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MedKoo Cat#: 461192 | Name: Rebamipide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rebamipide is used for mucosal protection, healing of gastroduodenal ulcers, and treatment of gastritis. It works by enhancing mucosal defense, scavenging free radicals,[3] and temporarily activating genes encoding cyclooxygenase-2. Studies have shown that rebamipide can fight the damaging effects of NSAIDs on the GIT mucosa, and more recently, the small intestine, but not for naproxen-induced gastric damage.

Chemical Structure

Rebamipide
Rebamipide
CAS#90098-04-7 (free acid)

Theoretical Analysis

MedKoo Cat#: 461192

Name: Rebamipide

CAS#: 90098-04-7 (free acid)

Chemical Formula: C19H15ClN2O4

Exact Mass: 370.0720

Molecular Weight: 370.79

Elemental Analysis: C, 61.55; H, 4.08; Cl, 9.56; N, 7.56; O, 17.26

Price and Availability

Size Price Availability Quantity
1g USD 230.00
5g USD 440.00
10g USD 710.00
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Related CAS #
111911-87-6 (deleted) 90098-04-7 (free acid) 169809-59-0 (sodium)
Synonym
Mucosta; OPC 12759; OPC-12759; OPC12759; Proamipide; Rebamipide; Rebator;
IUPAC/Chemical Name
2-(4-chlorobenzamido)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propanoic acid
InChi Key
ALLWOAVDORUJLA-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(O)C(NC(C1=CC=C(Cl)C=C1)=O)CC2=CC(NC3=C2C=CC=C3)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Rebamipide increases the levels of prostaglandin E2 (PGE2) and COX-2 in rat gastric mucosa. Rebamipide (30 and 100 mg/kg, i.p.) prevents the formation of gastric ulcers induced by absolute ethanol, sodium hydroxide, or hydrochloric acid in rats. It also increases the production of mucin 16 in stratified corneal epithelial cells in vitro. Formulations containing rebamipide have been used in the treatment of peptic ulcer disease and dry eye disease.
In vitro activity:
Rebamipide induces the differential upregulation of MUC16 in stratified cultures of human corneal epithelial cells, which may have implications to the proper restoration of barrier function in ocular surface disease. Reference: Exp Eye Res. 2016 Dec;153:1-7. https://pubmed.ncbi.nlm.nih.gov/27725198/
In vivo activity:
In a PAS-positve rabbit model, rebamipide increased the number of periodic acid Schiff reagent-positive cells in the conjunctiva, increased the amount of mucin-like substances of the conjunctiva and cornea, and lowered the rose bengal scores in the corneal damage model by desiccation. Rebamipide is a possible candidate drug for treatment of cornea and conjunctival epithelial damage due to its mucin-like substance increasing action. These results indicate that rebamipide could be used in the treatment of dry eye disease. Reference: J Ocul Pharmacol Ther. 2012 Jun;28(3):264-70. https://pubmed.ncbi.nlm.nih.gov/22304618/
Solvent mg/mL mM
Solubility
DMF 1.0 2.70
DMSO 1.0 2.70
