Vonoprazan fumarate

한글명:Vonoprazan fumarate

카스 번호1260141-27-2

상품명:Vonoprazan fumarate

CBNumberCB32628441

분자식C21H20FN3O6S

포뮬러 무게461.4634032

MOL 파일1260141-27-2.mol

화학적 성질

저장 조건	Store at -20°C
용해도	insoluble in H2O; insoluble in EtOH; ≥18.9 mg/mL in DMSO
물리적 상태	고체
물리적 상태	단단한 모양
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

그림문자(GHS)

그림문자(GHS)
신호 어

Warning
유해·위험 문구

H315：피부에 자극을 일으킴

H319：눈에 심한 자극을 일으킴

H335：호흡 자극성을 일으킬 수 있음
예방조치문구

P261：분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.

P264：취급 후에는 손을 철저히 씻으시오.

P264：취급 후에는 손을 철저히 씻으시오.

P271：옥외 또는 환기가 잘 되는 곳에서만 취급하시오.

P280：보호장갑/보호의/보안경/안면보호구를 착용하시오.

P302+P352：피부에 묻으면 다량의 물로 씻으시오.

P304+P340：흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.

P305+P351+P338：눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.

P312：불편함을 느끼면 의료기관(의사)의 진찰을 받으시오.

P321：(…) 처치를 하시오.

P332+P313：피부 자극이 생기면 의학적인 조치· 조언을 구하시오.

P337+P313：눈에 대한 자극이 지속되면 의학적인 조치· 조언를 구하시오.

P403+P233：용기는 환기가 잘 되는 곳에 단단히 밀폐하여 저장하시오.

P405：밀봉하여 저장하시오.

P501：...에 내용물 / 용기를 폐기 하시오.

Vonoprazan fumarate 화학적 특성, 용도, 생산

개요
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.
용도
Vonoprazan Fumarate is a novel potassium-?competitive acid blocker for the treatment of acid-?related diseases.
주요 응용
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.

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