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MedKoo Cat#: 461266 | Name: Revaprazan

Description:

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

Revaprazan is a novel acid pump antagonist (APA). It is a selective potassium-competitive acid blocker, to be specific, that reversibly inhibits gastric H(+)/K(+)-ATPase and shows effective acid suppression comparable to PPIs.

Chemical Structure

Revaprazan
Revaprazan
CAS#199463-33-7 (free base)

Theoretical Analysis

MedKoo Cat#: 461266

Name: Revaprazan

CAS#: 199463-33-7 (free base)

Chemical Formula: C22H23FN4

Exact Mass: 362.1907

Molecular Weight: 362.45

Elemental Analysis: C, 72.90; H, 6.40; F, 5.24; N, 15.46

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
178307-42-1 (HCl) 199463-33-7 (free base)
Synonym
Revaprazan; SB 641257; SB-641257; SB641257;
IUPAC/Chemical Name
N-(4-fluorophenyl)-4,5-dimethyl-6-(1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)pyrimidin-2-amine
InChi Key
LECZXZOBEZITCL-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H23FN4/c1-14-15(2)24-22(25-19-10-8-18(23)9-11-19)26-21(14)27-13-12-17-6-4-5-7-20(17)16(27)3/h4-11,16H,12-13H2,1-3H3,(H,24,25,26)
SMILES Code
CC1N(C2=C(C)C(C)=NC(NC3=CC=C(F)C=C3)=N2)CCC4=C1C=CC=C4
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 362.45 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
1: Kim JH, Kim EH, Ock C, Hong H, Kim YJ, Kwon KA, Park DK, Hahm KB. Mitigating endoplasmic reticulum stress with revaprazan ameliorates stress-related mucosal disease. J Gastroenterol Hepatol. 2012 Jan;27(1):120-9. doi: 10.1111/j.1440-1746.2011.06838.x. PubMed PMID: 21722181. 2: Jo Y, Park E, Ahn SB, Jo YK, Son B, Kim SH, Park YS, Kim HJ. A Proton Pump Inhibitor's Effect on Bone Metabolism Mediated by Osteoclast Action in Old Age: A Prospective Randomized Study. Gut Liver. 2015 Sep 23;9(5):607-14. doi: 10.5009/gnl14135. PubMed PMID: 25473078; PubMed Central PMCID: PMC4562777. 3: Choi HY, Noh YH, Jin SJ, Kim YH, Kim MJ, Sung H, Jang SB, Lee SJ, Bae KS, Lim HS. Bioavailability and tolerability of combination treatment with revaprazan 200 mg + itopride 150 mg: a randomized crossover study in healthy male Korean volunteers. Clin Ther. 2012 Sep;34(9):1999-2010. doi: 10.1016/j.clinthera.2012.07.004. Epub 2012 Aug 1. PubMed PMID: 22858177. 4: Jung JW, Kang HR, Kwon JW, Kim TE, Lee SH, Hong KS, Yu KS, Cho SH. The potential inhibitory effect of revaprazan, an acid pump antagonist, on anticoagulation with warfarin. Tohoku J Exp Med. 2011 Aug;224(4):293-300. PubMed PMID: 21799301. 5: Oak JH, Chung WC, Jung SH, Choi KH, Kim EJ, Kang BK, Kang BR, Kong SE, Paik CN, Lee KM. [Effect of acid pump antagonist (Revaprazan, Revanex(R)) on result of 13C urea breath test in patients with Helicobacter pylori associated peptic ulcer disease]. Korean J Gastroenterol. 2011 Jan;57(1):8-13. Korean. PubMed PMID: 21258195. 6: Lee JS, Cho JY, Song H, Kim EH, Hahm KB. Revaprazan, a novel acid pump antagonist, exerts anti-inflammatory action against Helicobacter pylori-induced COX-2 expression by inactivating Akt signaling. J Clin Biochem Nutr. 2012 Sep;51(2):77-83. doi: 10.3164/jcbn.11-94. Epub 2012 Jul 20. PubMed PMID: 22962522; PubMed Central PMCID: PMC3432830. 7: Park SY. [Effect of acid pump antagonist (Revaprazan, Revanex(R)) on the result of 13C urea breath test in the patients with Helicobacter pylori associated peptic ulcer disease]. Korean J Gastroenterol. 2011 Jan;57(1):1-2. Korean. PubMed PMID: 21258193. 8: Li W, Yang Y, Tian Y, Xu X, Chen Y, Mu L, Zhang Y, Fang L. Preparation and in vitro/in vivo evaluation of revaprazan hydrochloride nanosuspension. Int J Pharm. 