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基本情報
- CAS
144675-97-8- 標準SMILES
NCCNc1ccc(NCCN)c2c1C(=O)c1ccncc1C2=O.O=C(O)/C=C/C(=O)O.O=C(O)/C=C/C(=O)O- 分子式
- C21H23N5O6
- 平均分子量
- 441.44 g/mol
名称と識別子
- 優先名称
- Pixantrone Dimaleate
- 現地名
- ピクサントロンマレイン酸塩
- 英語名
- Pixantrone Dimaleate
- 分子式
- C21H23N5O6
- 分子量
- 441.44
名称と別名
ピクサントロンマレイン酸塩Pixantrone maleateCS-1295Bbr 2778Dimalate saltBBR 2778 dimaleatePixatrone dimaleatePixantrone DimaleatePixantrone dimaleate (BBR-2778)Pixantrone dimaleate, 10 mM in DMSOPixantrone-dimaleate, BBR2778 dimaleate
データベース識別子
- CAS
144675-97-8- PubChem CID
- 6449873
- EC Number
- 680-661-5
物性
物理化学的性質
- 融点
- 192 ° · 192°
- 貯蔵温度
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- 溶解性
- 30 · DMSO:30.0(Max Conc. mg/mL);53.8(Max Conc. mM)H2O:5.0(Max Conc. mg/mL);9.0(Max Conc. mM)
- 外見
- A crystalline solid
- 色
- Blue to dark blue
- 水溶解度
- 2 O: · H2O: 2mg/mL, clear
- InChIKey
- GORZTPPEWDXGBU-BTJKTKAUSA-N
- SMILES
- C(/C(=O)O)=C/C(=O)O.N(C1=CC=C(NCCN)C2C(C3=CN=CC=C3C(=O)C1=2)=O)CCN
化学的性質
化学的特性Blue Solid
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
安全データ
- wgk
- WGK 3
- Hazard Classifications
- Muta. 2Repr. 2
- ストレージクラス
- 13 - Non Combustible Solids
化学と産業
応用分野
説明Pixantrone dimaleate was approved by European Medicine Agency (EMA) on May 10, 2012. It was developed and marketed as Pixuvri® by Cell Therapeutics in EU. (CTI Life Sciences).Pixantrone dimaleate is a DNA intercalating agent indicated as monotherapy for the treatment of adult patients with multiply relapsed or refractory aggressive Non-Hodgkin B-cell Lymphomas (NHL).Pixuvri® is available as lyophilised powder for infusion, containing 29 mg of free Pixantrone. The recommended dose is 50 mg/m2 of pixantrone on days 1, 8 and 15 of each 28-day cycle for up to 6 cycles.
天然物の起源Pixantrone dimaleate, also known as BBR 2778, was first synthesized by Professors Krapcho and Hacker at the University of Vermont. The University of Vermont and the Boehringer Mannheim Italia research center co-identified the in vitro tumor cell cytotoxicity.
使用Pixantrone is an antineoplastic drug belonging to group of antitumor antibiotics. Pixantrone is an anlogue of Mitoxantrone (M373425) and is just as potent in the treatment of multiple sclerosis with f ewer toxic effects on cardiac tissue. Studies suggest that Pixantrone significantly reduces amyloid beta (A beta(1-42)) neurotoxicity, a mechanism implicated in Alzheimer's disease.
調製方法
製造方法The manufacturing scale synthesis of pixantrone dimaleate relies on several process modifications from the original synthesis reported by Krapcho in 1994. This modified procedure has provided active pharmaceutical ingredient (API) in high purity (>99%) and is acceptable for use in pharmaceutical applications (Scheme 25). Beginning with pyridine 3,4-dicarboxylic acid (129), generation of the corresponding anhydride 130 proceeded in 76% yield upon treatment with refluxing Ac2O. Next, an AlCl3-promoted Friedel–Crafts reaction of 1,4-difluorobenzene (131) with 130 under reflux conditions provided a mixture of nicotinic acid isomers 132a/132b in 84% yield, which were carried directly to the next step. Cyclization with fuming H2SO4 yielded the desired difluorobenzo-isoquinoline-dione core 133, which was further functionalized with ethylenediamine (134) to provide the free base of pixantrone. Subjection of the pixantrone free base to aqueous acetic anhydride and maleic acid provided pixantrone dimaleate (XX) in 92% yield over 3 steps.Synthesis of pixantrone dimaleate
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