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=C(OC)C=C(N)C(=C2)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
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8996185 | https://www.ncbi.nlm.nih.gov/pubmed/19337725 | https://www.ncbi.nlm.nih.gov/pubmed/11735643

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SOLIAN

Approved Use

Amisulpride is indicated for the treatment of acute and chronic schizophrenic disorders, in which positive symptoms (such as delusions, hallucinations, thought disorders) and/or negative symptoms (such as blunted affect, emotional and social withdrawal) are prominent, including patients characterised by predominant negative symptoms.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
586.3 ng/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMISULPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
5043.2 ng × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMISULPRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11.7 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMISULPRIDE unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
6 g single, oral
Overdose
Dose: 6 g
Route: oral
Route: single
Dose: 6 g
Sources:
unhealthy, 29 years (range: 23-40 years)
n = 23
Health Status: unhealthy
Age Group: 29 years (range: 23-40 years)
Sex: M+F
Population Size: 23
Sources:
Other AEs: Bradycardia, Dystonic reaction...
Other AEs:
Bradycardia (24%)
Dystonic reaction (2 patients)
Sources:
6 g single, oral
Overdose
Dose: 6 g
Route: oral
Route: single
Dose: 6 g
Sources:
unhealthy, 29 years (range: 23-40 years)
n = 49
Health Status: unhealthy
Age Group: 29 years (range: 23-40 years)
Sex: M+F
Population Size: 49
Sources:
Other AEs: QT interval prolonged, Tachycardia...
Other AEs:
QT interval prolonged (64%)
Tachycardia (23%)
Sources:
80 g single, oral
Overdose
Dose: 80 g
Route: oral
Route: single
Dose: 80 g
Sources:
unhealthy, 29 years (range: 23-40 years)
n = 49
Health Status: unhealthy
Age Group: 29 years (range: 23-40 years)
Sex: M+F
Population Size: 49
Sources:
Other AEs: Torsades de pointes...
Other AEs:
Torsades de pointes (7%)
Sources:
20 mg single, intravenous
Highest studied dose
Dose: 20 mg
Route: intravenous
Route: single
Dose: 20 mg
Sources:
unhealthy
n = 18
Health Status: unhealthy
Population Size: 18
Sources:
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
healthy
n = 20
Health Status: healthy
Sex: M+F
Population Size: 20
Sources:
1200 mg single, oral
Overdose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
unhealthy
Other AEs: Extrapyramidal disorder...
3000 mg single, oral
Overdose
Dose: 3000 mg
Route: oral
Route: single
Dose: 3000 mg
Sources:
unhealthy
n = 1
Health Status: unhealthy
Population Size: 1
Sources:
Other AEs: Hyperthermia, Mydriasis...
Other AEs:
Hyperthermia (1 patient)
Mydriasis (1 patient)
Coma (1 patient)
Seizures (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Dystonic reaction 2 patients
6 g single, oral
Overdose
Dose: 6 g
Route: oral
Route: single
Dose: 6 g
Sources:
unhealthy, 29 years (range: 23-40 years)
n = 23
Health Status: unhealthy
Age Group: 29 years (range: 23-40 years)
Sex: M+F
Population Size: 23
Sources:
Bradycardia 24%
6 g single, oral
Overdose
Dose: 6 g
Route: oral
Route: single
Dose: 6 g
Sources:
unhealthy, 29 years (range: 23-40 years)
n = 23
Health Status: unhealthy
Age Group: 29 years (range: 23-40 years)
Sex: M+F
Population Size: 23
Sources:
Tachycardia 23%
6 g single, oral
Overdose
Dose: 6 g
Route: oral
Route: single
Dose: 6 g
Sources:
unhealthy, 29 years (range: 23-40 years)
n = 49
Health Status: unhealthy
Age Group: 29 years (range: 23-40 years)
Sex: M+F
Population Size: 49
Sources:
QT interval prolonged 64%
6 g single, oral
Overdose
Dose: 6 g
Route: oral
Route: single
Dose: 6 g
Sources:
unhealthy, 29 years (range: 23-40 years)
n = 49
Health Status: unhealthy
Age Group: 29 years (range: 23-40 years)
Sex: M+F
Population Size: 49
Sources:
Torsades de pointes 7%
80 g single, oral
Overdose
Dose: 80 g
Route: oral
Route: single
Dose: 80 g
Sources:
unhealthy, 29 years (range: 23-40 years)
n = 49
Health Status: unhealthy
Age Group: 29 years (range: 23-40 years)
Sex: M+F
Population Size: 49
Sources:
Extrapyramidal disorder
1200 mg single, oral
Overdose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
unhealthy
Coma 1 patient
3000 mg single, oral
Overdose
Dose: 3000 mg
Route: oral
Route: single
Dose: 3000 mg
Sources:
unhealthy
n = 1
Health Status: unhealthy
Population Size: 1
Sources:
Hyperthermia 1 patient
3000 mg single, oral
Overdose
Dose: 3000 mg
Route: oral
Route: single
Dose: 3000 mg
Sources:
unhealthy
n = 1
Health Status: unhealthy
Population Size: 1
Sources:
Mydriasis 1 patient
3000 mg single, oral
Overdose
Dose: 3000 mg
Route: oral
Route: single
Dose: 3000 mg
Sources:
unhealthy
n = 1
Health Status: unhealthy
Population Size: 1
Sources:
Seizures 1 patient
3000 mg single, oral
Overdose
Dose: 3000 mg
Route: oral
Route: single
Dose: 3000 mg
Sources:
unhealthy
n = 1
Health Status: unhealthy
Population Size: 1
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 46.1 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no
no
no
no
no
no
no
no
no
no
no
no
weak [Inhibition 100 uM]
weak [Inhibition 100 uM]
yes [IC50 10.1 uM]
yes [IC50 16.1 uM]
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
weak
yes
yes
yes
Tox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor.
1992 Apr 10
Asymptomatic bradycardia associated with amisulpride.
2001 Nov
Clinical advantages of amisulpride in the treatment of acute schizophrenia.
2001 Nov-Dec
Switching to amisulpride.
2002
Clinical implications of dopamine research in schizophrenia.
2002
Switching antipsychotic medications: general recommendations and switching to amisulpride.
2002
Focus on amisulpride.
2002
Perazine for schizophrenia.
2002
Effects of newer antipsychotics on extrapyramidal function.
2002
Review: amisulpride is effective and safe for schizophrenia.
2002 Aug
Amisulpride improves depressive symptoms in acute exacerbations of schizophrenia: comparison with haloperidol and risperidone.
2002 Aug
Liver function tests during treatment with antipsychotic drugs: a case series of 23 patients.
2002 Dec
Effects of amisulpride on consummatory negative contrast.
2002 Dec
Atypical antipsychotics: mechanism of action.
2002 Feb
Social functioning and quality of life in the schizophrenic patient: advantages of amisulpride.
2002 Jan
Gateways to clinical trials.
2002 Jan-Feb
New antipsychotic agents for schizophrenia: pharmacokinetics and metabolism update.
2002 Jul
[Use of atypical antipsychotics in Charles Perrens psychiatric hospital (Bordeaux) analysis of prescribing practices for Amisulpride, Clozapine, Olanzapine and Risperidone].
2002 Jul-Aug
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
Switching to amisulpride due to hepatic complications.
2002 May
Effect of the amisulpride isomers on rat catalepsy.
2002 May 24
Discriminative stimulus properties in rats of the novel antipsychotic quetiapine.
2002 Nov
Amisulpride does not prevent relapse in primary alcohol dependence: results of a pilot randomized, placebo-controlled trial.
2002 Oct
Differential effects of high-dose amisulpride versus flupentixol on latent dimensions of depressive and negative symptomatology in acute schizophrenia: an evaluation using confirmatory factor analysis.
2002 Sep
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
[Frontal dysfunctions in Huntington's disease -- neuropsychology and therapy].
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
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
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
Quetiapine. A review of its use in the management of schizophrenia.
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
Characterization of the effects of receptor-selective ligands in rats discriminating the novel antipsychotic quetiapine.
2004 Jan
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
Prolactinemia is uncoupled from central D2/D3 dopamine receptor occupancy in amisulpride treated patients.
2004 Sep
Patents

