Levosulpiride

Levosulpiride, sold under the brand name Neoprad, is a typical antipsychotic and a prokinetic agent of the benzamide class.[1] It is a selective antagonist of the dopamine D2 receptors[2] on both central and peripheral nervous systems. Levosulpiride is claimed to have mood elevating properties.

Levosulpiride
Clinical data
ATC code
Identifiers
IUPAC name
  • N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2-methoxy-5-sulfamoylbenzamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H23N3O4S
Molar mass341.43 g·mol−1
3D model (JSmol)
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
 NY (what is this?)  (verify)

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]

See also

References
  1. "Levosulpiride - S-(-)-Sulpiride". Generon. Retrieved 2016-08-31.
  2. "Levosulpiride". Stratech Scientific Ltd. Retrieved 2016-08-31.
  3. Poluzzi E, Raschi E, Koci A, Moretti U, Spina E, Behr ER, et al. (June 2013). "Antipsychotics and torsadogenic risk: signals emerging from the US FDA Adverse Event Reporting System database". Drug Safety. 36 (6): 467–79. doi:10.1007/s40264-013-0032-z. PMC 3664739. PMID 23553446.
  4. "Levosulpiride drug information". DrugsUpdate India.
  5. Naskar S, Nath K (January 2007). "Rapid onset resistant dystonia with low dose of Levosulpiride". British Journal of Psychiatry. 190 (1): 81. doi:10.1192/bjp.190.1.81a.
  6. "Sulpiride". DrugBank. DB00391.
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