Vonoprazan Fumurate

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

MedKoo CAT#: 565584

CAS#: 881681-01-2

Description: Vonoprazan Fumurate is a novel potassium-competitive acid blocker


Price and Availability

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Vonoprazan Fumurate is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 565584
Name: Vonoprazan Fumurate
CAS#: 881681-01-2
Chemical Formula: C21H20FN3O6S
Exact Mass: 461.1057
Molecular Weight: 461.4644
Elemental Analysis: C, 54.66; H, 4.37; F, 4.12; N, 9.11; O, 20.80; S, 6.95


Synonym: TAK-438; TAK 438; TAK438

IUPAC/Chemical Name: 1-(5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl)-N-methylmethanamine fumarate

InChi Key: ROGSHYHKHPCCJW-WLHGVMLRSA-N

InChi Code: InChI=1S/C17H16FN3O2S.C4H4O4/c1-19-10-13-9-17(15-6-2-3-7-16(15)18)21(12-13)24(22,23)14-5-4-8-20-11-14;5-3(6)1-2-4(7)8/h2-9,11-12,19H,10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

SMILES Code: CNCC1=CN(S(=O)(C2=CC=CN=C2)=O)C(C3=CC=CC=C3F)=C1.O=C(O)/C=C/C(O)=O


Technical Data

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).

Harmonized System Code:
2934.99.90.01


References

1: Masaoka T, Kameyama H, Yamane T, Yamamoto Y, Takeuchi H, Suzuki H, Kitagawa Y, Kanai T. Pathophysiology of Potassium-competitive Acid Blocker-refractory Gastroesophageal Reflux and the Potential of Potassium-competitive Acid Blocker Test. J Neurogastroenterol Motil. 2018 Oct 1;24(4):577-583. doi: 10.5056/jnm18036. PubMed PMID: 30347936; PubMed Central PMCID: PMC6175552.

2: Matsukawa J, Inatomi N, Nishida H, Tsukimi Y. [Pharmacological characteristics and clinical efficacies of a novel potassium-competitive acid blocker, vonoprazan fumarate]. Nihon Yakurigaku Zasshi. 2018;152(3):104-110. doi: 10.1254/fpj.152.104. Japanese. PubMed PMID: 30185727.

3: Sugano K. Vonoprazan fumarate, a novel potassium-competitive acid blocker, in the management of gastroesophageal reflux disease: safety and clinical evidence to date. Therap Adv Gastroenterol. 2018 Jan 9;11:1756283X17745776. doi: 10.1177/1756283X17745776. eCollection 2018. Review. PubMed PMID: 29383028; PubMed Central PMCID: PMC5784563.

4: Suzuki N, Hiraga J, Takagi Y, Tsuzuki T, Uematsu N, Kagami Y. Immune thrombocytopenia induced by vonoprazan fumarate: a single center retrospective study. Ann Hematol. 2018 Apr;97(4):741-742. doi: 10.1007/s00277-017-3206-4. Epub 2017 Dec 16. PubMed PMID: 29247400.

5: Luo Z, Liu A, Liu Y, Wang G, Chen X, Wang H, Li M, Zhang H, Qiu Y, Zhai H. Development of a stability- indicating HPLC method for simultaneous determination of ten related substances in vonoprazan fumarate drug substance. J Pharm Biomed Anal. 2018 Feb 5;149:133-142. doi: 10.1016/j.jpba.2017.11.011. Epub 2017 Nov 4. PubMed PMID: 29112902.

6: Martinucci I, Blandizzi C, Bodini G, Marabotto E, Savarino V, Marchi S, de Bortoli N, Savarino E. Vonoprazan fumarate for the management of acid-related diseases. Expert Opin Pharmacother. 2017 Aug;18(11):1145-1152. doi: 10.1080/14656566.2017.1346087. Epub 2017 Jul 6. Review. PubMed PMID: 28657473.

