Levosulpiride

Levosulpiride, sold under the brand names Dislep and Sulpepta among others, is a dopamine antagonist medication which is used in the treatment of psychotic disorders like schizophrenia, major depressive disorder, nausea and vomiting, and gastroparesis.^[1][2][3][4] It is taken by mouth.

Levosulpiride

Clinical data
Trade names	Dislep, Sulpepta, others
Other names	L-Sulpiride; S-(–)-Sulpiride; RV-12309
Routes of administration	Oral
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	DB16021
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
(verify)

It is a selective antagonist of the dopamine D₂ receptor and an agonist of the serotonin 5-HT₄ receptor.^[4][5] Chemically, it is a benzamide and the (S)-(−)-enantiomer of sulpiride.^[4]

Levosulpiride is marketed widely throughout the world, including in Europe, South Korea, Latin America, India, and Pakistan.^[2] It is not available in the United States or the United Kingdom.^[2]

Medical uses

Levosulpiride is used in the treatment of:^[3][1]

• Psychosis
• Negative symptoms of schizophrenia
• Major depressive disorder
• Anxiety disorders
• Dysthymia
• Vertigo
• Nausea and vomiting
• Gastroparesis
• Dyspepsia
• Irritable bowel syndrome
• Premature ejaculation^[6][7]

Levosulpiride is not currently licensed for treatment of premature ejaculation in the United Kingdom or other European countries.^[8]

Side effects

Side effects of levosulpiride include amenorrhea, gynecomastia, galactorrhea, changes in libido, and neuroleptic malignant syndrome.^[9] In the United States, as of 2013 only one case of adverse reaction to levosulpiride had been recorded on the FDA Adverse Event Reporting System Database.^[8] A case of rapid-onset resistant dystonia caused by low-dose levosulpiride was reported in India.^[10]

Pharmacology

Pharmacodynamics

Levosulpiride is a selective dopamine D₂ receptor antagonist.^[4] The drug has also been found to act as a moderate agonist of the serotonin 5-HT₄ receptor.^[5] It is said to have antipsychotic, antidepressant, antiemetic, and gastroprokinetic effects.^[4]

Chemistry

Levosulpiride is a substituted benzamide derivative.^[4] It is the levorotatory enantiomer of sulpiride.^[4] Other benzamide derivatives include amisulpride, metoclopramide, tiapride, sultopride, and veralipride, among others.