CAS 90098-04-7|Rebamipide

Introduction：Basic information about CAS 90098-04-7|Rebamipide, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Rebamipide BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Synonyms

Common Name	Rebamipide
CAS Number	90098-04-7	Molecular Weight	370.786
Density	1.4±0.1 g/cm3	Boiling Point	695.0±55.0 °C at 760 mmHg
Molecular Formula	C₁₉H₁₅ClN₂O₄	Melting Point	288-290ºC dec.
MSDS	/	Flash Point	374.1±31.5 °C

Names

Name	Rebamipide
Synonym	More Synonyms

Rebamipide BiologicalActivity

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 ReceptorResearch 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.

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 ReceptorResearch 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.

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
InChIKey	ALLWOAVDORUJLA-UHFFFAOYSA-N
SMILES	O=C(NC(Cc1cc(=O)[nH]c2ccccc12)C(=O)O)c1ccc(Cl)cc1
Storage condition	-20°C Freezer

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

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%

Synonyms

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

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