Details of the Drug

General Information of Drug (ID: DM2GHCR)

Drug Name
Rebamipide
Synonyms
rebamipide; 90098-04-7; Mucosta; Proamipide; 111911-87-6; OPC-12759; Rebamipidum; Pramipide; Rebamipide [INN:JAN]; Rebamipidum [INN-Latin]; Rebamipida [INN-Spanish]; OPC 12759; CCRIS 3585; Rebamipide hydrate; 2-(4-Chlorobenzoylamino)-3-(1,2-dihydro-2-oxo-4-quinolyl)propionic acid; 139344-42-6; 2-[(4-chlorobenzoyl)amino]-3-(2-oxo-1H-quinolin-4-yl)propanoic acid; Mucosta hydrate; NCGC00095161-01; Proamipide hydrate; 2-(4-Chlorobenzamido)-3-[2(1H)-quinolinon-4-yl]propionic Acid
Indication
Disease Entry ICD 11 Status REF
Peptic ulcer DA61 Phase 3 [1]
ATC Code
A02BX14: Rebamipide
A02BX: Other drugs for peptic ulcer and gastro-oesophageal reflux disease (GORD)
A02B: DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
A02: DRUGS FOR ACID RELATED DISORDERS
A: ALIMENTARY TRACT AND METABOLISM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 370.8
Logarithm of the Partition Coefficient (xlogp) 2.4
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [2]
Chemical Identifiers
Formula
C19H15ClN2O4
IUPAC Name
2-[(4-chlorobenzoyl)amino]-3-(2-oxo-1H-quinolin-4-yl)propanoic acid
Canonical SMILES
C1=CC=C2C(=C1)C(=CC(=O)N2)CC(C(=O)O)NC(=O)C3=CC=C(C=C3)Cl
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)
InChIKey
ALLWOAVDORUJLA-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5042
ChEBI ID
CHEBI:93814
CAS Number
90098-04-7
UNII
LR583V32ZR
DrugBank ID
DB11656
TTD ID
D03BQP
INTEDE ID
DR1399
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
N-formyl peptide receptor (FPR1) TT5Y4EM FPR1_HUMAN Antagonist [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [5]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [5]
ATP-binding cassette sub-family C member 4 (ABCC4) OTO27PAL MRP4_HUMAN Regulation of Drug Effects [6]
Aurora kinase B (AURKB) OTIY4VHU AURKB_HUMAN Gene/Protein Processing [7]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [7]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [5]
Bcl-2-like protein 11 (BCL2L11) OTNQQWFJ B2L11_HUMAN Gene/Protein Processing [5]
E3 ubiquitin-protein ligase XIAP OT24GP9B XIAP_HUMAN Gene/Protein Processing [5]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [8]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 871).
2 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3 Rebamipide suppresses formyl-methionyl-leucyl-phenylalanine (fMLP)-induced superoxide production by inhibiting fMLP-receptor binding in human neutrophils. J Pharmacol Exp Ther. 2001 Apr;297(1):388-94.
4 Involvement of cytochrome P450 in the metabolism of rebamipide by the human liver. Xenobiotica. 2002 Jul;32(7):573-86.
5 Rebamipide suppresses 5-fluorouracil-induced cell death via the activation of Akt/mTOR pathway and regulates the expression of Bcl-2 family proteins. Toxicol In Vitro. 2018 Feb;46:284-293. doi: 10.1016/j.tiv.2017.10.019. Epub 2017 Oct 17.
6 Multichannel liquid chromatography-tandem mass spectrometry cocktail method for comprehensive substrate characterization of multidrug resistance-associated protein 4 transporter. Pharm Res. 2007 Dec;24(12):2281-96.
7 Rebamipide inhibits gastric cancer growth by targeting survivin and Aurora-B. Biochem Biophys Res Commun. 2005 Aug 19;334(1):207-12. doi: 10.1016/j.bbrc.2005.05.204.
8 Management of recurrence of symptoms of gastroesophageal reflux disease: synergistic effect of rebamipide with 15 mg lansoprazole. Dig Dis Sci. 2010 Dec;55(12):3393-8. doi: 10.1007/s10620-010-1166-9. Epub 2010 Mar 3.