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 |
---|---|---|
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 |
|
Extrastriatal and striatal D(2) dopamine receptor blockade with haloperidol or new antipsychotic drugs in patients with schizophrenia. | 2001 Dec |
|
(-)S amisulpride binds with high affinity to cloned dopamine D(3) and D(2) receptors. | 2001 Dec 7 |
|
Asymptomatic bradycardia associated with amisulpride. | 2001 Nov |
|
Faster response on amisulpride 50 mg versus sertraline 50-100 mg in patients with dysthymia or double depression: a randomized, double-blind, parallel group study. | 2001 Nov |
|
Clinical advantages of amisulpride in the treatment of acute schizophrenia. | 2001 Nov-Dec |
|
Long-term effects of the substituted benzamide derivative amisulpride on baseline and stimulated prolactin levels. | 2002 |
|
Focus on amisulpride. | 2002 |
|
Effects of newer antipsychotics on extrapyramidal function. | 2002 |
|
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 |
|
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 |
|
Striatal dopamine-2 receptor occupancy as measured with [123I]iodobenzamide and SPECT predicted the occurrence of EPS in patients treated with atypical antipsychotics and haloperidol. | 2002 Jun |
|
Carmoxirole is able to reduce amisulpride-induced hyperprolactinemia without affecting its central effect. | 2002 Jun 28 |
|
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 |
|
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 |
|
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 |
|
Automated determination of amisulpride by liquid chromatography with column switching and spectrophotometric detection. | 2003 Feb 5 |
|
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 |
|
Quetiapine. A review of its use in the management of schizophrenia. | 2004 |
|
Combination of amisulpride and olanzapine in treatment-resistant schizophrenic psychoses. | 2004 Feb |
|
Amisulpride a selective dopamine antagonist and atypical antipsychotic: results of a meta-analysis of randomized controlled trials. | 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
Sat Dec 16 17:29:20 GMT 2023
by
admin
on
Sat Dec 16 17:29:20 GMT 2023
|
Record UNII |
8110R61I4U
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C66883
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
||
|
WHO-VATC |
QN05AL05
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
||
|
WHO-ATC |
N05AL05
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
SUB05458MIG
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
8110R61I4U
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
4960
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
FG-201
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
C83533
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
64045
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
AMISULPRIDE
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
DB06288
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
CHEMBL243712
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
m1751
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | Merck Index | ||
|
71675-85-9
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
8110R61I4U
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
275-831-7
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
100000087234
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
179
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
963
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
2159
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
46303
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | RxNorm | ||
|
Amisulpride
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
DTXSID5042613
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY | |||
|
760085
Created by
admin on Sat Dec 16 17:29:22 GMT 2023 , Edited by admin on Sat Dec 16 17:29:22 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ENANTIOMER -> RACEMATE | |||
|
TARGET->ANTAGONIST |
SELECTIVE
|
||
|
TRANSPORTER -> INHIBITOR | |||
|
TRANSPORTER -> SUBSTRATE | |||
|
TRANSPORTER -> SUBSTRATE | |||
|
TARGET->ANTAGONIST |
ANTAGONIST
Ki
|
||
|
TRANSPORTER -> INHIBITOR | |||
|
EXCRETED UNCHANGED |
AMOUNT EXCRETED
URINE
|
||
|
ENANTIOMER -> RACEMATE | |||
|
BINDER->LIGAND |
Plasma protein binding is 25% to 30% in the concentration range from 37 to 1850 ng/mL.
BINDING
|
||
|
EXCRETED UNCHANGED |
AMOUNT EXCRETED
FECAL
|
||
|
TRANSPORTER -> SUBSTRATE | |||
|
METABOLIC ENZYME -> SUBSTRATE | |||
|
METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Volume of Distribution | PHARMACOKINETIC |
|
FOLLOWING INTRAVENOUS INFUSION |
|
||
Volume of Distribution | PHARMACOKINETIC |
|
IN SURGICAL PATIENTS |
|
||
Biological Half-life | PHARMACOKINETIC |
|
IN HEALTHY SUBJECTS AND SURGICAL PATIENTS |
|
||