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
- MDL Number:
- MFCD18633280
- MOL File:
- 1260141-27-2.mol
| storage temp. | Store at -20°C |
|---|---|
| solubility | insoluble in H2O; insoluble in EtOH; ≥18.9 mg/mL in DMSO |
| form | solid |
| InChIKey | ROGSHYHKHPCCJW-WLHGVMLRSA-N |
| SMILES | N1(S(C2=CC=CN=C2)(=O)=O)C(C2=CC=CC=C2F)=CC(CNC)=C1.C(O)(=O)/C=C/C(O)=O |
| FDA UNII | 4QW3X4AMLB |
| NCI Drug Dictionary | vonoprazan fumarate |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
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|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
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Vonoprazan fumarate price More Price(17)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Cayman Chemical | 24200 | Vonoprazan (fumarate) ≥98% | 1260141-27-2 | 500mg | $43 | 2023-06-20 | Buy |
| Cayman Chemical | 24200 | Vonoprazan (fumarate) ≥98% | 1260141-27-2 | 1g | $76 | 2023-06-20 | Buy |
| Cayman Chemical | 24200 | Vonoprazan (fumarate) ≥98% | 1260141-27-2 | 5g | $293 | 2023-06-20 | Buy |
| Cayman Chemical | 24200 | Vonoprazan (fumarate) ≥98% | 1260141-27-2 | 10g | $417 | 2023-06-20 | Buy |
| Usbiological | 474195 | TAK 438 | 1260141-27-2 | 100mg | $1168 | 2021-12-16 | Buy |
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.
Description
Vonoprazan is a selective, reversible, and potassium-competitive proton pump inhibitor that inhibits gastric H+/K+ ATPase (IC50 = 17 nM) but does not inhibit porcine Na+/K+ ATPase activity when used at a concentration of 10 μM. It maintains its inhibitory effect in both weakly acidic (pH 6.5) and neutral (pH 7.5) conditions with IC50 values of 19 and 28 nM, respectively. In vivo, vonoprazan (1, 2, and 4 mg/kg) inhibits histamine-stimulated acid secretion in a dose-dependent manner in rats, with complete inhibition when administered at a dose of 4 mg/kg. It also inhibits acid secretion for more than 48 hours in dogs when administered at doses ranging from 0.1 to 1 mg/kg.
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.
target
H,K-ATPase
References
[1]. yasunobu hori, jun matsukawa, toshiyuki takeuchi, et al. a study comparing the antisecretory effect of tak-438, a novel potassium-competitive acid blocker, with lansoprazole in animals. journal of pharmacology and experimental therapeutics, 2011, 337:797-804.
[2]. jun matsukawa, yasunobu hori, haruyuki nishida, et al. a comparative study on the modes of action of tak-438, a novel potassium-competitive acid blocker, and lansoprazole in primary cultured rabbit gastric glands. biochemical pharmacology, 2011, 81:1145-1151.
Vonoprazan fumarate Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Beijing Mesochem Technology Co.,Ltd | +8613651027935 | rachel@mesochem.com | China | 191 | 58 |
| TAIZHOU YUXIN BIOTECHNOLOGY CO,.LTD | +86-576-88902229;+86-0576-88902229 +8613968687450 | yuxin@yuxchem.com | China | 122 | 58 |
| Hangzhou ICH Biofarm Co., Ltd | +undefined8613073685410 | sales@ichemie.com | China | 985 | 58 |
| Hebei Mojin Biotechnology Co., Ltd | +8613288715578 | sales@hbmojin.com | China | 12453 | 58 |
| XI'AN TIANGUANGYUAN BIOTECH CO., LTD. | +86-029-86333380 18829239519 | sales06@tgybio.com | China | 962 | 58 |
| Changzhou Rokechem Technology Co., Ltd. | 18758118018 | sales001@rokechem.com | China | 255 | 58 |
| Firsky International Trade (Wuhan) Co., Ltd | +8615387054039 | admin@firsky-cn.com | China | 436 | 58 |
| shandong perfect biotechnology co.ltd | +86-53169958659; +8618596095638 | sales@sdperfect.com | China | 294 | 58 |
| Henan Tengmao Chemical Technology Co. LTD | +8615238638457 | salesvip2@hntmhg.com | China | 415 | 58 |
| Zibo Hangyu Biotechnology Development Co., Ltd | +86-0533-2185556 +8617865335152 | Mandy@hangyubiotech.com | China | 11013 | 58 |
View Lastest Price from Vonoprazan fumarate manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
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2024-04-10 | Vonoprazan Fumarate
1260141-27-2
|
US $0.00 / KG | 2KG | 99% min/GMP/PMDA/DMF | 20tons | Sinoway Industrial co., ltd. | |
 |
2024-03-12 | Vonoprazan Fumarate
1260141-27-2
|
US $0.00 / g | 1g | 98% HPLC | 1kg | shandong perfect biotechnology co.ltd | |
 |
2024-03-03 | Vonoprazan fumarate
1260141-27-2
|
US $110.00-90.00 / kilogram | 1kilogram | 99% | 10 tons/per week | Henan Tengmao Chemical Technology Co. LTD |
-
- Vonoprazan Fumarate
1260141-27-2
- US $0.00 / KG
- 99% min/GMP/PMDA/DMF
- Sinoway Industrial co., ltd.
-
- Vonoprazan Fumarate
1260141-27-2
- US $0.00 / g
- 98% HPLC
- shandong perfect biotechnology co.ltd
-
- Vonoprazan fumarate
1260141-27-2
- US $110.00-90.00 / kilogram
- 99%
- Henan Tengmao Chemical Technology Co. LTD