Description Pharmacological effects Pharmacokinetics synthetic route Indications Dosage side effects Safety Side effects Chemical Properties Uses
ChemicalBook > CAS DataBase List > Rebamipide

Rebamipide

Description Pharmacological effects Pharmacokinetics synthetic route Indications Dosage side effects Safety Side effects Chemical Properties Uses
Rebamipide Structure
Rebamipide
  • CAS No.90098-04-7
  • Chemical Name:Rebamipide
  • CBNumber:CB5700987
  • Molecular Formula:C19H15ClN2O4
  • Formula Weight:370.79
  • MOL File:90098-04-7.mol
Rebamipide Property
  • Melting point: :288-290°C dec.
  • Boiling point: :695.0±55.0 °C(Predicted)
  • Density  :1.394±0.06 g/cm3(Predicted)
  • storage temp.  :-20°C Freezer
  • solubility  :DMSO: >5mg/mL
  • pka :3.38±0.10(Predicted)
  • form  :powder
  • color  :white
  • Merck  :14,8124
  • InChIKey :ALLWOAVDORUJLA-UHFFFAOYSA-N
  • CAS DataBase Reference :90098-04-7(CAS DataBase Reference)
  • FDA UNII :LR583V32ZR
Safety
  • RIDADR  :UN 2811 6.1 / PGIII
  • WGK Germany  :3
  • RTECS  :VC2518500
  • HS Code  :29337900
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H301
  • Precautionary statements P301+P310
Rebamipide Price More Price(9)
  • Brand: Sigma-Aldrich
  • Product number: R5655
  • Product name : Rebamipide hydrate
  • Purity: ≥98% (HPLC), powder
  • Packaging: 5mg
  • Price: $64.4
  • Updated: 2018/11/13
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: R5655
  • Product name : Rebamipide hydrate
  • Purity: ≥98% (HPLC), powder
  • Packaging: 25mg
  • Price: $257
  • Updated: 2018/11/13
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: R0085
  • Product name : Rebamipide
  • Purity: >98.0%(HPLC)
  • Packaging: 1g
  • Price: $79
  • Updated: 2020/06/24
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: R0085
  • Product name : Rebamipide
  • Purity: >98.0%(HPLC)
  • Packaging: 5g
  • Price: $234
  • Updated: 2020/06/24
  • Buy: Buy
  • Brand: Cayman Chemical
  • Product number: 17186
  • Product name : Rebamipide
  • Purity:  ≥98%
  • Packaging: 5g
  • Price: $145
  • Updated: 2020/06/24
  • Buy: Buy

Rebamipide Chemical Properties,Usage,Production

  • Description Rebamipide is a quinolinone derivative that stimulates endogenous PGE2 generation in gastric mucosa, enhancing gastric mucosal defense in a COX-2-dependent manner.
    Rebamipide has been shown to inhibit the production of reactive oxygen species and to decrease cytokine release induced by H. pylori infection.
    A daily oral dose of 100 mg/kg was found to be protective against the development of pyloric channel ulcers in Mongolian gerbils infected with H. pylori.
    In addition to the stomach, rebamipide can also enhance secretion of mucin covering the conjunctiva and cornea, which is important for tear film adhesion.
    Rebamipide, a gastroprotective drug, was developed in Japan and was proven to be superior to cetraxate, the former most prescribed drug of the same category, in 1989 in the treatment for gastric ulcers. The initially discovered basic mechanisms of action of rebamipide included its action as a prostaglandin inducer and oxygen free-radical scavenger. In the last 5 years, several basic and clinical studies have been performed for functional dyspepsia, chronic gastritis, NSAID-induced gastrointestinal injuries, gastric ulcer following eradication therapy for Helicobacter pylori, gastric ulcer after endoscopic surgery and ulcerative colitis. In addition, several molecules have been identified as therapeutic targets of rebamipide to explain its pleiotropic pharmacological actions.
