Levosulpiride

Levosulpiride

Names
IUPAC name N-[[(2S)-(−)-1-ethylpyrrolidin-2-yl]methyl]-2-methoxy-5-sulfamoylbenzamide
Identifiers
CAS Number	23672-07-3 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:4119 N
ChemSpider	599749 N
IUPHAR/BPS	958
KEGG	D07312 Y
PubChem CID	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 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (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.

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

Levosulpiride is used in the treatment of:

Levosulpiride is not currently licensed for treatment of premature ejaculation in the UK or other European countries.

Side effects include amenorrhea, gynecomastia, galactorrhea, changes in libido, and neuroleptic malignant syndrome. In the U.S., as of 2013 only one case of adverse reaction to Levosulpiride had been recorded on the FDA Adverse Event Reporting System Database. A case of rapid onset resistant dystonia (involuntary movements of the trunk, lips, and arms) caused by low dose levosulpiride was reported in India.

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.

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