Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H23N3O4S.ClH |
| Molecular Weight | 377.887 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCN1CCC[C@H]1CNC(=O)C2=CC(=CC=C2OC)S(N)(=O)=O
InChI
InChIKey=PFHZICSPLHQCDZ-MERQFXBCSA-N
InChI=1S/C15H23N3O4S.ClH/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);1H/t11-;/m0./s1
| 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 |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator'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
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 |
|---|---|---|---|
Target ID: CHEMBL217 |
51.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Levopraid Approved UseLevosulpiride 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. |
|||
| Primary | Unknown Approved UseLevosulpiride 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. |
|||
| Primary | Levopraid Approved UseLevosulpiride 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. |
|||
| Primary | Levopraid Approved UseLevosulpiride 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. |
|||
| Primary | Unknown Approved UseLevosulpiride 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. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
441 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26579410/ |
25 mg single, intramuscular dose: 25 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
LEVOSULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
823 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26579410/ |
50 mg single, intramuscular dose: 50 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
LEVOSULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
539 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26579410/ |
25 mg 2 times / day multiple, intramuscular dose: 25 mg route of administration: Intramuscular experiment type: MULTIPLE co-administered: |
LEVOSULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
73 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19488984/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVOSULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1724 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26579410/ |
25 mg single, intramuscular dose: 25 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
LEVOSULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
3478 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26579410/ |
50 mg single, intramuscular dose: 50 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
LEVOSULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
2146 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26579410/ |
25 mg 2 times / day multiple, intramuscular dose: 25 mg route of administration: Intramuscular experiment type: MULTIPLE co-administered: |
LEVOSULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
874 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19488984/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVOSULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26579410/ |
25 mg single, intramuscular dose: 25 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
LEVOSULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
6.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26579410/ |
50 mg single, intramuscular dose: 50 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
LEVOSULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
7.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26579410/ |
25 mg 2 times / day multiple, intramuscular dose: 25 mg route of administration: Intramuscular experiment type: MULTIPLE co-administered: |
LEVOSULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
8.77 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19488984/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVOSULPIRIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
86% |
LEVOSULPIRIDE plasma | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
50 mg single, intravenous Highest studied dose Dose: 50 mg Route: intravenous Route: single Dose: 50 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
75 mg single, intramuscular Highest studied dose Dose: 75 mg Route: intramuscular Route: single Dose: 75 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
800 mg multiple, oral Highest studied dose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
75 mg 3 times / day multiple, oral Recommended Dose: 75 mg, 3 times / day Route: oral Route: multiple Dose: 75 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Orolingual tremor... AEs leading to discontinuation/dose reduction: Orolingual tremor Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Orolingual tremor | Disc. AE | 75 mg 3 times / day multiple, oral Recommended Dose: 75 mg, 3 times / day Route: oral Route: multiple Dose: 75 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Levosulpiride in premature ejaculation. | 2012-03-30 |
|
| Pharmacotherapy for gastroparesis: an attempt to evaluate a safer alternative. | 2010-10 |
|
| [Levosulpiride in the management of functional dyspepsia and delayed gastric emptying]. | 2010-10 |
|
| Liquid chromatography-tandem mass spectrometry quantification of levosulpiride in human plasma and its application to bioequivalence study. | 2010-08-15 |
|
| Influence of ABCB1 genetic polymorphisms on the pharmacokinetics of levosulpiride in healthy subjects. | 2010-08-11 |
|
| A randomised controlled study of risperidone and olanzapine for schizophrenic patients with neuroleptic-induced acute dystonia or parkinsonism. | 2010-01 |
