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
A double-blind study of L-sulpiride versus amitriptyline in lithium-maintained bipolar depressives.	1993 Dec	8310852
Pharmacological and functional characterization of D2, D3 and D4 dopamine receptors in fibroblast and dopaminergic cell lines.	1994 Jan	8301592
Expression and pharmacological characterization of the human D3 dopamine receptor.	1994 Jan	8301582
A randomized, double-blind, cross-over study comparing a levosulpiride-based and a metoclopramide-based combination in the prevention of ProMECE-CytaBOM-induced emesis.	1995 Sep-Oct	8566881
Identification and pharmacological characterization of [125I]L-750,667, a novel radioligand for the dopamine D4 receptor.	1996 Dec	8967990
Side-effects of benzamide derivatives.	1997 Jan	9050439
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
Delayed Gastric Emptying in Functional Dyspepsia.	2004 Aug	15238200
Development of HPLC method for the determination of levosulpiride in human plasma.	2004 Jun 29	15193738
The impact of neuroleptic medication on seizure threshold and duration in electroconvulsive therapy.	2004 Nov 20	15662766
The analysis of characteristics of elderly people with high VSC level.	2005	15752107
Effects of l-stepholidine on forebrain Fos expression: comparison with clozapine and haloperidol.	2005 Feb	15578005
Dose-dependent improvement of myoclonic hyperkinesia due to Valproic acid in eight Huntington's Disease patients: a case series.	2006 Feb 28	16507108
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
[The effect of sulpirid in treatment of patients with gastric and duodenal erosions and ulcers].	2007	17882817
[Characteristics of a combined course of duodenal ulcer and gastroesophageal reflux disease].	2007	17523407
Exposure to amlodipine in the first trimester of pregnancy and during breastfeeding.	2007	17469008
Effectiveness and safety of levosulpiride in the treatment of dysmotility-like functional dyspepsia.	2007 Mar	18360622
Clinical outcome of rumination syndrome in adults without psychiatric illness: a prospective study.	2007 Nov	17914944
Drug-induced and psychogenic resting suprahyoid neck and tongue tremors.	2008 Apr 15	18186115
Triple reuptake inhibitors: the next generation of antidepressants.	2008 Dec	19587855
[Major gastrointestinal syndromes (2): dyspepsia or syndrome of the upper digestive system related with food (2)].	2008 Jul-Sep	18958143
Long-term Ultrasonographic Follow-up Study of Gastric Motility in Patients with Functional Dyspepsia.	2008 Mar	18385832
Development of membrane selective electrode for determination of the antipsychotic sulpiride in pharmaceuticals and urine.	2009	22408528
Levosulpiride-induced resting orolingual tremor.	2009 Aug 15	19452563
Rapid quantification of levosulpiride in human plasma using RP-HPLC-MS/MS for pharmacokinetic and bioequivalence study.	2009 Dec	19488984
Combination therapy of levosulpiride and lamotrigine associated with tardive dyskinesia.	2009 Feb	19165957
Determination of metoclopramide in human plasma using hydrophilic interaction chromatography with tandem mass spectrometry.	2009 Jun 15	19442594
Associations among hair loss, oral sulfur-containing gases, and gastrointestinal and metabolic linked diseases in Japanese elderly men: pilot study.	2009 Mar 13	19284665
Levosulpiride-induced movement disorders.	2009 Nov 15	19795476
Gastroparesis: current concepts and management.	2009 Sep	20431741
Diabetes mellitus and drug-induced Parkinsonism: a case-control study.	2009 Sep 15	19467671
Aripiprazole Improves Depressive Symptoms and Immunological Response to Antiretroviral Therapy in an HIV-Infected Subject with Resistant Depression.	2010	20369069
Influence of ABCB1 genetic polymorphisms on the pharmacokinetics of levosulpiride in healthy subjects.	2010 Aug 11	20438811
Liquid chromatography-tandem mass spectrometry quantification of levosulpiride in human plasma and its application to bioequivalence study.	2010 Aug 15	20656570
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
[Levosulpiride in the management of functional dyspepsia and delayed gastric emptying].	2010 Oct	20850200
Levosulpiride in premature ejaculation.	2010 Oct-Dec	22455278

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

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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