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
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)
DescriptionSources: http://www.sanofi.com.au/products/aus_pi_solian.pdfCurator'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
Sources: http://www.sanofi.com.au/products/aus_pi_solian.pdf
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL217 |
2.8 nM [Ki] | ||
Target ID: CHEMBL234 |
3.2 nM [Ki] | ||
Target ID: CHEMBL3155 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19337725 |
11.5 nM [Ki] | ||
Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19337725 |
13.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | SOLIAN Approved UseAmisulpride 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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
586.3 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28793958 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5043.2 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28793958 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse events |
---|---|---|
6 g single, oral Overdose |
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%) Sources: Dystonic reaction (2 patients) |
6 g single, oral Overdose |
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%) Sources: Tachycardia (23%) |
80 g single, oral Overdose |
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... |
20 mg single, intravenous Highest studied dose Dose: 20 mg Route: intravenous Route: single Dose: 20 mg Sources: |
unhealthy n = 18 |
|
200 mg single, oral Highest studied dose |
healthy n = 20 |
|
1200 mg single, oral Overdose Dose: 1200 mg Route: oral Route: single Dose: 1200 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Extrapyramidal disorder... Other AEs: Extrapyramidal disorder Sources: |
3000 mg single, oral Overdose |
unhealthy n = 1 |
Other AEs: Hyperthermia, Mydriasis... Other AEs: Hyperthermia (1 patient) Sources: Mydriasis (1 patient) Coma (1 patient) Seizures (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Dystonic reaction | 2 patients | 6 g single, oral Overdose |
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 |
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 |
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 |
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 |
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 Health Status: unhealthy Sources: |
|
Coma | 1 patient | 3000 mg single, oral Overdose |
unhealthy n = 1 |
Hyperthermia | 1 patient | 3000 mg single, oral Overdose |
unhealthy n = 1 |
Mydriasis | 1 patient | 3000 mg single, oral Overdose |
unhealthy n = 1 |
Seizures | 1 patient | 3000 mg single, oral Overdose |
unhealthy n = 1 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 46.1 uM] | ||||
no [IC50 >100 uM] | ||||
no [IC50 >100 uM] | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/209510Orig1s000MultidisciplineR.pdf#page=179 Page: 179.0 |
no | |||
no | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/209510Orig1s000MultidisciplineR.pdf#page=179 Page: 179.0 |
no | |||
no | ||||
no | ||||
no | ||||
no | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/209510Orig1s000MultidisciplineR.pdf#page=179 Page: 179.0 |
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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
weak | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor. | 1992 Apr 10 |
|
Amisulpride: a review of its use in the management of schizophrenia. | 2001 |
|
[Initial experiences with amisulpride, an in Germany novel, atypical neuroleptic drug in treatment of adolescents with psychiatric disorders]. | 2001 Aug |
|
Effects of newer atypical antipsychotics on autonomic neurocardiac function: a comparison between amisulpride, olanzapine, sertindole, and clozapine. | 2001 Feb |
|
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 |
|
Clinical implications of dopamine research in schizophrenia. | 2002 |
|
Switching antipsychotic medications: general recommendations and switching to amisulpride. | 2002 |
|
Amisulpride improves depressive symptoms in acute exacerbations of schizophrenia: comparison with haloperidol and risperidone. | 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 |
|
Dopaminergic deficit and the role of amisulpride in the treatment of schizophrenia. | 2002 Dec |
|
Liver function tests during treatment with antipsychotic drugs: a case series of 23 patients. | 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 |
|
A review of the pharmacokinetics, tolerability and pharmacodynamics of amisulpride in healthy volunteers. | 2002 Jan |
|
Social functioning and quality of life in the schizophrenic patient: advantages of amisulpride. | 2002 Jan |
|
Efficacy and safety of amisulpride 50 mg versus paroxetine 20 mg in major depression: a randomized, double-blind, parallel group study. | 2002 Jan |
|
The glial growth factors deficiency and synaptic destabilization hypothesis of schizophrenia. | 2002 Jul 3 |
|
[Use of atypical antipsychotics in Charles Perrens psychiatric hospital (Bordeaux) analysis of prescribing practices for Amisulpride, Clozapine, Olanzapine and Risperidone]. | 2002 Jul-Aug |
|
Variations in prescribing atypical antipsychotic drugs in primary care: cross-sectional study. | 2002 Jun |
|
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 |
|
Effect of the amisulpride isomers on rat catalepsy. | 2002 May 24 |
|
Discriminative stimulus properties in rats of the novel antipsychotic quetiapine. | 2002 Nov |
|
A comparison of paroxetine versus paroxetine plus amisulpride in the treatment of dysthymic disorder: efficacy and psychosocial outcomes. | 2002 Oct 10 |
|
New generation antipsychotics for first episode schizophrenia. | 2003 |
|
Respective roles of dopamine D2 and D3 receptors in food-seeking behaviour in rats. | 2003 Feb |
|
Automated determination of amisulpride by liquid chromatography with column switching and spectrophotometric detection. | 2003 Feb 5 |
|
[Frontal dysfunctions in Huntington's disease -- neuropsychology and therapy]. | 2003 Jan |
|
Quantification of D2-like dopamine receptors in the human brain with 18F-desmethoxyfallypride. | 2003 Jan |
|
Adverse metabolic effects associated with atypical antipsychotics: literature review and clinical implications. | 2004 |
|
Evidence-based pharmacotherapy of schizophrenia. | 2004 Jun |
|
Dopaminergic receptors in rat dura mater: pharmacological characteristics. | 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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8996185
In NG108-15 cells stably transfected with the human D3 dopamine receptor amisulpride inhibited quinpirole-elicited mitogenesis with an IC50 value of 22 nM
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C66883
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WHO-VATC |
QN05AL05
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WHO-ATC |
N05AL05
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SUB05458MIG
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8110R61I4U
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4960
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FG-201
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C83533
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64045
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AMISULPRIDE
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DB06288
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CHEMBL243712
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m1751
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71675-85-9
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8110R61I4U
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275-831-7
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100000087234
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179
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963
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2159
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46303
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Amisulpride
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ACTIVE MOIETY