U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C17H27N3O4S
Molecular Weight 369.4807
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMISULPRIDE

SMILES

CCN1CCCC1CN=C(c2cc(c(cc2OC)N)S(=O)(=O)CC)O

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
Amisulpride: a review of its use in the management of schizophrenia.
2001
In vivo extrastriatal and striatal D2 dopamine receptor blockade by amisulpride in schizophrenia.
2001 Apr
[Initial experiences with amisulpride, an in Germany novel, atypical neuroleptic drug in treatment of adolescents with psychiatric disorders].
2001 Aug
Amisulpride: efficacy in the management of chronic patients with predominant negative symptoms of schizophrenia.
2001 Oct
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
Amisulpride: progress and outcomes.
2002
Clinical implications of dopamine research in schizophrenia.
2002
Long-term effects of the substituted benzamide derivative amisulpride on baseline and stimulated prolactin levels.
2002
Spotlight on amisulpride in schizophrenia.
2002
Perazine for schizophrenia.
2002
Sub-chronic treatment with classical but not atypical antipsychotics produces morphological changes in rat nigro-striatal dopaminergic neurons directly related to "early onset" vacuous chewing.
2002 Apr
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
Dopaminergic deficit and the role of amisulpride in the treatment of mood disorders.
2002 Dec
Amisulpride vs. risperidone in chronic schizophrenia: results of a 6-month double-blind study.
2002 Dec
Dose-related effects of amisulpride on five dimensions of psychopathology in patients with acute exacerbation of schizophrenia.
2002 Dec
Atypical antipsychotics: mechanism of action.
2002 Feb
A review of the pharmacokinetics, tolerability and pharmacodynamics of amisulpride in healthy volunteers.
2002 Jan
Comparative efficacy of SSRIs and amisulpride in burning mouth syndrome: a single-blind study.
2002 Jan
Gateways to clinical trials.
2002 Jan-Feb
Effect of the amisulpride isomers on rat prolactinemia.
2002 Jul 19
The glial growth factors deficiency and synaptic destabilization hypothesis of schizophrenia.
2002 Jul 3
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
Effect of the amisulpride isomers on rat catalepsy.
2002 May 24
Age-related changes in dopamine D2 receptors in rat heart and coronary vessels.
2002 May-Jun
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
Which neuroleptic would psychiatrists take for themselves or their relatives?
2003 Feb
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
Lack of effect of amisulpride on the pharmacokinetics and safety of lithium.
2003 Jun
A meta-analysis of the efficacy of second-generation antipsychotics.
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
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
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
Lower risk for tardive dyskinesia associated with second-generation antipsychotics: a systematic review of 1-year studies.
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

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
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
AMISULPRIDE [WHO-DD]
Common 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 [INN]
Common Name English
AMINOSULTOPRIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66883
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
WHO-VATC QN05AL05
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
WHO-ATC N05AL05
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
Code System Code Type Description
EVMPD
SUB05458MIG
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY
INN
4960
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY
NCI_THESAURUS
C83533
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY
WIKIPEDIA
AMISULPRIDE
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY
DRUG BANK
DB06288
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY
ChEMBL
CHEMBL243712
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY
MERCK INDEX
M1751
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY Merck Index
CAS
71675-85-9
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY
FDA UNII
8110R61I4U
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY
ECHA (EC/EINECS)
275-831-7
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY
DRUG CENTRAL
179
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY
IUPHAR
963
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY
PUBCHEM
2159
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY
RXCUI
46303
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY RxNorm
LACTMED
Amisulpride
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY
EPA CompTox
71675-85-9
Created by admin on Fri Jun 25 21:12:55 UTC 2021 , Edited by admin on Fri Jun 25 21:12:55 UTC 2021
PRIMARY