Vonoprazan fumarate
- Product Name
- 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
- Formula Weight
- 461.4634032
- MOL File
- 1260141-27-2.mol
Vonoprazan fumarate Property
- storage temp.
- Store at -20°C
- solubility
- insoluble in H2O; insoluble in EtOH; ≥18.9 mg/mL in DMSO
- form
- solid
- InChI
- InChI=1S/C17H16FN3O2S.C4H4O4/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;5-3(6)1-2-4(7)8/h2-9,11-12,19H,10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1+
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P312Call a POISON CENTER or doctor/physician if you feel unwell.
P321Specific treatment (see … on this label).
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
P403+P233Store in a well-ventilated place. Keep container tightly closed.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- 24200
- Product name
- Vonoprazan (fumarate)
- Purity
- ≥98%
- Packaging
- 500mg
- Price
- $43
- Updated
- 2023/06/20
- Product number
- 24200
- Product name
- Vonoprazan (fumarate)
- Purity
- ≥98%
- Packaging
- 1g
- Price
- $76
- Updated
- 2023/06/20
- Product number
- 24200
- Product name
- Vonoprazan (fumarate)
- Purity
- ≥98%
- Packaging
- 5g
- Price
- $293
- Updated
- 2023/06/20
- Product number
- 24200
- Product name
- Vonoprazan (fumarate)
- Purity
- ≥98%
- Packaging
- 10g
- Price
- $417
- Updated
- 2023/06/20
- Product number
- 474195
- Product name
- TAK 438
- Packaging
- 100mg
- Price
- $1168
- Updated
- 2021/12/16
Vonoprazan fumarate Chemical Properties,Usage,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
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View Lastest Price from Vonoprazan fumarate manufacturers
- Product
- TAK-438 1260141-27-2
- Price
- US $50.00-500.00/kg
- Min. Order
- 10kg
- Purity
- 0.99
- Supply Ability
- 20tans
- Release date
- 2023-10-30
- Product
- Vonoprazan Fumarate 1260141-27-2
- Price
- US $0.00/KG
- Min. Order
- 2KG
- Purity
- 99% min/GMP/PMDA/DMF
- Supply Ability
- 20tons
- Release date
- 2023-04-12
- Product
- Vonoprazan Fumarate (TAK-438) 1260141-27-2
- Price
- US $15.00/kg
- Min. Order
- 1kg
- Purity
- 99.912%
- Supply Ability
- 10ton
- Release date
- 2024-04-24