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
ChEMBL	ChEMBL267044 N
ChemSpider	599749 N
IUPHAR/BPS	958
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 (WHO)
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,^[1] reported to be a selective antagonist of dopamine D₂ receptor activity ^[2]on both central and peripheral levels. It is an atypical neuroleptic and a prokinetic agent.^[2] Levosulpiride is also claimed to have mood elevating properties.

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

Uses

Levosulpiride is used in the treatment of:

• psychoses
• particularly negative symptoms of schizophrenia
• anxiety disorders
• dysthymia
• vertigo
• dyspepsia
• irritable bowel syndrome
• premature ejaculation.

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

Side effect

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.^[5] A case of rapid onset resistant dystonia (involuntary movements of the trunk, lips, and arms) caused by low dose levosulpiride was reported in India.^[6]

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. ^[7]

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.^[8]

References