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

Molecular Formula C17H27N3O4S
Molecular Weight 369.4807
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
(-)S amisulpride binds with high affinity to cloned dopamine D(3) and D(2) receptors.
2001 Dec 7
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 implications of dopamine research in schizophrenia.
2002
Spotlight on amisulpride in 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
Amisulpride improves depressive symptoms in acute exacerbations of schizophrenia: comparison with haloperidol and risperidone.
2002 Aug
Dose-related effects of amisulpride on five dimensions of psychopathology in patients with acute exacerbation of schizophrenia.
2002 Dec
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
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
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
Which neuroleptic would psychiatrists take for themselves or their relatives?
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
A meta-analysis of the efficacy of second-generation antipsychotics.
2003 Jun
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
Evidence-based pharmacotherapy of schizophrenia.
2004 Jun
Dopaminergic receptors in rat dura mater: pharmacological characteristics.
2004 Mar
Lower risk for tardive dyskinesia associated with second-generation antipsychotics: a systematic review of 1-year studies.
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
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 Fri Jun 25 21:12:55 UTC 2021
Edited
by admin
on Fri Jun 25 21:12:55 UTC 2021
Record UNII
8110R61I4U
Record Status Validated (UNII)
Record Version
  • Download
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
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

IN HEALTHY SUBJECTS

Volume of Distribution PHARMACOKINETIC IN SURGICAL PATIENTS

FOLLOWING INTRAVENOUS INFUSION

Biological Half-life PHARMACOKINETIC IN HEALTHY SUBJECTS AND SURGICAL PATIENTS

FOLLOWING INTRAVENOUS INFUSION