7: Qiao Y, Zhao J, Yue X, Zhang Y, Zhang R, Xu Y, Tang X, Liu X, Wang Q. Study on pharmacokinetics and bioequivalence of Vonoprazan pyroglutamate in rats by liquid chromatography with tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Aug 1;1059:56-65. doi: 10.1016/j.jchromb.2017.05.013. Epub 2017 May 22. PubMed PMID: 28578848.

8: Yamasaki H, Kawaguchi N, Nonaka M, Takahashi J, Morohashi A, Hirabayashi H, Moriwaki T, Asahi S. In vitro metabolism of TAK-438, vonoprazan fumarate, a novel potassium-competitive acid blocker. Xenobiotica. 2017 Dec;47(12):1027-1034. doi: 10.1080/00498254.2016.1203505. Epub 2016 Jul 14. PubMed PMID: 27414183.

9: Otake K, Sakurai Y, Nishida H, Fukui H, Tagawa Y, Yamasaki H, Karashima M, Otsuka K, Inatomi N. Characteristics of the Novel Potassium-Competitive Acid Blocker Vonoprazan Fumarate (TAK-438). Adv Ther. 2016 Jul;33(7):1140-57. doi: 10.1007/s12325-016-0345-2. Epub 2016 Jun 10. Review. PubMed PMID: 27287852.

10: Kogame A, Takeuchi T, Nonaka M, Yamasaki H, Kawaguchi N, Bernards A, Tagawa Y, Morohashi A, Kondo T, Moriwaki T, Asahi S. Disposition and metabolism of TAK-438 (vonoprazan fumarate), a novel potassium-competitive acid blocker, in rats and dogs. Xenobiotica. 2017 Mar;47(3):255-266. doi: 10.1080/00498254.2016.1182667. Epub 2016 May 26. PubMed PMID: 27225050.

11: Matsukawa J, Kogame A, Tagawa Y, Inatomi N. Radiographic Localization Study of a Novel Potassium-Competitive Acid Blocker, Vonoprazan, in the Rat Gastric Mucosa. Dig Dis Sci. 2016 Jul;61(7):1888-94. doi: 10.1007/s10620-016-4100-y. Epub 2016 Mar 9. PubMed PMID: 26961787.

12: Yoneyama T, Teshima K, Jinno F, Kondo T, Asahi S. A validated simultaneous quantification method for vonoprazan (TAK-438F) and its 4 metabolites in human plasma by the liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Mar 15;1015-1016:42-49. doi: 10.1016/j.jchromb.2016.01.051. Epub 2016 Feb 3. PubMed PMID: 26896571.

13: Liu L, Cao N, Ma X, Xiong K, Sun L, Zou Q. Identification, characterization, and high-performance liquid chromatography quantification of process-related impurities in vonoprazan fumarate. J Sep Sci. 2016 Apr;39(7):1232-41. doi: 10.1002/jssc.201501154. Epub 2016 Mar 10. PubMed PMID: 26843471.

14: Matsukawa J, Inatomi N, Otake K. [Pharmacological and clinical profiles of a novel potassium-competitive acid blocker, vonoprazan fumarate (Takecab(®) 10 mg and 20 mg)]. Nihon Yakurigaku Zasshi. 2015 Nov;146(5):275-82. doi: 10.1254/fpj.146.275. Review. Japanese. PubMed PMID: 26558313.

15: Echizen H. The First-in-Class Potassium-Competitive Acid Blocker, Vonoprazan Fumarate: Pharmacokinetic and Pharmacodynamic Considerations. Clin Pharmacokinet. 2016 Apr;55(4):409-18. doi: 10.1007/s40262-015-0326-7. Review. PubMed PMID: 26369775.

16: Arikawa Y, Nishida H, Kurasawa O, Hasuoka A, Hirase K, Inatomi N, Hori Y, Matsukawa J, Imanishi A, Kondo M, Tarui N, Hamada T, Takagi T, Takeuchi T, Kajino M. Discovery of a novel pyrrole derivative 1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamin e fumarate (TAK-438) as a potassium-competitive acid blocker (P-CAB). J Med Chem. 2012 May 10;55(9):4446-56. doi: 10.1021/jm300318t. Epub 2012 Apr 30. PubMed PMID: 22512618.