Vonoprazan Fumarate
[CAS# 1260141-27-2]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: Vonoprazan Fumarate
• Synonyms: TAK 438;5-(2-Fluorophenyl)-N-methyl-1-(3-pyridinylsulfonyl)-1H-pyrrole-3-methanamine 2-butenedioate
• Molecular Formula: C₁₇H₁₆FN₃O₂S^.C₄H₄O₄
• Molecular Weight: 461.46
• CAS Registry Number: 1260141-27-2
• EC Number: 863-483-4
• SMILES: CNCC1=CN(C(=C1)C2=CC=CC=C2F)S(=O)(=O)C3=CN=CC=C3.C(=C/C(=O)O)\C(=O)O

Properties

• Solubility: 15 mg/mL (DMSO)

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Hazard Statements: H302-H373
• Precautionary Statements: P260-P264-P270-P301+P317-P319-P330-P501

Discovory and Applicatios

Vonoprazan fumarate, a proton pump inhibitor (PPI), was discovered through rigorous pharmaceutical research aimed at developing more effective treatments for acid-related diseases, such as gastroesophageal reflux disease (GERD) and peptic ulcers. Traditional PPIs, while effective, often require acid activation for optimal efficacy, leading to delayed onset of action and potential treatment failures. Vonoprazan, however, boasts a novel mechanism of action by irreversibly binding to the proton pump enzyme, regardless of acid presence, resulting in rapid and sustained acid suppression. Discovered by Takeda Pharmaceutical Company, vonoprazan fumarate represented a breakthrough in acid suppression therapy and garnered significant attention for its clinical potential.

Vonoprazan is widely used in the management of GERD and peptic ulcers, providing rapid and sustained relief from symptoms such as heartburn, regurgitation, and epigastric pain.

Its rapid onset of action allows for quicker symptom relief compared to traditional PPIs, making it particularly beneficial for patients with severe or refractory symptoms.

Vonoprazan is increasingly utilized as part of triple or quadruple therapy regimens for Helicobacter pylori eradication. Its potent acid suppression enhances the effectiveness of antibiotics, leading to higher eradication rates and reducing the risk of treatment failure and antibiotic resistance.

Nonsteroidal anti-inflammatory drugs (NSAIDs) are known to cause gastric mucosal damage and ulcers. Vonoprazan has shown efficacy in preventing NSAID-induced gastric damage by suppressing acid secretion and maintaining gastric mucosal integrity.

Vonoprazan is also indicated for the management of Zollinger-Ellison syndrome, a rare condition characterized by excessive gastric acid secretion due to gastrin-secreting tumors (gastrinomas) in the pancreas or duodenum.

In critically ill patients or those undergoing anesthesia, vonoprazan may be used to prevent aspiration pneumonia by reducing gastric acid secretion and minimizing the risk of gastric contents refluxing into the lungs.

Vonoprazan can be prescribed for long-term maintenance therapy to prevent recurrence of acid-related diseases, such as GERD and peptic ulcers, in patients with a history of frequent symptomatic episodes or complications.