LEVOSULPIRIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H23N3O4S
Molecular Weight	341.426
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1CCC[C@H]1CNC(=O)C2=CC(=CC=C2OC)S(N)(=O)=O

InChI

InChIKey=BGRJTUBHPOOWDU-NSHDSACASA-N

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

HIDE SMILES / InChI

Molecular Formula	C15H23N3O4S
Molecular Weight	341.426
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://adisinsight.springer.com/drugs/800003554
Curator's Comment: Description was created based on several sources, including http://medind.nic.in/daa/t07/i2/daat07i2p144.pdf | http://www.druginfosys.com/drug.aspx?drugcode=1180&type=1

Levosulpiride [RV 12309, L-sulpiride, levosulpride, Dislep® 25, Levopride®, Levopraid®] is a potent dopamine D2 receptor blocker that was originated by Ravizza Farmaceutici (now AbbVie). Levosulpiride is the levo enantiomer of sulpiride. The levo enantiomer shows better/similar pharmacological actions and lower incidence of toxic effects than both dextro as well as the racemic forms of the drug. Levosulpiride is marketed in Italy and South Korea, and is possibly available elsewhere in Europe and Asia. Levosulpiride does not appear to be available in North America. Levosulpiride is available as 25mg tablets, drops and in ampoules for parenteral administration. Generic versions of levosulpiride also appear to be available in some countries. Levosulpiride is primarily indicated in conditions like Anxiety, Depression, Gastro-esophageal reflux disease, Irritable bowel syndrome, Schizophrenia, Tourette's syndrome, dyspeptic syndrome, essential cephalgia, and can also be given in adjunctive therapy as an alternative drug of choice in Peptic ulcer, Vertigo.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: http://adisinsight.springer.com/drugs/800003554	Antagonist 2778		51.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Dyspepsia 11 Sources: http://adisinsight.springer.com/drugs/800003554	Primary	Approved 8429	Levopraid Approved Use Levosulpiride is primarily indicated in conditions like Anxiety, Depression, Gastro-esophageal reflux disease, Irritable bowel syndrome, Schizophrenia, Tourette's syndrome, dyspeptic syndrome, essential cephalgia, and can also be given in adjunctive therapy as an alternative drug of choice in Peptic ulcer, Vertigo.
Schizophrenia 298 Sources: http://adisinsight.springer.com/drugs/800003554	Primary	Approved 8429	Unknown Approved Use Levosulpiride is primarily indicated in conditions like Anxiety, Depression, Gastro-esophageal reflux disease, Irritable bowel syndrome, Schizophrenia, Tourette's syndrome, dyspeptic syndrome, essential cephalgia, and can also be given in adjunctive therapy as an alternative drug of choice in Peptic ulcer, Vertigo.
Essential cephalgia 2 Sources: http://www.druginfosys.com/drug.aspx?drugcode=1180&type=1	Primary	Approved 8429	Levopraid Approved Use Levosulpiride is primarily indicated in conditions like Anxiety, Depression, Gastro-esophageal reflux disease, Irritable bowel syndrome, Schizophrenia, Tourette's syndrome, dyspeptic syndrome, essential cephalgia, and can also be given in adjunctive therapy as an alternative drug of choice in Peptic ulcer, Vertigo.
Vertigo 17 Sources: http://www.druginfosys.com/drug.aspx?drugcode=1180&type=1	Primary	Approved 8429	Levopraid Approved Use Levosulpiride is primarily indicated in conditions like Anxiety, Depression, Gastro-esophageal reflux disease, Irritable bowel syndrome, Schizophrenia, Tourette's syndrome, dyspeptic syndrome, essential cephalgia, and can also be given in adjunctive therapy as an alternative drug of choice in Peptic ulcer, Vertigo.
Major depressive disorder 173 Sources: http://adisinsight.springer.com/drugs/800003554	Primary	Approved 8429	Unknown Approved Use Levosulpiride is primarily indicated in conditions like Anxiety, Depression, Gastro-esophageal reflux disease, Irritable bowel syndrome, Schizophrenia, Tourette's syndrome, dyspeptic syndrome, essential cephalgia, and can also be given in adjunctive therapy as an alternative drug of choice in Peptic ulcer, Vertigo.

