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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
Shandong Fuchuang Pharmaceutical Technology Co. , Ltd.
Tel
0531-88792816 18615587029
Email
fcpharm2006@126.com
Country
China
ProdList
126
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58
Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399 18927568969
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4428
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55
Jinan Baozhao Pharmaceutical Technology Co., Ltd.
Tel
0531-82371868 13210529039
Fax
0531-82371858
Email
baozhaopharm@163.com
Country
China
ProdList
141
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58
Shanghai Mixiu Chemical Co., Ltd.
Tel
18101936766
Fax
021-58583907
Email
eileen@shmychem.com
Country
China
ProdList
350
Advantage
55
Shandong Mingfeng Pharmaceutical and Technology Co. Ltd
Tel
-1345456643 15315114555
Fax
QQ:1345456643
Email
1345456643@qq.com
Country
China
ProdList
223
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58
Ningbo Zhenlei Chemical Co.,ltd.
Tel
0576-88808091 13958565781
Fax
+0576-88203603
Email
shuang.lin@zhenleichem.com
Country
China
ProdList
89
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58
Beijing Zhongshuo Pharmaceutical Technology Development Co., Ltd
Tel
010-53679529 13801208576
Fax
010-64215766
Email
sales.2@chinazhongshuo.com
Country
China
ProdList
99
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CHENGHUI PHARMACEUTICAL GROUP LTD
Tel
0531-58897070 15254140813
Fax
0531-58897046
Email
market@jnchsd.com
Country
China
ProdList
213
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
Advantage
55
ChemFuture PharmaTech (Jiangsu) Ltd
Tel
5108538618
Fax
86 510 85386988-8017
Email
suger.wang@chemfuture.com
Country
China
ProdList
832
Advantage
65
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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
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
Strong peptide cross-border e-commerce Co. LTD
Product
Vonoprazan fumarate 1260141-27-2
Price
US $20.00-15.00/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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