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]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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
DrugBank ID: DB11656
TTD ID: D03BQP
INTEDE ID: DR1399

Combinatorial Drugs (CBD)

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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]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[4]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.