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| Cas No.: | 881681-00-1 |
| Chemical Name: | Vonoprazan free base |
| Synonyms: | Vonoprazan;TAK-438 free base;TAK-438;TAK438 free base;TAK-438 (free base);1R5L3J156G;1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonyl-pyrrol-3-yl]-~{N}-methyl-methanamine;1-(5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl)-N-methylmethanamine;Vonoprazan [INN];1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1h-pyrrol-3-yl]-n-methylmethanamine;BCP13240;1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonylpyrrol-3-yl]- |
| SMILES: | CNCC1C=C(C2=C(F)C=CC=C2)N(C=1)S(=O)(=O)C3C=NC=CC=3 |
| Formula: | C17H16FN3O2S |
| M.Wt: | 345.39 |
| Purity: | >98% |
| Sotrage: | 2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO |
| Description: | TAK-438 (free base) is a novel P-CAB (potassium-competitive acid blocker) that reversibly inhibits H+/K+ ATPase with IC50 of 19 nM (pH 6.5), controls gastric acid secretion. |
| Target: | H+/K+ ATPase IC50 value: 19 nM [1] |
| In Vivo: | TAK-438 inhibits basal gastric acid secretion in a dose-dependent manner, and the ID50 value is 1.26 mg/kg. Intravenous administration of TAK-438 dose-dependently increases the pH of the gastric perfusate, and the increase in pH is sustained for 5 h after administration. At the 1 mg/kg dose, the pH plateaues 90 min after administration, and the highest pH value reached is 5.9 [2]. In addition, TAK-438 shows a potent and longer-lasting inhibitory effect on the histamine-stimulated gastric acid secretion in rats and dogs. TAK-438 shows significant antisecretory activity through high accumulation and slow clearance from the gastric tissue. TAK-438 is unaffected by the gastric secretory state, unlike PPIs [3]. |
| In Vitro: | TAK-438 is a pyrrole derivative with a chemical structure that is completely different from the P-CABs developed to date. TAK-438 inhibits gastric H+/K+ ATPase activity in a concentration-dependent manner. Under neutral conditions (pH 7.5), the inhibitory activity of TAK-438 is almost the same as that under weakly acidic conditions (pH 6.5). TAK-438 does not inhibit Na+/K+ ATPase activity even at concentration 500 times higher than their IC50 values against gastric H+/K+ ATPase activity. TAK-438 inhibits gastric H+/K+ ATPase in a K+ competitive manner with Ki of 3 nM [2]. |
| References: | [1]. Arikawa Y, et al. Discovery of a novel pyrrole derivative 1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine fumarate (TAK-438) as a potassium-competitive acid blocker (P-CAB). J Med Chem, 2012, 55(9), 4446-4456. [2]. Hori Y, et al. 1-[5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine monofumarate (TAK-438), a novel and potent potassium-competitive acid blocker for the treatment of acid-related diseases. J Pharmacol Exp Ther, 2010, 335(1), 231-238. [3]. Hori Y, et al. A study comparing the antisecretory effect of TAK-438, a novel potassium-competitive acid blocker, with lansoprazole in animals. J Pharmacol Exp Ther, 2011, 337(3), 797-804. |