Sample Use Guides

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
Amisulpride [WHO-DD]
Common Name English
APD421
Code English
BARHEMSYS
Brand Name English
BENZAMIDE, 4-AMINO-N-((1-ETHYL-2-PYRROLIDINYL)METHYL)-5-(ETHYLSULFONYL)-2-METHOXY-
Systematic Name English
SULAMID
Brand Name English
DAN-2163
Code English
AMISULPRIDE [MI]
Common Name English
APD-421
Code English
SOLIAN
Brand Name English
NSC-760085
Code English
DENIBAN
Brand Name English
(±)-AMISULPRIDE
Common Name English
AMISULPRIDE [EP MONOGRAPH]
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 [ORANGE BOOK]
Common Name English
amisulpride [INN]
Common Name English
AMINOSULTOPRIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66883
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
WHO-VATC QN05AL05
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
WHO-ATC N05AL05
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
Code System Code Type Description
EVMPD
SUB05458MIG
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
DAILYMED
8110R61I4U
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
INN
4960
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
USAN
FG-201
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
NCI_THESAURUS
C83533
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
CHEBI
64045
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
WIKIPEDIA
AMISULPRIDE
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
DRUG BANK
DB06288
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL243712
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PRIMARY
MERCK INDEX
m1751
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY Merck Index
CAS
71675-85-9
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
FDA UNII
8110R61I4U
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
ECHA (EC/EINECS)
275-831-7
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PRIMARY
SMS_ID
100000087234
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
DRUG CENTRAL
179
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
IUPHAR
963
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
PUBCHEM
2159
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
RXCUI
46303
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY RxNorm
LACTMED
Amisulpride
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID5042613
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY
NSC
760085
Created by admin on Sat Dec 16 17:29:22 UTC 2023 , Edited by admin on Sat Dec 16 17:29:22 UTC 2023
PRIMARY