PubMed

Title	Date	PubMed
Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor.	1992 Apr 10	1354163
Expression and pharmacological characterization of the human D3 dopamine receptor.	1994 Jan	8301582
Identification and pharmacological characterization of [125I]L-750,667, a novel radioligand for the dopamine D4 receptor.	1996 Dec	8967990
[Combination chemotherapy with Taxol and cisplatin for 57 patients with non-small cell lung cancer by intraartery and intravenous infusion].	2002 Dec	12520750
Effect of acute and chronic levosulpiride administration on gastric tone and perception in functional dyspepsia.	2002 Mar	11876717
Improvement and validation of a liquid chromatographic method for the determination of levosulpiride in human serum and urine.	2003 Nov 5	14581065
Improvement of vestibular compensation by Levo-sulpiride in acute unilateral labyrinthine dysfunction.	2004 Apr	15468991
Levosulpiride and cisapride in the treatment of dysmotility-like functional dyspepsia: a randomized, double-masked trial.	2004 Apr	15067624
Delayed Gastric Emptying in Functional Dyspepsia.	2004 Aug	15238200
Review article: clinical implications of enteric and central D2 receptor blockade by antidopaminergic gastrointestinal prokinetics.	2004 Feb 15	14871277
Pharmacokinetics and bioequivalence evaluation of 2 levosulpiride preparations after a single oral dose in healthy male Korean volunteers.	2004 Mar	15049438
The impact of neuroleptic medication on seizure threshold and duration in electroconvulsive therapy.	2004 Nov 20	15662766
Clinical Implications of Cardiac-MIBG SPECT in the Differentiation of Parkinsonian Syndromes.	2006 Mar	20396485
Prokinetic drug utility in the treatment of gastroesophageal reflux esophagitis: a systematic review of randomized controlled trials.	2007	21673949
[Characteristics of a combined course of duodenal ulcer and gastroesophageal reflux disease].	2007	17523407
The effect of levosulpiride in burning mouth syndrome.	2007 Jan-Feb	17287703
[Major gastrointestinal syndromes (2): dyspepsia or syndrome of the upper digestive system related with food (2)].	2008 Jul-Sep	18958143
Teratogenicity and hyperprolactinemia.	2009 Jan	19742198
Determination of metoclopramide in human plasma using hydrophilic interaction chromatography with tandem mass spectrometry.	2009 Jun 15	19442594
Levosulpiride-induced movement disorders.	2009 Nov 15	19795476
Aripiprazole Improves Depressive Symptoms and Immunological Response to Antiretroviral Therapy in an HIV-Infected Subject with Resistant Depression.	2010	20369069
A randomised controlled study of risperidone and olanzapine for schizophrenic patients with neuroleptic-induced acute dystonia or parkinsonism.	2010 Jan	18801830
Pharmacotherapy for gastroparesis: an attempt to evaluate a safer alternative.	2010 Oct	21103416

Patents

Sample Use Guides

In Vivo Use Guide

dosage depends on indication: 200 to 800 mg, 24 hourly, IM; 200 to 400 mg, 12 hourly, PO; 25 mg, 8 hourly, PO

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:07:37 GMT 2023` Edited by `admin` on `Fri Dec 15 16:07:37 GMT 2023`
Record UNII	JTG7R315LK
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LEVOSULPIRIDE

Official Name

English

SULPIRIDE, (S)-

Common Name

English

LEVOPRAID

Brand Name

English

SULPIRIDE L-FORM [MI]

Common Name

English

(-)-N-(((S)-1-ETHYL-2-PYRROLIDINYL)METHYL)-5-SULFAMOYL-O-ANISAMIDE

Common Name

English

S-(-)-SULPIRIDE

Common Name

English

levosulpiride [INN]

Common Name

English

BENZAMIDE, 5-(AMINOSULFONYL)-N-(((2S)-1-ETHYL-2-PYRROLIDINYL)METHYL)-2-METHOXY-

Systematic Name

English

SULPIRIDE L-FORM

Common Name

English

LEVOBREN

Brand Name

English

SULPIRIDE, (-)-

Common Name

English

LESURIDE

Brand Name

English

LEVOPRIDE

Brand Name

English

LEVOSULPIRIDE [MART.]

Common Name

English

Levosulpiride [WHO-DD]

Common Name

English

(-)-SULPIRIDE

Common Name

English

L-SULPIRIDE

Common Name

English

Classification Tree Code System Code

WHO-ATC

N05AL07