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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 of LEVOSULPIRIDE

SMILES

CCN1CCC[C@H]1CNC(=O)C2=C(OC)C=CC(=C2)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

Description

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
51.0 nM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor.
1992 Apr 10
A double-blind study of L-sulpiride versus amitriptyline in lithium-maintained bipolar depressives.
1993 Dec
Pharmacological and functional characterization of D2, D3 and D4 dopamine receptors in fibroblast and dopaminergic cell lines.
1994 Jan
Expression and pharmacological characterization of the human D3 dopamine receptor.
1994 Jan
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
Identification and pharmacological characterization of [125I]L-750,667, a novel radioligand for the dopamine D4 receptor.
1996 Dec
Side-effects of benzamide derivatives.
1997 Jan
[Combination chemotherapy with Taxol and cisplatin for 57 patients with non-small cell lung cancer by intraartery and intravenous infusion].
2002 Dec
Improvement and validation of a liquid chromatographic method for the determination of levosulpiride in human serum and urine.
2003 Nov 5
Levosulpiride and cisapride in the treatment of dysmotility-like functional dyspepsia: a randomized, double-masked trial.
2004 Apr
Delayed Gastric Emptying in Functional Dyspepsia.
2004 Aug
Type 1 (insulin-dependent) diabetes mellitus and gastric emptying: role of blood glucose concentration and dopamine D2 receptors.
2004 Feb
Psychopharmacological treatment of depression, anxiety, irritability and insomnia in patients receiving interferon-alpha: a prospective case series and a discussion of biological mechanisms.
2004 Mar
Pharmacokinetics and bioequivalence evaluation of 2 levosulpiride preparations after a single oral dose in healthy male Korean volunteers.
2004 Mar
The impact of neuroleptic medication on seizure threshold and duration in electroconvulsive therapy.
2004 Nov 20
Hydrophilic interaction liquid chromatography-tandem mass spectrometry for the determination of levosulpiride in human plasma.
2004 Oct 5
BIM-23A760, a chimeric molecule directed towards somatostatin and dopamine receptors, vs universal somatostatin receptors ligands in GH-secreting pituitary adenomas partial responders to octreotide.
2005
[Two cases of tardive Tourette syndrome].
2006
Dose-dependent improvement of myoclonic hyperkinesia due to Valproic acid in eight Huntington's Disease patients: a case series.
2006 Feb 28
Prokinetic drug utility in the treatment of gastroesophageal reflux esophagitis: a systematic review of randomized controlled trials.
2007
[Characteristics of a combined course of duodenal ulcer and gastroesophageal reflux disease].
2007
Exposure to amlodipine in the first trimester of pregnancy and during breastfeeding.
2007
Effectiveness and safety of levosulpiride in the treatment of dysmotility-like functional dyspepsia.
2007 Mar
Drug-induced and psychogenic resting suprahyoid neck and tongue tremors.
2008 Apr 15
Triple reuptake inhibitors: the next generation of antidepressants.
2008 Dec
Development of membrane selective electrode for determination of the antipsychotic sulpiride in pharmaceuticals and urine.
2009
Levosulpiride-induced resting orolingual tremor.
2009 Aug 15
Rapid quantification of levosulpiride in human plasma using RP-HPLC-MS/MS for pharmacokinetic and bioequivalence study.
2009 Dec
Combination therapy of levosulpiride and lamotrigine associated with tardive dyskinesia.
2009 Feb
Teratogenicity and hyperprolactinemia.
2009 Jan
[Efficiacy of combined eglonil and avestin administration for pharmacocorrection of depressive disorders in women with hypoestrogenic syndrome].
2009 Jul-Aug
Determination of metoclopramide in human plasma using hydrophilic interaction chromatography with tandem mass spectrometry.
2009 Jun 15
Levosulpiride-induced movement disorders.
2009 Nov 15
Pharmacotherapy for gastroparesis: an attempt to evaluate a safer alternative.
2010 Oct
[Levosulpiride in the management of functional dyspepsia and delayed gastric emptying].
2010 Oct
Levosulpiride in premature ejaculation.
2010 Oct-Dec
Patents

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: oral, parenteral
Name Type Language
LEVOSULPIRIDE
INN   MART.   WHO-DD  
INN  
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
LEVOSULPIRIDE [WHO-DD]
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
MI  
Common Name English
LEVOBREN
Brand Name English
SULPIRIDE, (-)-
Common Name English
LESURIDE
Brand Name English
LEVOPRIDE
Brand Name English
LEVOSULPIRIDE [MART.]
Common Name English
(-)-SULPIRIDE
Common Name English
L-SULPIRIDE
Common Name English
Classification Tree Code System Code
WHO-ATC N05AL07
Created by admin on Tue Oct 22 06:07:18 UTC 2019 , Edited by admin on Tue Oct 22 06:07:18 UTC 2019
WHO-VATC QN05AL07
Created by admin on Tue Oct 22 06:07:18 UTC 2019 , Edited by admin on Tue Oct 22 06:07:18 UTC 2019
NCI_THESAURUS C66883
Created by admin on Tue Oct 22 06:07:18 UTC 2019 , Edited by admin on Tue Oct 22 06:07:18 UTC 2019
Code System Code Type Description
EPA CompTox
23672-07-3
Created by admin on Tue Oct 22 06:07:18 UTC 2019 , Edited by admin on Tue Oct 22 06:07:18 UTC 2019
PRIMARY
CAS
23672-07-3
Created by admin on Tue Oct 22 06:07:18 UTC 2019 , Edited by admin on Tue Oct 22 06:07:18 UTC 2019
PRIMARY
MERCK INDEX
M10389
Created by admin on Tue Oct 22 06:07:18 UTC 2019 , Edited by admin on Tue Oct 22 06:07:18 UTC 2019
PRIMARY Merck Index
INN
6593
Created by admin on Tue Oct 22 06:07:18 UTC 2019 , Edited by admin on Tue Oct 22 06:07:18 UTC 2019
PRIMARY
NCI_THESAURUS
C90840
Created by admin on Tue Oct 22 06:07:18 UTC 2019 , Edited by admin on Tue Oct 22 06:07:18 UTC 2019
PRIMARY
IUPHAR
958
Created by admin on Tue Oct 22 06:07:18 UTC 2019 , Edited by admin on Tue Oct 22 06:07:18 UTC 2019
PRIMARY
ChEMBL
CHEMBL267044
Created by admin on Tue Oct 22 06:07:18 UTC 2019 , Edited by admin on Tue Oct 22 06:07:18 UTC 2019
PRIMARY
MESH
C078143
Created by admin on Tue Oct 22 06:07:18 UTC 2019 , Edited by admin on Tue Oct 22 06:07:18 UTC 2019
PRIMARY
EVMPD
SUB08494MIG
Created by admin on Tue Oct 22 06:07:18 UTC 2019 , Edited by admin on Tue Oct 22 06:07:18 UTC 2019
PRIMARY
WIKIPEDIA
LEVOSULPIRIDE
Created by admin on Tue Oct 22 06:07:18 UTC 2019 , Edited by admin on Tue Oct 22 06:07:18 UTC 2019
PRIMARY
PUBCHEM
688272
Created by admin on Tue Oct 22 06:07:18 UTC 2019 , Edited by admin on Tue Oct 22 06:07:18 UTC 2019
PRIMARY