CHEBI:64119 - (S)-(−)-sulpiride

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ChEBI Name (S)-(−)-sulpiride
ChEBI ID CHEBI:64119
ChEBI ASCII Name (S)-(-)-sulpiride
Definition An optically active form of sulpiride having (S)-configuration. The active enantiomer of the racemic drug sulpiride. Selective D2-like dopamine antagonist (Ki values are ~ 0.015. ~ 0.013, 1, ~ 45 and ~ 77 μM at D2, D3, D4, D1 and D5 receptors respectively).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H23N3O4S
Net Charge 0
Average Mass 341.42600
Monoisotopic Mass 341.141
InChI InChI=1S/C15H23N3O4S/c1-3-18-8-4-5-11(18)10-17-15(19)13-9-12(23(16,20)21)6-7-14(13)22-2/h6-7,9,11H,3-5,8,10H2,1-2H3,(H,17,19)(H2,16,20,21)/t11-/m0/s1
InChIKey BGRJTUBHPOOWDU-NSHDSACASA-N
SMILES CCN1CCC[C@H]1CNC(=O)c1cc(ccc1OC)S(N)(=O)=O
Roles Classification
Biological Role(s): dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
(via sulpiride )
Application(s): dopaminergic antagonist
A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
(via sulpiride )
antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
(via sulpiride )
antiemetic
A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.
(via sulpiride )
antipsychotic agent
Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
(via sulpiride )
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ChEBI Ontology
Outgoing (S)-(−)-sulpiride (CHEBI:64119) has role antidepressant (CHEBI:35469)
(S)-(−)-sulpiride (CHEBI:64119) has role antiemetic (CHEBI:50919)
(S)-(−)-sulpiride (CHEBI:64119) has role antipsychotic agent (CHEBI:35476)
(S)-(−)-sulpiride (CHEBI:64119) has role dopaminergic antagonist (CHEBI:48561)
(S)-(−)-sulpiride (CHEBI:64119) is a sulpiride (CHEBI:32168)
(S)-(−)-sulpiride (CHEBI:64119) is enantiomer of (R)-(+)-sulpiride (CHEBI:64122)
Incoming (R)-(+)-sulpiride (CHEBI:64122) is enantiomer of (S)-(−)-sulpiride (CHEBI:64119)
IUPAC Name
N-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2-methoxy-5-sulfamoylbenzamide
INNs Sources
levosulpirida DrugBank
levosulpiride KEGG DRUG
levosulpiridum DrugBank
Synonyms Sources
(−)-sulpiride ChEBI
(-)-N-(((S)-1-Ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-o-anisamide ChemIDplus
(S)-(−)-5-aminosulfonyl-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide ChEBI
(S)-(-)-N-((1-Ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-o-anisamide ChemIDplus
(S)-sulpiride ChEBI
S-(-)-N-(1-Ethyl-2-pyrrolidinomethyl)-2-methoxy-5-sulfamoylebenzamide ChemIDplus
Database Links Databases
1577 DrugCentral
D07312 KEGG DRUG
DB00391 DrugBank
KR20110090142 Patent
Levosulpiride Wikipedia
LSM-5624 LINCS
US2011052700 Patent
View more database links
Registry Numbers Types Sources
23672-07-3 CAS Registry Number ChemIDplus
3563418 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18186115 PubMed citation Europe PMC
19165957 PubMed citation Europe PMC
19452563 PubMed citation Europe PMC
19488984 PubMed citation Europe PMC
19795476 PubMed citation Europe PMC
20438811 PubMed citation Europe PMC
20656570 PubMed citation Europe PMC
20850200 PubMed citation Europe PMC
21223496 PubMed citation Europe PMC
21615988 PubMed citation Europe PMC
Last Modified
22 February 2017