  • Pharmacological effects The chemical structure of rebamipide contains the para-amide groups in the benzyl group, the carbonyl group in 2’ position, and the double bond in 3’, 4’ position. It has a dose-dependent inhibitory effect on the reactive oxygen species produced by the activation of neutrophils and can further effectively scavenger free radicals, thereby preventing the damage of free radical on the gastric mucosa. This product can also promote gastric prostaglandin synthesis, enhance gastric mucosal barrier. In addition, by preventing the adhesion of Helicobacter pylori (Hp) adhesion to gastric epithelial cells, the product can reduce oxidative stress, reduce the concentration of cell factor produced by H. pylori and further inhibiting of HP’s injury on gastric mucosa.
    Animal experiment has already showed that rebamipide can remove free radicals within the epithelial cells, and have a significant inhibition on the O2-produced by neutrophils; it also has some effects on eliminating hydroxyl radical; it can also inhibit HP and its production of chemotaxis factors. It can also inhibit the injury of gastric mucosa caused by bile acid and increase the synthesis of prostaglandins.
    The above information is edited by the chemicalbook of Dai Xiongfeng.
  • Pharmacokinetics Absorption and Metabolism: After oral administration of 0.6g, the time for reaching peak of plasma concentration is (1.95 ± 0.73) h, the peak plasma concentration is (510.3 ± 152.0) ng/ml, its elimination half-life is (1.75 ± 0.63) hours. According to reports, after oral administration of 0.1 g of rebamipide 0.1g, after about two hours, the plasma concentration reaches peak at 210ng/ml with the elimination half-life of about 2 hours; about 10% of the dose is excreted through the urine. Multiple dose study has showed that the drug did not accumulate in the human body.
  • synthetic route The synthetic route of Rebamipide
    Figure 2 The synthetic route of Rebamipide.
  • Indications 1. Prevents and treatment of injury of gastric mucosal caused by NSAIDs
    Rebamipide has an obvious reversal effect on the side effects of NSAIDs drug-induced reduction of the synthesis of gastric mucosal prostaglandin and increased permeability of mucosa. Further study has found that patients taking NSAIDs had gotten high expression of gastric epithelial HIF-1, suggesting that the gastric mucosa of patients is within hypoxic-ischemic state; However, patients taking rebamipide has significantly reduced HIF-1 expression, demonstrating that rebamipide has a very good protective effect on the gastric mucosa of patients taking NSAIDs table. From this perspective, rebamipide may have a prevention and treatment effect on NSAIDs (especially non-selective NSAIDs) induced gastric mucosal damage.
    2. HP-related gastritis treatment
    Haruma et al have reported that: in the observation of clinical treatment of 86 HP-positive patients, 53 patients taking rebamipide had stomach antrum and stomach body monocytes with significant reduction on granulocytes cell infiltration and had the stomach inflammation much more be alleviated than those without medication, indicating that it has a high-quality effect on treating HP-associated gastritis.
    3. Other
    Studies have reported that patients with gastric cancer who have taken rebamipide before surgeries had significant lower body temperature than the control group at 3 days after surgeries. Moreover, their serum IL-6 levels are also significantly lower than the control group, demonstrating that rebamipide has alleviated effect on the post-surgery systemic inflammatory response syndrome of gastric cancer patients; rebamipide may also become a new means of treatment for ulcerative colitis; may also become a new and effective approach for treating Meniere's disease.
  • Dosage The adult dosage of rebamipide is 100 mg orally three times daily.
    RAU: 3 tablets/day for 7-14 days.
    Behcet's disease: 3 tablets/day for 2 months.
  • side effects The most commonly reported Rebamipide side effects:
       Pyrexia (4)
       Pleural Effusion (4)
       Renal Failure Acute (4)
       Liver Disorder (4)
       Nausea (4)
       Pancytopenia (3)
       Dyspnoea (3)
       Diarrhoea (3)
       Hypokalaemia (3)
       Malaise (3)
       Renal Impairment (3)
       Decreased Appetite (3)
       Transitional Cell Carcinoma (2)
       Constipation (2)
       Urticaria (2)
       Pruritus (2)
       Vomiting (2)
       Feeling Abnormal (2)
       Blood Glucose Increased (2)
       Blood Pressure Decreased (2)
    Hypersensitivity and rash was seen in less than 1% of patients.