2011 Apr 15;408(1-2):157-62. doi: 10.1016/j.ijpharm.2011.01.059. Epub 2011 Feb 2. PubMed PMID: 21295124. 9: Lim YJ, Phan TM, Dial EJ, Graham DY, Lichtenberger LM. In vitro and in vivo protection against indomethacin-induced small intestinal injury by proton pump inhibitors, acid pump antagonists, or indomethacin-phosphatidylcholine. Digestion. 2012;86(2):171-7. doi: 10.1159/000339882. Epub 2012 Aug 14. PubMed PMID: 22907267; PubMed Central PMCID: PMC3477857. 10: Ock CY, Lim YJ, Kim YJ, Chung JW, Kwon KA, Kim JH, Hahm KB. Acid pump antagonist-provoked HSP27 dephosphorylation and accentuation rescues stomach from indomethacin-induced damages. J Dig Dis. 2011 Apr;12(2):71-81. doi: 10.1111/j.1751-2980.2011.00482.x. PubMed PMID: 21401892. 11: Song W, Zhang X, Li S, Xu W. Design, synthesis, and preliminary activity evaluation of novel pyrimidine derivatives as acid pump antagonists. Chem Biol Drug Des. 2015 Mar;85(3):306-14. doi: 10.1111/cbdd.12390. Epub 2014 Sep 8. PubMed PMID: 24995399. 12: Kim HK, Park SH, Cheung DY, Cho YS, Kim JI, Kim SS, Chae HS, Kim JK, Chung IS. Clinical trial: inhibitory effect of revaprazan on gastric acid secretion in healthy male subjects. J Gastroenterol Hepatol. 2010 Oct;25(10):1618-25. doi: 10.1111/j.1440-1746.2010.06408.x. PubMed PMID: 20880169. 13: Kim YG, Jang BI, Kim TN. A matched case-control study of a novel Acid-pump antagonist and proton-pump inhibitor for the treatment of iatrogenic ulcers caused by endoscopic submucosal dissection. Gut Liver. 2010 Mar;4(1):25-30. doi: 10.5009/gnl.2010.4.1.25. Epub 2010 Mar 25. PubMed PMID: 20479909; PubMed Central PMCID: PMC2871596. 14: Inatomi N, Matsukawa J, Sakurai Y, Otake K. Potassium-competitive acid blockers: Advanced therapeutic option for acid-related diseases. Pharmacol Ther. 2016 Dec;168:12-22. doi: 10.1016/j.pharmthera.2016.08.001. Epub 2016 Aug 8. Review. PubMed PMID: 27514776. 15: Park JH, Lee DH, Kim JY, Park SY, Yoon H, Park YS, Kim N, Jeong SH, Kim JW, Lee SH, Hwang JH, Jung HC. Gastroesophageal reflux disease with laryngopharyngeal manifestation in Korea. Hepatogastroenterology. 2012 Nov-Dec;59(120):2527-9. doi: 10.5754/hge10294. PubMed PMID: 23178619. 16: Li W, Quan P, Zhang Y, Cheng J, Liu J, Cun D, Xiang R, Fang L. Influence of drug physicochemical properties on absorption of water insoluble drug nanosuspensions. Int J Pharm. 2014 Jan 2;460(1-2):13-23. doi: 10.1016/j.ijpharm.2013.10.038. Epub 2013 Oct 29. PubMed PMID: 24184036. 17: Yang ZC, Yu F, Wang YQ, Wei JF. Stereoselective Pharmacodynamics and Pharmacokinetics of Proton Pump Inhibitors. Curr Drug Metab. 2016 Mar 22. [Epub ahead of print] PubMed PMID: 27000074. 18: Park JH, Kim DS, Mustapha O, Yousaf AM, Kim JS, Kim DW, Yong CS, Youn YS, Oh KT, Lim SJ, Kim JO, Choi HG. Comparison of a revaprazan-loaded solid dispersion, solid SNEDDS and inclusion compound: Physicochemical characterisation and pharmacokinetics. Colloids Surf B Biointerfaces. 2018 Feb 1;162:420-426. doi: 10.1016/j.colsurfb.2017.12.017. Epub 2017 Dec 12. PubMed PMID: 29248606. 19: Mori H, Tonai-Kachi H, Ochi Y, Taniguchi Y, Ohshiro H, Takahashi N, Aihara T, Hirao A, Kato T, Sakakibara M, Kurebayashi Y. N-(2-hydroxyethyl)-N,2-dimethyl-8-{[(4R)-5-methyl-3,4-dihydro-2H-chromen-4-yl]ami no}imidazo[1,2-a]pyridine-6-carboxamide (PF-03716556), a novel, potent, and selective acid pump antagonist for the treatment of gastroesophageal reflux disease. J Pharmacol Exp Ther. 2009 Feb;328(2):671-9. doi: 10.1124/jpet.108.146415. Epub 2008 Nov 3. PubMed PMID: 18981288. 20: Han KS, Kim YG, Lee JW, Lee MG. Blood partition and protein binding of a new reversible proton pump inhibitor, YH1885. Biopharm Drug Dispos. 1998 Sep;19(6):413-5. PubMed PMID: 9737823.