CHEBI:64045 - amisulpride

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ChEBI Name amisulpride
ChEBI ID CHEBI:64045
Definition A member of the class of benzamides resulting from the formal condensation of the carboxy group of 4-amino-5-(ethylsulfonyl)-2-methoxybenzoic acid with the primary amino group of 2-(aminomethyl)-1-ethylpyrrolidine. It is a potent, selective dopamine D2 and D3 receptor antagonist. It is an atypical antipsychotic/antischizophrenic agent with limited extrapyrimidal side effects.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C17H27N3O4S
Net Charge 0
Average Mass 369.47900
Monoisotopic Mass 369.172
InChI 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)
InChIKey NTJOBXMMWNYJFB-UHFFFAOYSA-N
SMILES CCN1CCCC1CNC(=O)c1cc(c(N)cc1OC)S(=O)(=O)CC
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): second generation antipsychotic
Antipsychotic drugs which can have different modes of action but which tend to be less likely than first generation antipsychotics to cause extrapyramidal motor control disabilities such as body rigidity or Parkinson's disease-type movements.
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ChEBI Ontology
Outgoing amisulpride (CHEBI:64045) has role environmental contaminant (CHEBI:78298)
amisulpride (CHEBI:64045) has role second generation antipsychotic (CHEBI:65191)
amisulpride (CHEBI:64045) has role xenobiotic (CHEBI:35703)
amisulpride (CHEBI:64045) is a aromatic amide (CHEBI:62733)
amisulpride (CHEBI:64045) is a aromatic amine (CHEBI:33860)
amisulpride (CHEBI:64045) is a benzamides (CHEBI:22702)
amisulpride (CHEBI:64045) is a pyrrolidines (CHEBI:38260)
amisulpride (CHEBI:64045) is a sulfone (CHEBI:35850)
IUPAC Name
4-amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide
INNs Sources
amisulprida ChemIDplus
amisulpride KEGG DRUG
amisulpridum ChemIDplus
Synonyms Sources
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide ChemIDplus
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-o-anisamide ChemIDplus
Aminosultopride DrugBank
Manual Xrefs Databases
179 DrugCentral
Amisulpride Wikipedia
BE872585 Patent
D07310 KEGG DRUG
DB06288 DrugBank
HMDB0015633 HMDB
LSM-1669 LINCS
US4401822 Patent
View more database links
Registry Numbers Types Sources
6876191 Reaxys Registry Number Reaxys
71675-85-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
21176108 PubMed citation Europe PMC
21647545 PubMed citation Europe PMC
21663752 PubMed citation Europe PMC
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21969105 PubMed citation Europe PMC
22035899 PubMed citation Europe PMC
22059694 PubMed citation Europe PMC
22121864 PubMed citation Europe PMC
22241281 PubMed citation Europe PMC
22250612 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag