Levosulpiride

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)

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.

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]

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.

References

^ ^a ^b "Levosulpiride". AdisInsight. 24 October 2021. Retrieved 22 October 2024.
^ ^a ^b ^c "Levosulpiride (International database)". Drugs.com. 6 October 2024. Retrieved 22 October 2024.
^ ^a ^b Mucci A, Nolfe G, Maj M (February 1995). "Levosulpiride: a review of its clinical use in psychiatry". Pharmacol Res. 31 (2): 95–101. doi:10.1016/1043-6618(95)80053-0. PMID 7596960.
^ ^a ^b ^c ^d ^e ^f ^g Rossi F, Forgione A (February 1995). "Pharmacotoxicological aspects of levosulpiride". Pharmacol Res. 31 (2): 81–94. doi:10.1016/1043-6618(95)80052-2. PMID 7596959.
^ ^a ^b Tonini M, De Giorgio R, Spelta V, Bassotti G, Di Nucci A, Anselmi L, Balestra B, De Ponti F (April 2003). "5-HT4 receptors contribute to the motor stimulating effect of levosulpiride in the guinea-pig gastrointestinal tract". Dig Liver Dis. 35 (4): 244–250. doi:10.1016/s1590-8658(03)00061-6. PMID 12801035.
^ Arshad A, Irfan M, Inam M, Hussain NH, Ismail SB (2022). "Levosulpiride for Premature Ejaculation: A Systematic Review and Meta-Analysis". Am J Mens Health. 16 (5): 15579883221124832. doi:10.1177/15579883221124832. PMC 9515538. PMID 36154321.
^ Greco E, Polonio-Balbi P, Speranza JC (August 2002). "Levosulpiride: a new solution for premature ejaculation?". Int J Impot Res. 14 (4): 308–309. doi:10.1038/sj.ijir.3900901. PMID 12152121.
^ ^a ^b 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.
^ "Levosulpiride drug information". DrugsUpdate India.
^ 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.

[AdisInsight-1] "Levosulpiride". AdisInsight. 24 October 2021. Retrieved 22 October 2024.

[Drugs.com-International-2] "Levosulpiride (International database)". Drugs.com. 6 October 2024. Retrieved 22 October 2024.

[MucciNolfeMaj1995-3] Mucci A, Nolfe G, Maj M (February 1995). "Levosulpiride: a review of its clinical use in psychiatry". Pharmacol Res. 31 (2): 95–101. doi:10.1016/1043-6618(95)80053-0. PMID 7596960.

[RossiForgione1995-4] ^ ^a ^b ^c ^d ^e ^f ^g Rossi F, Forgione A (February 1995). "Pharmacotoxicological aspects of levosulpiride". Pharmacol Res. 31 (2): 81–94. doi:10.1016/1043-6618(95)80052-2. PMID 7596959.

[ToniniDeGiorgioSpelta2003-5] Tonini M, De Giorgio R, Spelta V, Bassotti G, Di Nucci A, Anselmi L, Balestra B, De Ponti F (April 2003). "5-HT4 receptors contribute to the motor stimulating effect of levosulpiride in the guinea-pig gastrointestinal tract". Dig Liver Dis. 35 (4): 244–250. doi:10.1016/s1590-8658(03)00061-6. PMID 12801035.

[ArshadIrfanInam2022-6] Arshad A, Irfan M, Inam M, Hussain NH, Ismail SB (2022). "Levosulpiride for Premature Ejaculation: A Systematic Review and Meta-Analysis". Am J Mens Health. 16 (5): 15579883221124832. doi:10.1177/15579883221124832. PMC 9515538. PMID 36154321.

[GrecoPolonio-Balbi2002-7] Greco E, Polonio-Balbi P, Speranza JC (August 2002). "Levosulpiride: a new solution for premature ejaculation?". Int J Impot Res. 14 (4): 308–309. doi:10.1038/sj.ijir.3900901. PMID 12152121.

[Poluzzi_2013-8] 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.

[9] "Levosulpiride drug information". DrugsUpdate India.

[10] 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.

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