  • Safety Rebamipide promotes the ulcer healing rate to be as high as 56% to 67%, higher than other gastric mucosal protective agent; it can increase the eradication frequency without the increase of antibiotics, preventing phenomenon of the increase of adverse reactions caused by increased dose of antibiotics.
  • Side effects Adverse reactions include leukopenia, thrombocytopenia, dizziness, drowsiness, numbness, abnormal taste, bloating, constipation, thirst, nausea, vomiting, heartburn, belching, abdominal pain, diarrhea, throat foreign body sensation, increased blood urea nitrogen, swollen breasts galactorrhea, menstrual disorders and eczema. It may also cause male breast enlargement. It can also occasionally cause coughing, difficulty in breathing, palpitations, fever, swelling, rash, itching and liver dysfunction. During the medication, if allergic reactions such as itching, rashes or eczema occurs, stop taking drugs immediately. The incidence is about 2.2% with the symptoms disappearing after withdrawal. Disable it for people who are allergic to this drug. The elderly and pregnant women should take with caution. Lactating women should stop breastfeeding upon medication. Safety of children's medication safety is still unclear.
  • Chemical Properties obtain the white powder from dimethylformamide-water with its hemihydrate m.p. being 288-290°C (decomposition).
    (-)-Configuration: from dimethylformamide to give colorless needles, mp 305~306 °C (decomposition). [α] D20-116.7 ° (C = 1.0, dimethylformamide).
    (+)-Configuration: from dimethylformamide to give colorless needles, mp 305~306 °C (decomposition). [α] D20 + 116.9 ° (C = 1.0, dimethylformamide).
  • Uses It is used for treating stomach ulcers.
    It is a kind of novel anti-ulcer drugs.
  • Chemical Properties White Powder
  • Uses Shows antiulcer activity in rats
  • Uses antiulcer, antioxidant
  • Uses An inducer of endogenous prostaglandin and a oxygen-derived free radical scavenger.
Rebamipide Preparation Products And Raw materials
Raw materials
Preparation Products
Global(268)Suppliers
  • Supplier:
    Henan Tianfu Chemical Co.,Ltd.
  • Tel:0371-55170693
  • Fax:0371-55170693
  • Email:info@tianfuchem.com
  • Country:CHINA
  • ProdList:22622
  • Advantage:55
  • Supplier:
    Shanghai Time Chemicals CO., Ltd.
  • Tel:+8618017249410 +86-021-57951555
  • Fax:+86-021-57951555
  • Email:jack.li@time-chemicals.com
  • Country:CHINA
  • ProdList:1365
  • Advantage:55
  • Supplier:
    career henan chemical co
  • Tel:+86-371-86658258
  • Fax:
  • Email:sales@coreychem.com
  • Country:CHINA
  • ProdList:30025
  • Advantage:58
  • Supplier:
    Accela ChemBio Inc.
  • Tel:(+1)-858-699-3322
  • Fax:(+1)-858-876-1948
  • Email:info@accelachem.com
  • Country:United States
  • ProdList:19969
  • Advantage:58
  • Supplier:
    Zhonglan Industry Co., Ltd.
  • Tel:(86) 531-82956570
  • Fax:(86) 531-82956571
  • Email:sales@zhonglanindustry.com
  • Country:CHINA
  • ProdList:4895
  • Advantage:58
  • Supplier:
    QUALITY CONTROL CHEMICALS INC.
