Levosulpiride

Levosulpiride

Names
IUPAC name N-[[(2S)-(−)-1-ethylpyrrolidin-2-yl]methyl]-2-methoxy-5-sulfamoylbenzamide
Identifiers
CAS Number	23672-07-3 Y
ChEBI	CHEBI:4119 N
ChEMBL	ChEMBL267044 N
ChemSpider	599749 N
IUPHAR/BPS	958
Jmol 3D model	Interactive image
KEGG	D07312 Y
PubChem	688272
UNII	JTG7R315LK Y
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 N Key: BGRJTUBHPOOWDU-NSHDSACASA-N N InChI=1/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 Key: BGRJTUBHPOOWDU-NSHDSACABD
SMILES CCN1CCC[C@H]1CNC(=O)C2=C(C=CC(=C2)S(=O)(=O)N)OC
Properties
Chemical formula	C15H23N3O4S
Molar mass	341.43 g·mol−1
Pharmacology
ATC code	N05AL07
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Levosulpiride is a substituted benzamide antipsychotic, reported to be a selective antagonist of dopamine D₂ receptor activity on both central and peripheral levels. It is an atypical neuroleptic and a prokinetic agent. Levosulpiride is also claimed to have mood elevating properties. Levosulpiride is used in the treatment of psychoses, particularly negative symptoms of schizophrenia, anxiety disorders, dysthymia, vertigo, dyspepsia, irritable bowel syndrome and premature ejaculation.

Chemically, it is the (S)-(−)-enantiomer of sulpiride.

Side effect

Side effects include amenorrhea, gynecomastia, galactorrhea, changes in libido, and neuroleptic malignant syndrome.

Mechanism of action

In contrast to most other neuroleptics which block both dopamine D₁ and D₂ receptors, sulpiride is more selective and acts primarily as a dopamine D₂ antagonist. Sulpiride appears to lack effects on norepinephrine, acetylcholine, serotonin, histamine, or gamma-aminobutyric acid (GABA) receptors.

Pharmacodynamics

Sulpiride is a substituted benzamide derivative and a selective dopamine D₂ antagonist with antipsychotic and antidepressant activity. Other benzamide derivatives include metoclopramide, tiapride, and sultopride.