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 370.79 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Yasuda-Onozawa Y, Handa O, Naito Y, Ushiroda C, Suyama Y, Toyokawa Y, Murakami T, Yasuda T, Ueda T, Majima A, Hotta Y, Doi T, Tanaka M, Horii Y, Higashimura Y, Mizushima K, Morita M, Uehara Y, Horie H, Fukui A, Dohi O, Okayama T, Yoshida N, Kamada K, Katada K, Uchiyama K, Ishikawa T, Takagi T, Konishi H, Itoh Y. Rebamipide upregulates mucin secretion of intestinal goblet cells via Akt phosphorylation. Mol Med Rep. 2017 Dec;16(6):8216-8222. doi: 10.3892/mmr.2017.7647. Epub 2017 Sep 28. PMID: 28983630. 2. Uchino Y, Woodward AM, Argüeso P. Differential effect of rebamipide on transmembrane mucin biosynthesis in stratified ocular surface epithelial cells. Exp Eye Res. 2016 Dec;153:1-7. doi: 10.1016/j.exer.2016.10.007. Epub 2016 Oct 8. PMID: 27725198. 3. Elwany NE, El Salem A, Mostafa Mohamed N, Khalil SS, Mahmoud NM. Rebamipide protects against experimentally induced intestinal ischemia/reperfusion-promoted liver damage: Impact on SIRT1/β-catenin/FOXO1and NFκB signaling. Int Immunopharmacol. 2023 Jun;119:110269. doi: 10.1016/j.intimp.2023.110269. Epub 2023 May 4. PMID: 37148771. 4. Urashima H, Takeji Y, Okamoto T, Fujisawa S, Shinohara H. Rebamipide increases mucin-like substance contents and periodic acid Schiff reagent-positive cells density in normal rabbits. J Ocul Pharmacol Ther. 2012 Jun;28(3):264-70. doi: 10.1089/jop.2011.0147. Epub 2012 Feb 3. PMID: 22304618.
In vitro protocol:
1. Yasuda-Onozawa Y, Handa O, Naito Y, Ushiroda C, Suyama Y, Toyokawa Y, Murakami T, Yasuda T, Ueda T, Majima A, Hotta Y, Doi T, Tanaka M, Horii Y, Higashimura Y, Mizushima K, Morita M, Uehara Y, Horie H, Fukui A, Dohi O, Okayama T, Yoshida N, Kamada K, Katada K, Uchiyama K, Ishikawa T, Takagi T, Konishi H, Itoh Y. Rebamipide upregulates mucin secretion of intestinal goblet cells via Akt phosphorylation. Mol Med Rep. 2017 Dec;16(6):8216-8222. doi: 10.3892/mmr.2017.7647. Epub 2017 Sep 28. PMID: 28983630. 2. Uchino Y, Woodward AM, Argüeso P. Differential effect of rebamipide on transmembrane mucin biosynthesis in stratified ocular surface epithelial cells. Exp Eye Res. 2016 Dec;153:1-7. doi: 10.1016/j.exer.2016.10.007. Epub 2016 Oct 8. PMID: 27725198.
In vivo protocol:
1. Elwany NE, El Salem A, Mostafa Mohamed N, Khalil SS, Mahmoud NM. Rebamipide protects against experimentally induced intestinal ischemia/reperfusion-promoted liver damage: Impact on SIRT1/β-catenin/FOXO1and NFκB signaling. Int Immunopharmacol. 2023 Jun;119:110269. doi: 10.1016/j.intimp.2023.110269. Epub 2023 May 4. PMID: 37148771. 2. Urashima H, Takeji Y, Okamoto T, Fujisawa S, Shinohara H. Rebamipide increases mucin-like substance contents and periodic acid Schiff reagent-positive cells density in normal rabbits. J Ocul Pharmacol Ther. 2012 Jun;28(3):264-70. doi: 10.1089/jop.2011.0147. Epub 2012 Feb 3. PMID: 22304618.
1: Ballesteros-Sánchez A, Sánchez-González MC, De-Hita-Cantalejo C, Gutiérrez- Sánchez E, Rocha-de-Lossada C, Sánchez-González JM. The Efficacy and Safety of Rebamipide Ophthalmic Suspension (OPC-12759) in Patients with Dry Eye Disease: A Systematic Review of Randomized Controlled Trials. J Clin Med. 2023 Nov 17;12(22):7155. doi: 10.3390/jcm12227155. PMID: 38002767; PMCID: PMC10672675. 2: Kovaleva A, Poluektova E, Maslennikov R, Karchevskaya A, Shifrin O, Kiryukhin A, Tertychnyy A, Kovalev L, Kovaleva M, Lobanova O, Kudryavtseva A, Krasnov G, Fedorova M, Ivashkin V. Effect of Rebamipide on the Intestinal Barrier, Gut Microbiota Structure and Function, and Symptom Severity Associated with Irritable Bowel Syndrome and Functional Dyspepsia Overlap: A Randomized Controlled Trial. J Clin Med. 2023 Sep 20;12(18):6064. doi: 10.3390/jcm12186064. PMID: 37763004; PMCID: PMC10531936. 3: Dai X, Qin B, Zhang H, Zhao H, Zhao H, Huang L, Cheng J, Liu Z, Chen X. Determination of rebamipide in human plasma by a validated liquid chromatography-tandem mass spectrometry: Application in pharmacokinetics research. Pak J Pharm Sci. 2023 Jul;36(4(Special)):1281-1290. PMID: 37606017. 4: Eom Y, Chung SH, Chung TY, Kim JY, Choi CY, Yoon KC, Ko BY, Kim HK, Kim MK, Lee HK, Song JS, Hyon JY, Seo KY, Lee JS, Kim HM. Efficacy and safety of 1% and 2% rebamipide clear solution in dry eye disease: a multicenter randomized trial. BMC Ophthalmol. 2023 Aug 3;23(1):343. doi: 10.1186/s12886-023-03004-1. PMID: 37537533; PMCID: PMC10398964. 5: Bakulina NV, Tikhonov SV, Okovityi SV, Lutaenko EA, Bolshakov AO, Prikhodko VA, Nekrasova AS. [Pharmacokinetics and pharmacodynamics of rebamipide. New possibilities of therapy: A review]. Ter Arkh. 2023 Jan 16;94(12):1431-1437. Russian. doi: 10.26442/00403660.2022.12.202000. PMID: 37167190. 6: Elwany NE, El Salem A, Mostafa Mohamed N, Khalil SS, Mahmoud NM. Rebamipide protects against experimentally induced intestinal ischemia/reperfusion-promoted liver damage: Impact on SIRT1/β-catenin/FOXO1and NFκB signaling. Int Immunopharmacol. 2023 Jun;119:110269. doi: 10.1016/j.intimp.2023.110269. Epub 2023 May 4. PMID: 37148771. 7: Abdel-Fattah MM, Hassanein EHM, Sayed AM, Alsufyani SE, El-Sheikh AAK, Arab HH, Mohamed WR. Targeting SIRT1/FoxO3a/Nrf2 and PI3K/AKT Pathways with Rebamipide Attenuates Acetic Acid-Induced Colitis in Rats. Pharmaceuticals (Basel). 2023 Apr 2;16(4):533. doi: 10.3390/ph16040533. PMID: 37111290; PMCID: PMC10142103. 8: Jain K, Jaju M, Yadav D. Efficacy and safety of topical 2% rebamipide ophthalmic suspension in dry eye disease at tertiary care centre. Indian J Ophthalmol. 2023 Apr;71(4):1598-1602. doi: 10.4103/IJO.IJO_2586_22. PMID: 37026308; PMCID: PMC10276702. 9: Jang DJ, Lee JH, Kim DH, Kim JW, Koo TS, Cho KH. The Development of Super- Saturated Rebamipide Eye Drops for Enhanced Solubility, Stability, Patient Compliance, and Bioavailability. Pharmaceutics. 2023 Mar 15;15(3):950. doi: 10.3390/pharmaceutics15030950. PMID: 36986811; PMCID: PMC10053044. 10: Won YH, Goo YT, Sin GH, Hong SH, Kim CH, Kim MJ, Lee TH, Choi YW. Immediate- release tablet formulation of rebamipide and a pharmacokinetic study in healthy human subjects. Int J Clin Pharmacol Ther. 2023 Jun;61(6):273-288. doi: 10.5414/CP204329. PMID: 36971320. 11: Correction to "Rebamipide potentially mitigates methotrexate-induced nephrotoxicity via inhibition of oxidative stress and inflammation: A molecular and histochemical study". Anat Rec (Hoboken). 2023 Aug;306(8):2208-2209. doi: 10.1002/ar.25184. Epub 2023 Mar 7. Erratum for: Anat Rec (Hoboken). 2021 Mar;304(3):647-661. PMID: 36880452. 12: Hasan S, Perween N, Saeed S, Kaur M, Gombra V, Rai A. Evaluation of 5% Amlexenox Oral Paste and Rebamipide Tablets in Treatment of Recurrent Apthous Stomatitis and Comparison with Dologel CT. Indian J Otolaryngol Head Neck Surg. 2022 Dec;74(Suppl 3):5228-5234. doi: 10.1007/s12070-020-01858-1. Epub 2020 Apr 27. PMID: 36742475; PMCID: PMC9895324. 13: Bae S, Huh KY, Oh J, Yu KS, Kim A. Evaluation of Safety, Tolerability and Pharmacokinetic Characteristics of SA001 and Its Active Metabolite Rebamipide after Single and Multiple Oral Administration. Pharmaceuticals (Basel). 2023 Jan 16;16(1):132. doi: 10.3390/ph16010132. PMID: 36678630; PMCID: PMC9862565. 14: Jhun J, Moon J, Kim SY, Cho KH, Na HS, Choi J, Jung YJ, Song KY, Min JK, Cho ML. Rebamipide treatment ameliorates obesity phenotype by regulation of immune cells and adipocytes. PLoS One. 2022 Dec 27;17(12):e0277692. doi: 10.1371/journal.pone.0277692. PMID: 36574392; PMCID: PMC9794058. 15: Jia RJ, Wang XP, Zhang ZH, Cui HH, Qin R, Du DY, Liu Y. Effect of Rabeprazole and Rebamipide in the Treatment of Upper Gastrointestinal Hemorrhage Associated with Dual Antiplatelet Therapy in Elderly Patients with Coronary Heart Disease. Clin Appl Thromb Hemost. 2022 Jan-Dec;28:10760296221130746. doi: 10.1177/10760296221130746. PMID: 36411982; PMCID: PMC9703470. 16: Oh DJ, Yoon H, Kim HS, Choi YJ, Shin CM, Park YS, Kim N, Lee DH, Ha YJ, Kang EH, Lee YJ, Kim N, Kim KJ, Liu F. The effect of rebamipide on non-steroidal anti-inflammatory drug-induced gastro-enteropathy: a multi-center, randomized pilot study. Korean J Intern Med. 2022 Nov;37(6):1153-1166. doi: 10.3904/kjim.2021.216. Epub 2022 Nov 1. PMID: 36375487; PMCID: PMC9666262. 17: Corrigendum to 'Rebamipide suppresses TNF-α; mediated inflammation in vitro and attenuates the severity of dermatitis in mice'. FEBS J. 2023 Mar;290(6):1663-1664. doi: 10.1111/febs.16654. Epub 2022 Oct 26. Erratum for: FEBS J. 2015 Jun;282(12):2317-26. PMID: 36288791. 18: Zaky HS, Abdel-Sattar SA, Allam A, Ahmed HI. Further insights into the impact of rebamipide on gentamicin-induced nephrotoxicity in rats: modulation of SIRT1 and β-catenin/cyclin D1 pathways. Drug Chem Toxicol. 2023 Nov;46(5):851-863. doi: 10.1080/01480545.2022.2104867. Epub 2022 Jul 28. PMID: 35899710. 19: Teshigawara T, Meguro A, Mizuki N. Impact of Perioperative Dry Eye Treatment with Rebamipide Versus Artificial Tears on Visual Outcomes After Cataract Surgery in Japanese Population. Ophthalmol Ther. 2022 Aug;11(4):1479-1491. doi: 10.1007/s40123-022-00523-w. Epub 2022 May 19. PMID: 35588046; PMCID: PMC9253222. 20: Jang E, Park M, Jeong JE, Lee JY, Kim MG. Frequently reported adverse events of rebamipide compared to other drugs for peptic ulcer and gastroesophageal reflux disease. Sci Rep. 2022 May 12;12(1):7839. doi: 10.1038/s41598-022-11505-0. PMID: 35552457; PMCID: PMC9098635.