  • Tel:(323) 306-3136
  • Fax:(626) 453-0409
  • Email:orders@qcchemical.com
  • Country:United States
  • ProdList:8406
  • Advantage:58
  • Supplier:
    Xiamen AmoyChem Co., Ltd
  • Tel:+86 592-605 1114
  • Fax:
  • Email:sales@amoychem.com
  • Country:CHINA
  • ProdList:6371
  • Advantage:58
  • Supplier:
    BOC Sciences
  • Tel:1-631-619-7922 1-631-619-7922
  • Fax:1-631-614-7828
  • Email:inquiry@bocsci.com
  • Country:United States
  • ProdList:20039
  • Advantage:58
90098-04-7, RebamipideRelated Search:
  • (+-)-1,2-dihydro-alpha-((4-chlorobenzoyl)amino)-2-oxo-4-quinolinepropanoica
  • (+-)-2-(4-chlorobenzoylamino)-3-(2(1h)-quinolinon-4-yl)propionicacid
  • Mucosta
  • Proamipide
  • 2-dihydro-alpha-((4-chlorobenzoyl)amino)-2-oxo- (+-)-4-quinolinepropanoic 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
  • OPC-12759, Mucosta, α-[(4-Chlorobenzoyl)-amino]-1,2-dihydro-2-oxo-4-quinolinepropanoic Acid
  • 2-(4-Chlorobenzoylamino)-3-(1,2-dihydro-2-oxo-4-
  • (+-)-1,2-Dihydro-alpha-((4-chlorobenzoyl)amino)-2-oxo-4-quinolinepropanoic acid
  • 4-Quinolinepropanoic acid, 1,2-dihydro-alpha-((4-chlorobenzoyl)amino)-2-oxo-, (+-)
  • 2-(4-Chlorobenzoylamino)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propionic acid
  • α-[(4-Chlorobenzoyl)amino]-1,2-dihydro-2-oxo-4-quinolinepropanoic acid
  • 2-[(4-chlorobenzoyl)amino]-3-(2-keto-1H-quinolin-4-yl)propionic acid
  • 2-[(4-chlorobenzoyl)amino]-3-(2-oxo-1H-quinolin-4-yl)propanoic acid
  • 2-[(4-chlorophenyl)carbonylamino]-3-(2-oxo-1H-quinolin-4-yl)propanoic acid
  • Korea-FDA API
  • 2-(4-Chlorobenzamido)-3-[2(1H)-quinolinon-4-yl]propionic Acid
  • Mucosta hydrate
  • α-[(4-Chlorobenzoyl)amino]-1,2-dihydro-2-oxo-4-quinolinepmpanoic acid
  • 0PC-12759
  • (111911-87-6) rebamipide
  • REBAMIPIDE
  • REBAPIMIDE
  • REBAMIPIDE,99.5%
  • RebamipideRebamipide
  • 4-Quinolinepropanoic acid, a-[(4-chlorobenzoyl)amino]-1,2-dihydro-2-oxo- (9CI)
  • OPC 12759 hydrate
  • Proamipide hydrate
  • Rebamipide hydrate
  • α-[(4-Chlorobenzoyl)amino]-1,2-dihydro-2-oxo-4-quinolinepropanoic acid hydrate
  • OPC-12759, Mucosta, a-[(4-Chlorobenzoyl)-amino]-1,2-dihydro-2-oxo-4-quinolinepropanoic Acid
  • Rebagen
  • Rebamipide, 99%, Inducer of endogenous prostaglandin and a oxygen-derived free radical scavenger
  • 1,2-dihydro-alpha-((4-chlorobenzoyl)amino)-2-oxo-4-quinolinepropanoicaci(
  • 2-dihydro-alpha-((4-chlorobenzoyl)amino)-2-oxo-(+-)-4-quinolinepropanoicaci
  • opc12759
  • opc-12759
  • Rebamipid
  • Rebamipide &gt
  • 4-Quinolinepropanoic acid, α-[(4-chlorobenzoyl)amino]-1,2-dihydro-2-oxo-
  • 4-Quinolinepropanoic acid, α-[(4-chlorobenzoyl)amino]-1,2-dihydro-2-oxo-
  • 90098-04-7
  • 90089-04-7
  • 11911-90-1
  • C19H15ClN2O4
  • Antiulcerative
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • API's
  • Active Pharmaceutical Ingredients
  • Amino Acid Derivatives