CHEBI:64119 - (S)-(−)-sulpiride

ChEBI IDCHEBI:64119
ChEBI Name(S)-(−)-sulpiride
Stars
ASCII Name(S)-(-)-sulpiride
DefinitionAn 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).
Last Modified22 February 2017
SubmitterSteve
DownloadsMolfile
FormulaC15H23N3O4S
Net Charge0
Average Mass341.433
Monoisotopic Mass341.14093
SMILESCCN1CCC[C@H]1CNC(=O)c1cc(S(N)(=O)=O)ccc1OC
InChIInChI=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
InChIKeyBGRJTUBHPOOWDU-NSHDSACASA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
dopaminergic antagonist  A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
dopaminergic antagonist  A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
Applications:
antipsychotic agent  Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
dopaminergic antagonist  A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
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.
antipsychotic agent  Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
dopaminergic antagonist  A drug that binds to but does not activate dopamine receptors, thereby blocking the actions of dopamine or exogenous agonists.
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.
ChEBI Ontology
Outgoing Relation(s)
(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 Relation(s)
(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  Source
levosulpirideKEGG DRUG
levosulpiridumDrugBank
levosulpiridaDrugBank
Synonyms  Source
(−)-sulpirideChEBI
(S)-sulpirideChEBI
(-)-N-(((S)-1-Ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-o-anisamideChemIDplus
S-(-)-N-(1-Ethyl-2-pyrrolidinomethyl)-2-methoxy-5-sulfamoylebenzamideChemIDplus
(S)-(-)-N-((1-Ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-o-anisamideChemIDplus
(S)-(−)-5-aminosulfonyl-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamideChEBI
Manual XrefsDatabases
D07312KEGG DRUG
DB00391DrugBank
US2011052700Patent
KR20110090142Patent
LevosulpirideWikipedia
LSM-5624LINCS
1577DrugCentral
Registry NumbersSources
Reaxys:3563418Reaxys
CAS:23672-07-3ChemIDplus
Citations