Rebamipide

Names

[ Name ]:
Rebamipide

[Synonym ]:
1H-benzimidazol-2-yl(4-chlorophenyl)methanone
2-(4-chlorobenzoylamino)-3-[2(1H)-quinolinone-4-yl]propionic acid
4-quinolinepropanoic acid, α-[(4-chlorobenzoyl)amino]-2-hydroxy-
Mucosta
Proamipide
2-(4-Chlorobenzoylamino)-3-[2(1H)-quinolinon-4-yl]propionic acid
2-(4-Chlorobenzoylamino)-3-(1,2-dihydro-2-oxo-4-quinolyl)propionic acid
2-(4-chlorobenzamido)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propanoic acid
REBAMIPIDEREBAMIPIDE
(R)-2-(4-chlorobenzamido)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propanoic acid
N-(4-Chlorobenzoyl)-3-(2-hydroxyquinolin-4-yl)alanine
N-(4-Chlorobenzoyl)-3-(2-oxo-1,2-dihydro-4-quinolinyl)alanine
REACTIVE ORANGE 122,CINO.ORANGE 122
(±)-a-(p-Chlorobenzamido)-1,2-dihydro-2-oxo-4-quinolinepropionic acid
N-[(4-chlorophenyl)carbonyl]-3-(2-oxo-1,2-dihydroquinolin-4-yl)alanine
MFCD00866895
N-(4-Chlorobenzoyl)-3-(2-oxo-1,2-dihydroquinolin-4-yl)alanine
2-[(4-chlorobenzoyl)amino]-3-(2-oxo-1H-quinolin-4-yl)propanoic acid
2-(4-chlorobenzoyl)benzimidazole
Rebamipide
2-(4-chlorobenzoylamino)-3-[2(1H)-quinolon-4-yl]propionic acid
4-Quinolinepropanoic acid, α-[(4-chlorobenzoyl)amino]-1,2-dihydro-2-oxo-
a-[(4-Chlorobenzoyl)amino]-1,2-dihydro-2-oxo-4-quinolinepropanoic acid

Biological Activity

[Description]:

Rebamipide is an inducer of endogenous prostaglandin and a oxygen-derived free radical scavenger.Target: OthersRebamipide is the first anti-gastric ulcer and antigastritis drug that not only increases endogenous prostaglandin in gastric mucosa but also scavenges oxygen-derived free radicals and inhibits their production. The inhibitory effect of rebamipide on lipid peroxidation induced by a free radical initiator was also demonstrated by the in vitro system using rat gastric mucosal homogenates. These data indicate that rebamipide offers a potential for protection against reactive oxygen- and activated neutrophil-associated gastric mucosal injury by scavenging hydroxyl radical and inhibiting neutrophil activation or lipid peroxidation [1]. Rebamipide can contribute to the management of patients who are taking NSAIDs or are infected with H. pylori. Rebamipide may enhance eradication of H. pylori-infection using standard eradication therapy [2]. Rebamipide is beneficial for obtaining a better quality of ulcer healing and reduction of future ulcer relapse [3].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Prostaglandin Receptor

Research Areas >> Metabolic Disease

[References]

[1]. Iinuma, S., et al., In vitro studies indicating antioxidative properties of rebamipide. Dig Dis Sci, 1998. 43(9 Suppl): p. 35S-39S.

[2]. Arakawa, T., et al., Rebamipide: overview of its mechanisms of action and efficacy in mucosal protection and ulcer healing. Dig Dis Sci, 1998. 43(9 Suppl): p. 5S-13S.

[3]. Arakawa, T., et al., Rebamipide, novel prostaglandin-inducer accelerates healing and reduces relapse of acetic acid-induced rat gastric ulcer. Comparison with cimetidine. Dig Dis Sci, 1995. 40(11): p. 2469-72.

[Related Small Molecules]

Dinoprostone | Prostaglandin E1 | E7046 | ONO-AE3-208 | PF 04418948 | Fevipiprant | grapiprant | TG6-10-1 | Taprenepag | GW 627368 | MRE-269 | Ramatroban | AH 6809 | Laropiprant | AZD1981

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
695.0±55.0 °C at 760 mmHg

[ Melting Point ]:
288-290ºC dec.

[ Molecular Formula ]:
C₁₉H₁₅ClN₂O₄

[ Molecular Weight ]:
370.786

[ Flash Point ]:
374.1±31.5 °C

[ Exact Mass ]:
370.072021

[ PSA ]:
99.26000

[ LogP ]:
2.90

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.634

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VC2518500

CHEMICAL NAME :: 4-Quinolinepropanoic acid, 1,2-dihydro-alpha-((4-chlorobenzoyl)amino)-2-oxo-, (+-)-

CAS REGISTRY NUMBER :: 90098-04-7

LAST UPDATED :: 199112

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C19-H15-Cl-N2-O4

MOLECULAR WEIGHT :: 370.81

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 20,362,1989

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4 gm/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 20,362,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 700 mg/kg

TOXIC EFFECTS :: Kidney, Ureter, Bladder - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 20,362,1989

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Kidney, Ureter, Bladder - other changes

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 20,362,1989

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 20,362,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2637 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory depression Kidney, Ureter, Bladder - other changes Skin and Appendages - hair

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 20,362,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 572 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Kidney, Ureter, Bladder - other changes

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 20,362,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1353 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - effect, not otherwise specified Lungs, Thorax, or Respiration - respiratory depression Blood - changes in spleen

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 20,362,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 20,362,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 20,362,1989 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 26 gm/kg

SEX/DURATION :: female 17-21 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 20,478,1989

Safety Information

[ HS Code ]:
2933790090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933499090

[ Summary ]:
2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Related Compounds

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