|
| Aripiprazole Improves Depressive Symptoms and Immunological Response to Antiretroviral Therapy in an HIV-Infected Subject with Resistant Depression. | 2010 |
|
| Rapid quantification of levosulpiride in human plasma using RP-HPLC-MS/MS for pharmacokinetic and bioequivalence study. | 2009-12 |
|
| Levosulpiride-induced movement disorders. | 2009-11-15 |
|
| [Efficiacy of combined eglonil and avestin administration for pharmacocorrection of depressive disorders in women with hypoestrogenic syndrome]. | 2009-10-07 |
|
| Diabetes mellitus and drug-induced Parkinsonism: a case-control study. | 2009-09-15 |
|
| Gastroparesis: current concepts and management. | 2009-09 |
|
| Levosulpiride-induced resting orolingual tremor. | 2009-08-15 |
|
| Determination of metoclopramide in human plasma using hydrophilic interaction chromatography with tandem mass spectrometry. | 2009-06-15 |
|
| Associations among hair loss, oral sulfur-containing gases, and gastrointestinal and metabolic linked diseases in Japanese elderly men: pilot study. | 2009-03-13 |
|
| Combination therapy of levosulpiride and lamotrigine associated with tardive dyskinesia. | 2009-02 |
|
| Teratogenicity and hyperprolactinemia. | 2009-01 |
|
| Development of membrane selective electrode for determination of the antipsychotic sulpiride in pharmaceuticals and urine. | 2009 |
|
| Triple reuptake inhibitors: the next generation of antidepressants. | 2008-12 |
|
| [Major gastrointestinal syndromes (2): dyspepsia or syndrome of the upper digestive system related with food (2)]. | 2008-10-30 |
|
| Triple reuptake inhibitors: a premise and promise. | 2008-09 |
|
| Drug-induced and psychogenic resting suprahyoid neck and tongue tremors. | 2008-04-15 |
|
| Long-term Ultrasonographic Follow-up Study of Gastric Motility in Patients with Functional Dyspepsia. | 2008-03 |
|
| Clinical outcome of rumination syndrome in adults without psychiatric illness: a prospective study. | 2007-11 |
|
| Effectiveness and safety of levosulpiride in the treatment of dysmotility-like functional dyspepsia. | 2007-03 |
|
| The effect of levosulpiride in burning mouth syndrome. | 2007-02-09 |
|
| Prokinetic drug utility in the treatment of gastroesophageal reflux esophagitis: a systematic review of randomized controlled trials. | 2007 |
|
| [The effect of sulpirid in treatment of patients with gastric and duodenal erosions and ulcers]. | 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 |
|
| Clinical Implications of Cardiac-MIBG SPECT in the Differentiation of Parkinsonian Syndromes. | 2006-03 |
|
| Dose-dependent improvement of myoclonic hyperkinesia due to Valproic acid in eight Huntington's Disease patients: a case series. | 2006-02-28 |
|
| [Two cases of tardive Tourette syndrome]. | 2006 |
|
| Effects of l-stepholidine on forebrain Fos expression: comparison with clozapine and haloperidol. | 2005-02 |
|
| 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 |
|
| The analysis of characteristics of elderly people with high VSC level. | 2005 |
|
| The impact of neuroleptic medication on seizure threshold and duration in electroconvulsive therapy. | 2004-11-20 |
|
| Hydrophilic interaction liquid chromatography-tandem mass spectrometry for the determination of levosulpiride in human plasma. | 2004-10-05 |
|
| Delayed Gastric Emptying in Functional Dyspepsia. | 2004-08 |
|
| Development of HPLC method for the determination of levosulpiride in human plasma. | 2004-06-29 |
|
| Improvement of vestibular compensation by Levo-sulpiride in acute unilateral labyrinthine dysfunction. | 2004-04 |
|
| Levosulpiride and cisapride in the treatment of dysmotility-like functional dyspepsia: a randomized, double-masked trial. | 2004-04 |
|
| Psychopharmacological treatment of depression, anxiety, irritability and insomnia in patients receiving interferon-alpha: a prospective case series and a discussion of biological mechanisms. | 2004-03 |
|
| Type 1 (insulin-dependent) diabetes mellitus and gastric emptying: role of blood glucose concentration and dopamine D2 receptors. | 2004-02 |
|
| Side-effects of benzamide derivatives. | 1997-01 |
|
| Identification and pharmacological characterization of [125I]L-750,667, a novel radioligand for the dopamine D4 receptor. | 1996-12 |
|
| A randomized, double-blind, cross-over study comparing a levosulpiride-based and a metoclopramide-based combination in the prevention of ProMECE-CytaBOM-induced emesis. | 1995-09-01 |
|
| Pharmacological and functional characterization of D2, D3 and D4 dopamine receptors in fibroblast and dopaminergic cell lines. | 1994-01 |
|
| Expression and pharmacological characterization of the human D3 dopamine receptor. | 1994-01 |
|
| A double-blind study of L-sulpiride versus amitriptyline in lithium-maintained bipolar depressives. | 1993-12 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Apr 01 16:43:19 GMT 2025
by
admin
on
Tue Apr 01 16:43:19 GMT 2025
|
| Record UNII |
3400N2ZP5P
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
3400N2ZP5P
Created by
admin on Tue Apr 01 16:43:19 GMT 2025 , Edited by admin on Tue Apr 01 16:43:19 GMT 2025
|
PRIMARY | |||
|
77111-58-1
Created by
admin on Tue Apr 01 16:43:19 GMT 2025 , Edited by admin on Tue Apr 01 16:43:19 GMT 2025
|
PRIMARY | |||
|
121490096
Created by
admin on Tue Apr 01 16:43:19 GMT 2025 , Edited by admin on Tue Apr 01 16:43:19 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
RACEMATE -> ENANTIOMER |
