General
Preferred name
vonoprazan
Synonyms
TAK-438 ()
Vonoprazan fumarate ()
TAK 438 ()
Vonoprazan (fumarate) ()
Vonoprazan Fumarate (TAK-438) ()
Takecab ()
Vocinti ()
TAK-438 monofumarate ()
Vonoprazan monofumarate ()
TAK-438 (free base) ()
P&D ID
PD071923
CAS
1260141-27-2
881681-00-1
881681-01-2
Tags
available
drug
Approved by
PMDA
First approval
2014
2022
Drug indication
Gastroesophageal reflux disease
Helicobacter infection
Drug Status
approved
investigational
Max Phase
4.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCPRITION
a potassium-competitive proton pump blocker for the treatment of acid-related disorders
DESCRIPTION
Vonoprazan (TAK-438) is a first-in-class, potassium competitive acid blocker (P-CAB) class agent . It reduces gastric acid production via reversible inhibition of the gastric proton pump ATPase (a.k.a. gastric H+,K+-ATPase) . 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 . 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 .
(GtoPdb)
DESCRIPTION
Vonoprazan 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. It is used to treat acid-related diseases. It can be used for the treatment of gastroduodenal ulcer (including some drug-induced peptic ulcers) and reflux esophagitis, and can be combined with antibiotics for the eradication of Helicobacter pylori. It is a pyrrole derivative with a chemical structure that is completely different from the P-CABs developed to date in vitro. It inhibits basal gastric acid secretion in a dose-dependent manner, and the ID50 value is 1.26 mg/kg in vivo. It shows a potent and longer-lasting inhibitory effect on the histamine-stimulated gastric acid secretion in rats and dogs. It shows significant antisecretory activity through high accumulation and slow clearance from the gastric tissue. It is unaffected by the gastric secretory state. It was developed by Takeda and Otsuda together. It has been listed.
(BOC Sciences Bioactive Compounds)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Compound Sets
19
AdooQ Bioactive Compound Library
Axon Medchem Screening Library
BOC Sciences Bioactive Compounds
Cayman Chemical Bioactives
ChEMBL Approved Drugs
ChEMBL Drugs
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
Guide to Pharmacology
Other bioactive compounds
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
44
Molecular Weight
345.09
Hydrogen Bond Acceptors
5
Hydrogen Bond Donors
1
Rotatable Bonds
5
Ring Count
3
Aromatic Ring Count
3
cLogP
2.65
TPSA
63.99
Fraction CSP3
0.12
Chiral centers
0.0
Largest ring
6.0
QED
0.77
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Membrane Transporter/Ion Channel
Anti-infection
Target
H+/K+-ATPase
ATP4A
PCA blocker
Bacterial
Proton Pump
Potassium Channel
Indication
peptic ulcer disease (PUD)
MOA
potassium-competitive acid antagonist
Solubility
DMSO: ≥ 33 mg/mL
Source data
