ダパグリフロジンプロピレングリコール水和物

危険有害性情報のコード(GHS)

• 絵表示(GHS)

  

• 注意喚起語

  Warning

• 危険有害性情報

  H302：飲み込むと有害

  H315：皮膚刺激

  H319：強い眼刺激

  H335：呼吸器への刺激のおそれ

• 注意書き

  P261：粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。

  P280：保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。

  P301+P312：飲み込んだ場合：気分が悪い時は医師に連絡する こと。

  P302+P352：皮膚に付着した場合：多量の水と石鹸で洗うこと。

  P305+P351+P338：眼に入った場合：水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。

ダパグリフロジンプロピレングリコール水和物 化学特性,用途語,生産方法

• 効能

  糖尿病治療薬, SGLT-2阻害薬

• 商品名

  フォシーガ (アストラゼネカ)

• 説明

  Dapagliflozin propanediol monohydrate is the first approved sodium-glucose cotransporter protein 2 (SGLT2) inhibitor. It is indicated for the treatment of type 2 diabetes. When combined with diet and exercise in adults, dagliflozin helps improve glycaemic control by inhibiting glucose reabsorption in the proximal tubules of renal units and causing glycosuria. Dagliflozin can be given alone or in combination with insulin or other oral hypoglycaemic agents as adjunctive therapy.
  Dagliflozin was originally approved by the FDA on 8 January 2014 for use in combination with diet and exercise to improve glycemic control in adults with type 2 diabetes. It was later approved in April 2021 to reduce the risk of declining kidney function, kidney failure, cardiovascular death and hospitalisation for heart failure in adults with chronic kidney disease.

• 使用

  Dapagliflozin Propanediol Hydrate is an SGLT2 inhibitor, which can be used for the treatment of diabetes.

• 定義

  ChEBI: A hydrate that consists of dapagliflozin compounded with (S)-propylene glycol and hydrate in a (1:1:1) ratio. Used to improve glycemic control, along with diet and exercise, in adults with type 2 diabetes.

• 臨床応用

  The most likely process-scale synthesis has been described in a literature publication and patent, and this is summarized in the scheme below. The synthesis began with global silylation glucolactone 63 to form tetrasiloxide 64. In parallel, commercial 5-bromo-2-chlorobenzoyl acid (65) was converted to the corresponding acid chloride with oxalyl chloride. Subsequently, this acid chloride was subjected to Friedel-Crafts acylation with ethyl phenyl ether (“phenetole”) in the presence of aluminum trichloride at low temperature to give benzophenone 66 in 91% yield. Next, the carbonyl functionality within 66 was removed upon treatment with triethylsilane and boron trifluoride-etherate, producing 5-bromo-2-chloro- 4'-ethoxydiphenylmethane 67 in 75% yield as the aglycon partner. Aryl bromide 67 was subjected to lithium halogen exchange conditions and subsequent exposure to lactone 64, which gave a mixture of lactols which were then immediately subjected to methanesulfonic acid to provide glucol 68 in 85% yield. The anomeric methoxy group of 68 was reduced with triethylsilane and boron trifluoride-etherate followed by peracetylation to deliver α-C-glycoside tetra-acetate 69 in 55% (two steps) after recrystalliaztion in ethanol. Hydrolysis of polyacetate 69 with lithium hydroxide gave dapagliflozin in quantitative yield, and upon treatment with propanediol in water, dapagliflozin propanediol hydrate (X) was produced.

ダパグリフロジンプロピレングリコール水和物 生産企業

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ダパグリフロジンプロピレングリコール水和物 スペクトルデータ(¹HNMR)