(S)-(-)-sulpiride (CHEBI:64119)

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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

Average Mass

341.42600

Monoisotopic Mass

341.14093

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
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

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 )

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

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

Last Modified

22 February 2017