NAV

Rebamipide

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Rebamipide is a gastroprotective agent used in combination with other similar therapies (e.g. proton pump inhibitors) to treat gastritis and protect the gastric mucosa.

Generic Name
Rebamipide
DrugBank Accession Number
DB11656
Background

Rebamipide has been investigated for the treatment of Stomach Ulcer, Keratoconjunctivitis Sicca, and Gastric Adenoma and Early Gastric Cancer.

Type
Small Molecule
Groups
Approved, Investigational
Structure
3D
Similar Structures
Weight
Average: 370.79
Monoisotopic: 370.0720347
Chemical Formula
C19H15ClN2O4
Synonyms
  • Rebamipida
  • Rebamipide
  • Rébamipide
  • Rebamipidum
External IDs
  • OPC 12759
  • OPC-12759
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Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Adjunct therapy in treatment ofGastric ulcer••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
  • Take with or without food. Food does not impact the bioavailability of rebamipide.

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International/Other Brands
Mucosta

Categories

ATC Codes
A02BX14 — Rebamipide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hippuric acids. These are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Hippuric acids
Alternative Parents
N-acyl-alpha amino acids / Quinolones and derivatives / Hydroxyquinolines / 4-halobenzoic acids and derivatives / Benzoyl derivatives / Hydroxypyridines / Chlorobenzenes / Aryl chlorides / Heteroaromatic compounds / Secondary carboxylic acid amides
show 9 more
Substituents
4-halobenzoic acid or derivatives / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzoyl / Carbonyl group / Carboxamide group / Carboxylic acid
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
LR583V32ZR
CAS number
90098-04-7
InChI Key
ALLWOAVDORUJLA-UHFFFAOYSA-N
InChI
InChI=1S/C19H15ClN2O4/c20-13-7-5-11(6-8-13)18(24)22-16(19(25)26)9-12-10-17(23)21-15-4-2-1-3-14(12)15/h1-8,10,16H,9H2,(H,21,23)(H,22,24)(H,25,26)
IUPAC Name
2-[(4-chlorophenyl)formamido]-3-(2-oxo-1,2-dihydroquinolin-4-yl)propanoic acid
SMILES
OC(=O)C(CC1=CC(=O)NC2=C1C=CC=C2)NC(=O)C1=CC=C(Cl)C=C1

References

General References
  1. BPOM Drug Information: Rebamipide for oral use [Link]
PubChem Compound
5042
PubChem Substance
347828027
ChemSpider
4866
ChEBI
93814
ChEMBL
CHEMBL1697771
Wikipedia
Rebamipide

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4CompletedTreatmentDry Eye Syndrome (DES) / Sjogren's Syndrome (SS)1
4CompletedTreatmentGastric Ulcer2
4CompletedTreatmentGastritis1
4CompletedTreatmentGastritis Acute / Gastritis Chronic1
4CompletedTreatmentGastroesophageal Reflux1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet100 mg
Tablet, film coatedOral
Granule
Tablet, film coatedOral100 mg
Tablet, coatedOral100 mg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0103 mg/mLALOGPS
logP2.32ALOGPS
logP2.76Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.52Chemaxon
pKa (Strongest Basic)-1.1Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area95.5 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity98.5 m3·mol-1Chemaxon
Polarizability36.82 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00xr-0698000000-68b14bd14b18bae9a8c5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0029000000-baad81f7e12e22d20076
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gi0-0729000000-6f267244436db56c30b6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dr-0629000000-f2d700a464649e5cdcf9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-2809000000-db93646f6f5fd9ad7992
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-074r-1901000000-8aee95ae3381a4e5fc9d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-9401000000-e1a5c7dba8f4b1f51487
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-181.46217
predicted
DeepCCS 1.0 (2019)
[M+H]+183.82018
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.87321
predicted
DeepCCS 1.0 (2019)

Drug created at October 20, 2016 20:37 / Updated at May 21, 2021 10:22