vonoprazan   Click here for help

GtoPdb Ligand ID: 11549

Synonyms: compound 13e [PMID: 22512618] | TAK-438 | TAK438 | Takecab® | TAKECAB® | Vocinti® | Voquezna®
Approved drug PDB Ligand
vonoprazan is an approved drug (Japan (2014), FDA (2022))
Compound class: Synthetic organic
Comment: Vonoprazan (TAK-438) is a first-in-class, potassium competitive acid blocker (P-CAB) class agent [4,7]. It reduces gastric acid production via reversible inhibition of the gastric proton pump ATPase (a.k.a. gastric H+,K+-ATPase) [1-2,7]. The compound appears to dock within the luminal vestibule of the proton pump's alpha subunit (ATP4A) and prevents K+ access to the ion binding domain, with a Ki of 3 nM for the wild type H+,K+-ATPase [7]. Vonoprazan has a faster onset of action than widely used proton pump inhibitors (PPI), doesn't require acid-mediated activation and provides long-lasting inhibition (due to its slow dissociation rate) of the gastric H+,K+-ATPase [5-6].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 72.37
Molecular weight 345.09
XLogP 2.5
No. Lipinski's rules broken 0
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Canonical SMILES CNCc1cc(n(c1)S(=O)(=O)c1cccnc1)c1ccccc1F
Isomeric SMILES CNCc1cc(n(c1)S(=O)(=O)c1cccnc1)c1ccccc1F
InChI InChI=1S/C17H16FN3O2S/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/h2-9,11-12,19H,10H2,1H3
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
ATP4A Pig Inhibitor Inhibition 7.7 pIC50 - 2
pIC50 7.7 (IC50 1.9x10-8 M) [2]
Description: Inhibition of H+/K+-ATPase activity in a gastric mucosal membrane microsomal fraction from pig stomach.
Ligand mentioned in the following text fields