Levosulpiride

Levosulpiride
Clinical data
ATC code	N05AL07 (WHO) ;
Identifiers
	IUPAC name N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2-methoxy-5-sulfamoylbenzamide;
CAS Number	23672-07-3;
PubChem CID	688272;
IUPHAR/BPS	958;
DrugBank	DB00391;
ChemSpider	599749;
UNII	JTG7R315LK;
KEGG	D07312;
ChEBI	CHEBI:64119;
ChEMBL	ChEMBL267044;
CompTox Dashboard (EPA)	DTXSID0042583;
Chemical and physical data
Formula	C15H23N3O4S
Molar mass	341.43 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN1CCC[C@H]1CNC(=O)C2=C(C=CC(=C2)S(=O)(=O)N)OC;
	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; Key:BGRJTUBHPOOWDU-NSHDSACASA-N;
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Levosulpiride, sold under the brand name SULPEPTA , is a potent prokinetic agent of the benzamide class.^[1] It is a selective antagonist of the dopamine D₂ receptors and 5HT4 Agonism ^[2] on both central and peripheral nervous systems. Levosulpiride is claimed to have mood elevating properties.

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

Uses

Levosulpiride is used in the treatment of:

Levosulpiride is not currently licensed for treatment of premature ejaculation in the UK or other European countries.^[3]

Side effects

Side effects include amenorrhea, gynecomastia, galactorrhea, changes in libido, and neuroleptic malignant syndrome.^[4] 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.^[3] A case of rapid onset resistant dystonia caused by low dose levosulpiride was reported in India.^[5]

Mechanism of action

In contrast to most other neuroleptics which block both D₁ and D₂ receptors, levosulpiride is more selective and acts primarily as a D₂ antagonist. Levosulpiride appears to lack effects on norepinephrine, acetylcholine, serotonin, histamine, and gamma-aminobutyric acid (GABA) receptors.^[6]

Pharmacodynamics

Levosulpiride is a substituted benzamide derivative and a selective dopamine D₂ antagonist with antipsychotic and antidepressant activity. Other benzamide derivatives include metoclopramide, tiapride, and sultopride.^[6]