patients.	2002 Dec	12502031
Dose-related effects of amisulpride on five dimensions of psychopathology in patients with acute exacerbation of schizophrenia.	2002 Dec	12454554
Gateways to clinical trials.	2002 Jan-Feb	11980386
Effect of the amisulpride isomers on rat prolactinemia.	2002 Jul 19	12144950
Variations in prescribing atypical antipsychotic drugs in primary care: cross-sectional study.	2002 Jun	12138596
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	12107616
Carmoxirole is able to reduce amisulpride-induced hyperprolactinemia without affecting its central effect.	2002 Jun 28	12106810
Neuroleptic malignant syndrome due to atypical neuroleptics: three episodes in one patient.	2002 May	12107858
Switching to amisulpride due to hepatic complications.	2002 May	12052579
Tardive dyskinesias and antipsychotics: a review.	2002 May	12052573
Effect of the amisulpride isomers on rat catalepsy.	2002 May 24	12191584
Amisulpride does not prevent relapse in primary alcohol dependence: results of a pilot randomized, placebo-controlled trial.	2002 Oct	12394288
A comparison of paroxetine versus paroxetine plus amisulpride in the treatment of dysthymic disorder: efficacy and psychosocial outcomes.	2002 Oct 10	12429360
New generation antipsychotics for first episode schizophrenia.	2003	14584012
Benefits and risks of pharmacotherapy for dysthymia: a systematic appraisal of the evidence.	2003	12495364
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	12900302
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	12888196
Which neuroleptic would psychiatrists take for themselves or their relatives?	2003 Feb	12648897
Amisulpride versus risperidone in the treatment of schizophrenic patients: a double-blind pilot study in Taiwan.	2003 Jan	12684609
Lack of effect of amisulpride on the pharmacokinetics and safety of lithium.	2003 Jun	12890302
Rapid high-performance liquid chromatographic measurement of amisulpride in human plasma: application to manage acute intoxication.	2003 Jun 5	12726848
The new and evolving pharmacotherapy of schizophrenia.	2003 Mar	12683264
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	12644990
[Plasma prolactin level and incidence of adverse endocrinologic effects during therapy with atypical neuroleptics].	2003 May	14509051
New generation antipsychotics versus low-potency conventional antipsychotics: a systematic review and meta-analysis.	2003 May 10	12747876
How does the benzamide antipsychotic amisulpride get into the brain?--An in vitro approach comparing amisulpride with clozapine.	2003 Nov	12865899
Metabolic drug interactions with new psychotropic agents.	2003 Oct	14703714
Amisulpride: limbic specificity and the mechanism of antipsychotic atypicality.	2003 Oct	14642970
The antinociceptive effect of amisulpride in mice is mediated through opioid mechanisms.	2003 Oct 8	14575800
Response of catatonic schizophrenia to amisulpride: a case report.	2003 Sep	14574833
Adverse metabolic effects associated with atypical antipsychotics: literature review and clinical implications.	2004	15025545
Amisulpride is an "atypical" antipsychotic associated with low weight gain.	2004 Apr	14647963
Combination of amisulpride and olanzapine in treatment-resistant schizophrenic psychoses.	2004 Feb	14969782
Combination of clozapine and amisulpride in treatment-resistant schizophrenia--case reports and review of the literature.	2004 Jan	14750045
Evidence-based pharmacotherapy of schizophrenia.	2004 Jun	15043765
Dopaminergic receptors in rat dura mater: pharmacological characteristics.	2004 Mar	15008964
Dosage finding and outcome in the treatment of schizophrenic inpatients with amisulpride. Results of a drug utilization observation study.	2004 Mar	14994321
Lower risk for tardive dyskinesia associated with second-generation antipsychotics: a systematic review of 1-year studies.	2004 Mar	14992963
How do we choose between atypical antipsychotics? The advantages of amisulpride.	2004 Mar	14972081
Amisulpride a selective dopamine antagonist and atypical antipsychotic: results of a meta-analysis of randomized controlled trials.	2004 Mar	14972080
Successful treatment of Tourette's disorder with amisulpride.	2004 May	15010520
Prolactinemia is uncoupled from central D2/D3 dopamine receptor occupancy in amisulpride treated patients.	2004 Sep	14997280

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

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Name

Type

Language

AMISULPRIDE

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