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=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)
Molecular Formula | C17H27N3O4S |
Molecular Weight | 369.479 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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
PubMed
Title | Date | PubMed |
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Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor. | 1992 Apr 10 |
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Extrastriatal and striatal D(2) dopamine receptor blockade with haloperidol or new antipsychotic drugs in patients with schizophrenia. | 2001 Dec |
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Effects of newer atypical antipsychotics on autonomic neurocardiac function: a comparison between amisulpride, olanzapine, sertindole, and clozapine. | 2001 Feb |
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Asymptomatic bradycardia associated with amisulpride. | 2001 Nov |
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Amisulpride: efficacy in the management of chronic patients with predominant negative symptoms of schizophrenia. | 2001 Oct |
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Switching antipsychotic medications: general recommendations and switching to amisulpride. | 2002 |
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Amisulpride for schizophrenia. | 2002 |
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Spotlight on amisulpride in schizophrenia. | 2002 |
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Effects of newer antipsychotics on extrapyramidal function. | 2002 |
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A comparison of paroxetine and amisulpride in the treatment of dysthymic disorder. | 2002 Aug |
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SPECT imaging, clinical features, and cognition before and after low doses of amisulpride in schizophrenic patients with the deficit syndrome. | 2002 Aug 20 |
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Effects of amisulpride on consummatory negative contrast. | 2002 Dec |
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Atypical antipsychotics: mechanism of action. | 2002 Feb |
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A review of the pharmacokinetics, tolerability and pharmacodynamics of amisulpride in healthy volunteers. | 2002 Jan |
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New antipsychotic agents for schizophrenia: pharmacokinetics and metabolism update. | 2002 Jul |
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A systematic review of the use of atypical antipsychotics in autism. | 2002 Mar |
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[Pharmaco-epidemiological study on antipsychotic drug prescription in French Psychiatry: Patient characteristics, antipsychotic treatment, and care management for schizophrenia]. | 2002 Mar-Apr |
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Gateways to clinical trials. | 2002 May |
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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 |
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Respective roles of dopamine D2 and D3 receptors in food-seeking behaviour in rats. | 2003 Feb |
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Amisulpride versus risperidone in the treatment of schizophrenic patients: a double-blind pilot study in Taiwan. | 2003 Jan |
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Quantification of D2-like dopamine receptors in the human brain with 18F-desmethoxyfallypride. | 2003 Jan |
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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 |
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Amisulpride is an "atypical" antipsychotic associated with low weight gain. | 2004 Apr |
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Evidence-based pharmacotherapy of schizophrenia. | 2004 Jun |
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Dosage finding and outcome in the treatment of schizophrenic inpatients with amisulpride. Results of a drug utilization observation study. | 2004 Mar |
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Amisulpride a selective dopamine antagonist and atypical antipsychotic: results of a meta-analysis of randomized controlled trials. | 2004 Mar |
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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
Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Oct 22 00:18:40 UTC 2019
by
admin
on
Tue Oct 22 00:18:40 UTC 2019
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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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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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Code System | Code | Type | Description | ||
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SUB05458MIG
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4960
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C83533
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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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275-831-7
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963
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2159
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46303
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71675-85-9
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |