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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
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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
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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..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
24200
Product name
Vonoprazan (fumarate)
Purity
≥98%
Packaging
500mg
Price
$43
Updated
2023/06/20
Cayman Chemical
Product number
24200
Product name
Vonoprazan (fumarate)
Purity
≥98%
Packaging
1g
Price
$76
Updated
2023/06/20
Cayman Chemical
Product number
24200
Product name
Vonoprazan (fumarate)
Purity
≥98%
Packaging
5g
Price
$293
Updated
2023/06/20
Cayman Chemical
Product number
24200
Product name
Vonoprazan (fumarate)
Purity
≥98%
Packaging
10g
Price
$417
Updated
2023/06/20
Usbiological
Product number
474195
Product name
TAK 438
Packaging
100mg
Price
$1168
Updated
2021/12/16
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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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Vonoprazan fumarate Suppliers

China 438 India 16 United Kingdom 2 United States 18 Global 474
AdooQ BioScience, LLC
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Accela ChemBio Inc.
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View Lastest Price from Vonoprazan fumarate manufacturers

Sinoway Industrial co., ltd.
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
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Vonoprazan Fumarate 1260141-27-2
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
99%min
Supply Ability
1000kg
Release date
2021-10-25
Strong peptide cross-border e-commerce Co. LTD
Product
Vonoprazan fumarate 1260141-27-2
Price
US $40.00-35.00/box
Min. Order
1box
Purity
99.9+
Supply Ability
2000box
Release date
2024-06-07

1260141-27-2, Vonoprazan fumarateRelated Search:

Fosaprepitant dimeglumine ETOFIBRATE Donepezil Hydrochloride Vonoprazan Vonoprazan FuMarate 5-(2-Fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde ALOGLIPTIN(ALOGLIPTINE, ALOGLIPTINA) AGOMELATINE Linagliptin Alogliptin benzoate Trelagliptin Trelagliptin succinate Teneligliptin Hydrobromide Esomeprazole R-(+)-Lansoprazole 2-PYRIMIDINAMINE, 4-(3,4-DIHYDRO-1-METHYL-2(1H)-ISOQUINOLINYL)-N-(4-FLUOROPHENYL)-5,6-DIMETHYL-, MONOHYDROCHLORIDE Pantoprazole Lansoprazole

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  • vonaprazan(TK-438)
  • 1-[5-(2-fluorophenyl)-1-pyridin-3-ylsulfonylpyrrol-3-yl]-N-methylmethanamine,(E)-4-oxopent-2-enoic acid
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  • 5-(2-Fluorophenyl)-N-methyl-1-(3-pyridinylsulfonyl)-1H-pyrrole-3-methanamine 2-butenedioate (Vonoprazan fumarate)
  • TAK-438,1260141-27-2 Fluorine Prazan
  • TAK-438 USP/EP/BP
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  • Vonoprazan Fumarate DISCONTINUED PLEASE SEE V767013
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  • C17H16FN3O2SC4H4O4
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