REBAMIPIDE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H15ClN2O4
Molecular Weight	370.786
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

OC(=O)C(CC1=CC(=O)NC2=C1C=CC=C2)NC(=O)C3=CC=C(Cl)C=C3

InChI

InChIKey=ALLWOAVDORUJLA-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description

Rebamipide, an amino acid derivative of 2-(1H)-quinolinone, is used for mucosal protection, healing of gastroduodenal ulcers, and treatment of gastritis. It works by enhancing mucosal defense, scavenging free radicals, and temporarily activating genes encoding cyclooxygenase-2. Rebamipide is used in a number of Asian countries including Japan (marketed as Mucosta), South Korea, China, and India (where it is marketed under the trade name Rebagen). It is not approved by the Food and Drug Administration for use in the United States. Studies have shown that rebamipide can fight the damaging effects of NSAIDs on the GIT mucosa.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
AMP-activated protein kinase, AMPK 17	Activator 1,447

Conditions

Condition	Modality	Highest Phase	Product
Peptic ulcer 72	Primary	Approved 8,583	Mucosta
Gastritis 46	Primary	Approved 8,583	Mucosta
Gastropathy 2	Primary	Phase IV 63	Mucosta

C_max

Value	Dose	Analyte	Population
0.96 ng/mL	2 drop single, ocular	REBAMIPIDE plasma	Homo sapiens
1 ng/mL	2 drop single, ocular	REBAMIPIDE plasma	Homo sapiens
0.79 ng/mL	2 drop single, ocular	REBAMIPIDE plasma	Homo sapiens
2.18 ng/mL	2 drop 4 times / day multiple, ocular	REBAMIPIDE plasma	Homo sapiens
1.66 ng/mL	2 drop 4 times / day multiple, ocular	REBAMIPIDE plasma	Homo sapiens
2.13 ng/mL	2 drop 4 times / day multiple, ocular	REBAMIPIDE plasma	Homo sapiens
4.39 ng/mL	2 drop 4 times / day multiple, ocular	REBAMIPIDE plasma	Homo sapiens
2.19 ng/mL	2 drop 4 times / day multiple, ocular	REBAMIPIDE plasma	Homo sapiens
218.12 ng/mL	100 mg single, oral	REBAMIPIDE serum	Homo sapiens

AUC

Value	Dose	Analyte	Population
5.45 ng × h/mL	2 drop single, ocular	REBAMIPIDE plasma	Homo sapiens
4.71 ng × h/mL	2 drop single, ocular	REBAMIPIDE plasma	Homo sapiens
5.55 ng × h/mL	2 drop single, ocular	REBAMIPIDE plasma	Homo sapiens
10.3 ng × h/mL	2 drop 4 times / day multiple, ocular	REBAMIPIDE plasma	Homo sapiens
13.48 ng × h/mL	2 drop 4 times / day multiple, ocular	REBAMIPIDE plasma	Homo sapiens
851.68 ng × h/mL	100 mg single, oral	REBAMIPIDE serum	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
10.26 h	2 drop single, ocular	REBAMIPIDE plasma	Homo sapiens
5.64 h	2 drop single, ocular	REBAMIPIDE plasma	Homo sapiens
11.34 h	2 drop single, ocular	REBAMIPIDE plasma	Homo sapiens
5.19 h	2 drop 4 times / day multiple, ocular	REBAMIPIDE plasma	Homo sapiens
10.64 h	2 drop 4 times / day multiple, ocular	REBAMIPIDE plasma	Homo sapiens
1.96 h	100 mg single, oral	REBAMIPIDE serum	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
1.4%			REBAMIPIDE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
200 mg 3 times / day multiple, oral Higher than recommended	unhealthy, ADULT
100 mg 3 times / day multiple, oral Recommended	unhealthy, ADULT	Disc. AE: Dizziness...
150 mg 2 times / day multiple, oral Studied dose	unhealthy, ADULT

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AEs

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AE	Significance	Dose	Population
Dizziness	grade 1, 0.44% Disc. AE	100 mg 3 times / day multiple, oral Recommended	unhealthy, ADULT

Showing 1 to 1 of 1 entries

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252 activator 150 substrate 1,946 inducer 1,087	inhibitor 2,438	inhibitor 2,507	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B3 961 CYP2A6 879 OATP1B1 1,079 CYP19A1 429 CYP1A2 2,153 CYP2C19 2,057 CYP2E1 1,060	MRP 9 P-gp 2,052 BCRP 697

Drug as perpetrator

Show entries

Target	Modality	Activity
CYP2A6 911	inhibitor 4,027	no [IC50 6800 uM]
CYP1A2 2,333	inhibitor 4,027	no [Inhibition 50 uM]
CYP2C19 2,141	inhibitor 4,027	no [Inhibition 50 uM]
CYP2C9 2,497	inhibitor 4,027	no [Inhibition 50 uM]
CYP2D6 2,546	inhibitor 4,027	no [Inhibition 50 uM]

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Drug as victim

Show entries

Target	Modality	Activity
BCRP 697	substrate 4,014	no
CYP3A4 1,946	substrate 4,014	yes [Km 1010 uM]
MRP 9	substrate 4,014	yes
P-gp 2,052	substrate 4,014	yes

Showing 1 to 4 of 4 entries

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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PubMed

Show entries

Title	Date	PubMed
Effect of rebamipide on prostaglandin EP4 receptor gene expression in rat gastric mucosa.	2000 Jul	10882227
Alterations of epithelial permeability by Helicobacter and IL-1beta in vitro: protective effect of rebamipide.	2001 Jul	11478510
Effects of anti-ulcer agents on ethanol-induced gastric mucosal lesions in D-galactosamine-induced hepatitis rats.	2002	12236047
Involvement of cytochrome P450 in the metabolism of rebamipide by the human liver.	2002 Jul	12162853
Preoperative administration of rebamipide significantly lowers body temperature and circulating interleukin-6 in gastric cancer patients after gastrectomy.	2003	14506330

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Patents

Sample Use Guides

In Vivo Use Guide

100 mg tid, in the morning, evening and before bedtime.

Route of Administration: Oral

In Vitro Use Guide

Human gastric carcinoma AGS cells were treated with rebamipide at 0.1-5mkM for 2 h. Cells were lysed followed by western blot analysis. The blots were probed with an anti-p-AMPKalpha antibody specific for threonine 172-phosphorylated AMPKalpha.

Show entries

Name

Type

Language

REBAMIPIDE

Official Name

English

MUCOSTA

Preferred Name

English

REBAMIPIDE [MI]

Common Name

English

REBATOR

Brand Name

English

(±)-.ALPHA.-(P-CHLOROBENZAMIDO)-1,2-DIHYDRO-2-OXO-4-QUINOLINEPROPIONIC ACID

Common Name

English

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Show entries

Classification Tree

Code System

Code

Other drugs for peptic ulcer and gastro-oesophageal reflux disease (GORD)

WHO-ATC

A02BX14

Agent Affecting Digestive System or Metabolism

NCI_THESAURUS

C29701

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Show entries

Code System

Code

Type

Description

IUPHAR

871

PRIMARY

FDA UNII

LR583V32ZR

PRIMARY

CAS

90098-04-7

PRIMARY

EPA CompTox

DTXSID8045937

PRIMARY

NCI_THESAURUS

C29852

PRIMARY

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ACTIVE MOIETY


					LR583V32ZR

REBAMIPIDE

PARENT (METABOLITE ACTIVE)


					1L45T26ZFA

REBAMIPIDE MOFETIL

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator