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MedKoo Cat#: 464113 | Name: Rebamipide-d4
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Description:

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

Rebamipide-d4 is intended for use as an internal standard for the quantification of rebamipide by GC- or LC-MS. Rebamipide is a gastroprotective agent and mucin secretagogue.

Chemical Structure

Rebamipide-d4
Rebamipide-d4
CAS#1219409-06-9

Theoretical Analysis

MedKoo Cat#: 464113

Name: Rebamipide-d4

CAS#: 1219409-06-9

Chemical Formula: C19H11D4ClN2O4

Exact Mass: 374.0971

Molecular Weight: 374.81

Elemental Analysis: C, 60.89; H, 5.11; Cl, 9.46; N, 7.47; O, 17.07

Price and Availability

Size Price Availability Quantity
1mg USD 500.00 2 Weeks
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Related CAS #
90098-04-7
Synonym
Rebamipide-d4; Rebamipide d4;
IUPAC/Chemical Name
2-(4-chlorobenzamido-2,3,5,6-d4-2,3,5,6-d4)-3-(2-oxo-1,2-dihydroquinolin-4-yl)propanoic acid
InChi Key
ALLWOAVDORUJLA-KDWZCNHSSA-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)/i5D,6D,7D,8D
SMILES Code
O=C(NC(CC(C1=CC=CC=C1N2)=CC2=O)C(O)=O)C3=C(C([2H])=C(Cl)C([2H])=C3[2H])[2H]
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
>2 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
2934.99.9001
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
DMSO 10.0 26.68
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 374.81 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.
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. 1: Lee JY, Jang JS. The effect of PPIs Alone, PPIs plus cytoprotective agent, and H2RA plus cytoprotective agent on ulcer healing after endoscopic submucosal dissection: A prospective randomized controlled trial. Arab J Gastroenterol. 2021 Feb 4:S1687-1979(20)30115-5. doi: 10.1016/j.ajg.2020.09.007. Epub ahead of print. PMID: 33551349. 2: Tanigawa T, Watanabe T, Higashimori A, Shimada S, Kitamura H, Kuzumoto T, Nadatani Y, Otani K, Fukunaga S, Hosomi S, Tanaka F, Kamata N, Nagami Y, Taira K, Shiba M, Suda W, Hattori M, Fujiwara Y. Rebamipide ameliorates indomethacin- induced small intestinal damage and proton pump inhibitor-induced exacerbation of this damage by modulation of small intestinal microbiota. PLoS One. 2021 Jan 28;16(1):e0245995. doi: 10.1371/journal.pone.0245995. PMID: 33507971; PMCID: PMC7842908. 3: Okawa S, Sumimoto Y, Masuda K, Ogawara KI, Maruyama M, Higaki K. Improvement of lipid solubility and oral bioavailability of a poorly water- and poorly lipid-soluble drug, rebamipide, by utilizing its counter ion and SNEDDS preparation. Eur J Pharm Sci. 2021 Apr 1;159:105721. doi: 10.1016/j.ejps.2021.105721. Epub 2021 Jan 19. PMID: 33482317. 4: Shoji J, Inada N, Tomioka A, Yamagami S. Assessment of mucin-related gene alterations following treatment with rebamipide ophthalmic suspension in Sjögren's syndrome-associated dry eyes. PLoS One. 2020 Nov 24;15(11):e0242617. doi: 10.1371/journal.pone.0242617. PMID: 33232357; PMCID: PMC7685436. 5: Xu N, Zhang C, Jing L, Mou S, Cao X, Yu Z. Protective effect and mechanism of rebamipide on NSAIDs associated small bowel injury. Int Immunopharmacol. 2021 Jan;90:107136. doi: 10.1016/j.intimp.2020.107136. Epub 2020 Nov 18. PMID: 33218942. 6: Kulchavenya EV. [A new approach to understanding the pathogenesis and treatment of infectious and inflammatory diseases of the urogenital tract]. Urologiia. 2020 Nov;(5):99-105. Russian. PMID: 33185356. 7: Liu J, Xiong Z, Geng X, Cui M. Rebamipide with Proton Pump Inhibitors (PPIs) versus PPIs Alone for the Treatment of Endoscopic Submucosal Dissection-Induced Ulcers: A Meta-analysis. Biomed Res Int. 2020 Sep 28;2020:7196782. doi: 10.1155/2020/7196782. PMID: 33062694; PMCID: PMC7539128. 8: Sakane Y, Yamaguchi M, Shiraishi A. Corrigendum to "Retrospective Observational Study on Rebamipide Ophthalmic Suspension on Quality of Life of Dry Eye Disease Patients". J Ophthalmol. 2020 Sep 18;2020:8486704. doi: 10.1155/2020/8486704. Erratum for: J Ophthalmol. 2019 May 2;2019:8145731. PMID: 33014444; PMCID: PMC7519998. 9: Xu Y, Xiong L, Li Y, Jiang X, Xiong Z. Diagnostic methods and drug therapies in patients with ischemic colitis. Int J Colorectal Dis. 2021 Jan;36(1):47-56. doi: 10.1007/s00384-020-03739-z. Epub 2020 Sep 16. PMID: 32936393; PMCID: PMC7493065. 10: Abdel-Wahab BA, Ali FEM, Alkahtani SA, Alshabi AM, Mahnashi MH, Hassanein EHM. Hepatoprotective effect of rebamipide against methotrexate-induced hepatic intoxication: role of Nrf2/GSK-3β, NF-κβ-p65/JAK1/STAT3, and PUMA/Bax/Bcl-2 signaling pathways. Immunopharmacol Immunotoxicol. 2020 Oct;42(5):493-503. doi: 10.1080/08923973.2020.1811307. Epub 2020 Aug 29. PMID: 32865051. 11: Kim JW, Jeong Y, Park SJ, Jin H, Lee J, Ju JH, Ji GE, Park SH. Influence of proton pump inhibitor or rebamipide use on gut microbiota of rheumatoid arthritis patients. Rheumatology (Oxford). 2021 Feb 1;60(2):708-716. doi: 10.1093/rheumatology/keaa316. PMID: 32789440. 12: Otsuka Y, Utsunomiya Y, Umeda D, Yonemochi E, Kawano Y, Hanawa T. Effect of Polymers and Storage Relative Humidity on Amorphous Rebamipide and Its Solid Dispersion Transformation: Multiple Spectra Chemometrics of Powder X-Ray Diffraction and Near-Infrared Spectroscopy. Pharmaceuticals (Basel). 2020 Jul 10;13(7):147. doi: 10.3390/ph13070147. PMID: 32664249; PMCID: PMC7407760. 13: Van Ngo H, Park C, Tran TTD, Nguyen VH, Lee BJ. Mechanistic understanding of salt-induced drug encapsulation in nanosuspension via acid-base neutralization as a nanonization platform technology to enhance dissolution rate of pH- dependent poorly water-soluble drugs. Eur J Pharm Biopharm. 2020 Sep;154:8-17. doi: 10.1016/j.ejpb.2020.07.001. Epub 2020 Jul 4. PMID: 32634569. 14: Markovic M, Zur M, Dahan A, Cvijić S. Biopharmaceutical characterization of rebamipide: The role of mucus binding in regional-dependent intestinal permeability. Eur J Pharm Sci. 2020 Sep 1;152:105440. doi: 10.1016/j.ejps.2020.105440. Epub 2020 Jun 29. PMID: 32615260. 15: Zvyaglova MY, Knyazev OV, Parfenov AI. [Pharmacological and clinical feature of rebamipide: new therapeutic targets]. Ter Arkh. 2020 Apr 27;92(2):104-111. Russian. doi: 10.26442/00403660.2020.02.000569. PMID: 32598727. 16: Ivashkin VT, Trukhmanov AS, Gonik MI. [Rebamipide using in gastroesophageal reflux disease treatment]. Ter Arkh. 2020 May 19;92(4):98-104. Russian. doi: 10.26442/00403660.2020.04.000568. PMID: 32598706. 17: Elmansy RA, Seleem HS, Mahmoud AR, Hassanein EHM, Ali FEM. Rebamipide potentially mitigates methotrexate-induced nephrotoxicity via inhibition of oxidative stress and inflammation: A molecular and histochemical study. Anat Rec (Hoboken). 2021 Mar;304(3):647-661. doi: 10.1002/ar.24482. Epub 2020 Jul 17. PMID: 32589351. 18: Hou D, Yang M, Hu Z, Yang L. Effects of rebamipide for chronic atrophic gastritis: A protocol for systematic review and meta-analysis. Medicine (Baltimore). 2020 Jun 19;99(25):e20620. doi: 10.1097/MD.0000000000020620. PMID: 32569191; PMCID: PMC7310858. 19: Baek IH, Ha DK, Joo DS, Kim MJ. Interspecies differences on pharmacokinetics of rebamipide following oral administration to rats and dogs. Biopharm Drug Dispos. 2020 Jun;41(6):268-272. doi: 10.1002/bdd.2247. Epub 2020 Jul 15. PMID: 32557753. 20: Nagai N, Seiriki R, Deguchi S, Otake H, Hiramatsu N, Sasaki H, Yamamoto N. Hydrogel Formulations Incorporating Drug Nanocrystals Enhance the Therapeutic Effect of Rebamipide in a Hamster Model for Oral Mucositis. Pharmaceutics. 2020 Jun 9;12(6):532. doi: 10.3390/pharmaceutics12060532. PMID: 32527029; PMCID: PMC7356607.