Vonoprazan fumarate
- CAS No.
- 1260141-27-2
- Chemical Name:
- Vonoprazan fumarate
- Synonyms
- Vonoprazan FuMarate;Vonaprazan;5-(2-Fluorophenyl)-N-methyl-1-(3-pyridinylsulfonyl)-1H-pyrrole-3-methanamine 2-butenedioate (Vonoprazan);Vonaprazan(TAK-438);Vonoprazon Fumarate;Vonoprazan fumarate(TAK-438);vonoprazan(tak-438)1260141-27-2;5-(2-Fluorophenyl)-N-methyl-1-(3-pyridinylsulfonyl)-1H-pyrrole-3-methanamine 2-butenedioate;1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonylpyrrol-3-yl]-N-methylmethanamine,(E)-4-oxopent-2-enoic acid;AK-438
- CBNumber:
- CB32628441
- Molecular Formula:
- C21H20FN3O6S
- Molecular Weight:
- 461.4634032
- MOL File:
- 1260141-27-2.mol
- Modify Date:
- 2024/6/7 16:47:56
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P362+P364-P332+P313-P337+P313-P403+P233-P405-P501 | |||||||||
| NFPA 704 |
|
Vonoprazan fumarate Chemical Properties,Uses,Production
Description
Vonoprazan fumarate (Takecab®), discovered and developed by Takeda and Otsuka, was approved by the PMDA of Japan in December 2014, and is indicated for the treatment of gastric ulcer, duodenal ulcer and reflux esophagitis. Vonoprazan fumarate has a novel mechanism of action called potassium-competitive acid blockers, which competitively inhibit the binding of potassium ions to H+, K+-ATPase (also known as the proton pump) in the final step of gastric acid secretion in gastric parietal cells. Vonoprazan does not inhibit Na+, K+-ATPase activity even at concentrations 500 times higher than that of their IC50 values against gastric H+, K+-ATPase activity. Furthermore, the drug is unaffected by the gastric secretory state, unlike PPIs.
Uses
Vonoprazan Fumarate is a novel potassium-?competitive acid blocker for the treatment of acid-?related diseases.
Application
Vonoprazan fumarate is an oral, newly synthesised potassium-competitive acid blocker (P-CAB) with antisecretory activity. It is also a proton pump inhibitor (PPI) reversibly inhibiting H+/K+, ATPase. It is mainly used in the treatment of acid-related diseases such as GERD and peptic ulcer disease.
Synthesis
Commercially available 2-fluoroacetophenone (283) was brominated to yield a-bromo-acetophenone derivative 284. This compound was treated with ethyl 2-cyanoacetate (285) under basic conditions to provide ketoester 286 in essentially quantitative yield. Next, intramolecular condensation of 286 upon treatment of 4 M HCl furnished the tri-substituted pyrrole 287 in 53% yield. Reduction of the chloride under hydrogenolytic conditions facilitated arrival at pyrrole 288, albeit in just 18% yield. Subsequent diisobutylaluminium hydride (DIBAL) reduction, followed by the oxidation with tetrapropylammonium perruthenate (TPAP) and 4-methylmorpholine N-oxide (NMMO) afforded the corresponding aldehyde 290 in 60% yield across the 2 steps. Next, N-pyrrole substitution with pyridine- 3-sulfonyl chloride 291 gave rise to N-sulfonylpyrrole 292 in 82% yield. Reductive amination of 292 afforded amine 293, which was treated with fumaric acid (294) via co-crystallization to provide vonoprazan fumarate (XXXVI) in 74% for the two steps.
Vonoprazan fumarate Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Dr. Reddy's Laboratories Ltd | +91-4049002900 +91-4049002900 | Hyderabad, India | 165 | 58 | Inquiry |
| SHOBHA LIFE SCIENCES PRIVATE LIMITED | +919121212469 | Hyderabad, India | 31 | 58 | Inquiry |
| Veer Pharmachem | +91-02645661117 +91-9879471589 | Gujarat, India | 39 | 58 | Inquiry |
| Metrochem API Private Limited | +91-4069069999 +91-4069069999 | Telangana, India | 78 | 58 | Inquiry |
| Centaur Pharmaceuticals Pvt Ltd | +912266499100 | Mumbai, India | 33 | 58 | Inquiry |
| Anlon Healthcare Pvt Ltd | +91-2812562538 +91-7069690081 | Gujarat, India | 54 | 58 | Inquiry |
| Mehta API Pvt. Ltd. | +91-9920552082 +91-9920552082 | Maharashtra, India | 33 | 58 | Inquiry |
| Morepen Laboratories Ltd | +91-7017029282 +91-9818305894 | Haryana, India | 34 | 58 | Inquiry |
| Ami Lifesciences Pvt Ltd | +91-9426998100 +91-9426998100 | Gujarat, India | 62 | 58 | Inquiry |
| Maithri Drugs Pvt Ltd | +91-9059204566 +91-9848881740 | Telangana, India | 64 | 58 | Inquiry |