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)
Molecular Formula | C17H27N3O4S |
Molecular Weight | 369.479 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 |
---|---|---|
In vivo extrastriatal and striatal D2 dopamine receptor blockade by amisulpride in schizophrenia. | 2001 Apr |
|
Extrastriatal and striatal D(2) dopamine receptor blockade with haloperidol or new antipsychotic drugs in patients with schizophrenia. | 2001 Dec |
|
Amisulpride: progress and outcomes. | 2002 |
|
Spotlight on amisulpride in schizophrenia. | 2002 |
|
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 |
|
Atypical antipsychotics: mechanism of action. | 2002 Feb |
|
Amisulpride, an unusual "atypical" antipsychotic: a meta-analysis of randomized controlled trials. | 2002 Feb |
|
Efficacy and safety of amisulpride 50 mg versus paroxetine 20 mg in major depression: a randomized, double-blind, parallel group study. | 2002 Jan |
|
Intolerance to neuroleptics and susceptibility for malignant hyperthermia in a patient with proximal myotonic myopathy (PROMM) and schizophrenia. | 2002 Jan |
|
Gateways to clinical trials. | 2002 Jan-Feb |
|
New antipsychotic agents for schizophrenia: pharmacokinetics and metabolism update. | 2002 Jul |
|
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 |
|
[Use of atypical antipsychotics in Charles Perrens psychiatric hospital (Bordeaux) analysis of prescribing practices for Amisulpride, Clozapine, Olanzapine and Risperidone]. | 2002 Jul-Aug |
|
Carmoxirole is able to reduce amisulpride-induced hyperprolactinemia without affecting its central effect. | 2002 Jun 28 |
|
Tardive dyskinesias and antipsychotics: a review. | 2002 May |
|
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 |
|
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 |
|
Quantification of D2-like dopamine receptors in the human brain with 18F-desmethoxyfallypride. | 2003 Jan |
|
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 |
|
[Plasma prolactin level and incidence of adverse endocrinologic effects during therapy with atypical neuroleptics]. | 2003 May |
|
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 |
|
Adverse metabolic effects associated with atypical antipsychotics: literature review and clinical implications. | 2004 |
|
Combination of clozapine and amisulpride in treatment-resistant schizophrenia--case reports and review of the literature. | 2004 Jan |
|
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 |
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Sun Dec 18 20:20:17 UTC 2022
by
admin
on
Sun Dec 18 20:20:17 UTC 2022
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Record UNII |
8110R61I4U
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Record Status |
Validated (UNII)
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Record Version |
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-
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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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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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DTXSID5042613
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760085
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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TARGET->ANTAGONIST |
SELECTIVE
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE | |||
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TARGET->ANTAGONIST |
ANTAGONIST
Ki
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TRANSPORTER -> INHIBITOR | |||
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
URINE
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ENANTIOMER -> RACEMATE | |||
|
BINDER->LIGAND |
Plasma protein binding is 25% to 30% in the concentration range from 37 to 1850 ng/mL.
BINDING
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
FECAL
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TRANSPORTER -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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FOLLOWING INTRAVENOUS INFUSION |
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Volume of Distribution | PHARMACOKINETIC |
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IN SURGICAL PATIENTS |
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Biological Half-life | PHARMACOKINETIC |
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IN HEALTHY SUBJECTS AND SURGICAL PATIENTS |
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