Idarubicinol | 86189-66-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 蒽环类药物
• 英文名称: Idarubicinol
• 英文别名: (7S,9S)-7-<(3'-amino-2',3',6'-trideoxy-α-L-lyxohexapyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-<1-(S)-hydroxyethyl>-5,12-naphthacenedione；13(S)-dihydro-4-demethoxydaunorubicin；4-demethoxy-13-dihydrodaunorubicin；(7S,9S)-7-[(3'-amino-2',3',6'-trideoxy-α-L-lyxohexapyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-(1-(S)-hydroxyethyl)-5,12-naphthacenedione；(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-[(1S)-1-hydroxyethyl]-8,10-dihydro-7H-tetracene-5,12-dione
• CAS: 86189-66-4
• 化学式: C₂₆H₂₉NO₉
• 分子量: 499.518
• InChiKey: KMIBSUUWQWSRQV-BAYOIBAISA-N

物化性质

• 溶解度：
  可溶于氯仿、DMSO、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  180
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Idarubicinol 生成
  参考文献：
  名称：

  13（R）-和13（S）-二氢-4-脱甲氧基-柔红霉素的全合成。修订4-去甲氧基柔红霉素的微生物和哺乳动物还原产物的立体化学

  摘要：

  13（S）-二氢-4-脱甲氧基柔红霉素而不是13（R）-异构体的性质对应于4-脱甲氧基金红霉素-红霉素的微生物和哺乳动物还原产物的性质。

  DOI：

  10.1016/s0040-4039(01)81761-5
• 作为产物：
  描述：

  1-chloro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxohexopyranose 在 silver trifluoromethanesulfonate 作用下， 生成 Idarubicinol
  参考文献：
  名称：

  13（R）-和13（S）-二氢-4-脱甲氧基-柔红霉素的全合成。修订4-去甲氧基柔红霉素的微生物和哺乳动物还原产物的立体化学

  摘要：

  13（S）-二氢-4-脱甲氧基柔红霉素而不是13（R）-异构体的性质对应于4-脱甲氧基金红霉素-红霉素的微生物和哺乳动物还原产物的性质。

  DOI：

  10.1016/s0040-4039(01)81761-5

文献信息

• Anthracyclines and their metabolism in human liver microsomes and the participation of the new microsomal carbonyl reductase
  作者：Adam Skarka、Lucie Škarydová、Hana Štambergová、Vladimír Wsól

  DOI：10.1016/j.cbi.2010.12.016

  日期：2011.5

  kinetic values of direct reduction and the reduction of aglycone were calculated. These results were compared to previously published data for human liver cytosol. In addition, the participation of the newly determined human liver microsomal carbonyl reductase was studied. No reduction of DOX into DOXOL was detected. Nevertheless, the involvement in reduction of DAUN into DAUNOL as well as IDA into IDAOL

  蒽环类药物（ANT）被广泛用于治疗各种形式的癌症。尽管使用它们有助于改善预期寿命，但受到严重不利影响（急性和慢性心脏毒性）的限制。据报道，AKR和SDR超家族的几种酶都参与了ANTs的减少。然而，所有这些都位于胞质区室中。已发现一种微粒体还原酶与异源生物的代谢有关，即11beta-HSD1，但尚未报道有关其在ANTs代谢中的作用的进一步信息。这项研究的目的是带来有关阿霉素，柔红霉素（DAUN）和伊达比星（IDA）的生物转化的新信息，不仅涉及人肝微粒体部分，还可以通过我们小组提纯的新型人类肝脏微粒体羰基还原酶进行纯化。ANTs在C-13位置的还原被认为是ANTs生物转化的主要途径。但是，我们用人肝微粒体级分进行的实验显示出不同的行为，特别是当孵育混合物中ANTs的浓度增加时。将微粒体级分与阿霉素，柔红霉素和伊达比星一起孵育。将DOX都还原成阿霉素（DOXOL），然后水解成糖苷配基DOX，然后
• Synthesis and antitumor activity of novel 4-demethoxyanthracyclines
  作者：Nigel Adams、Colin Blake、Michael J. Broadhurst、David J. Bushnell、Cedric H. Hassall、Hans R. Hartmann、Elizabeth Keech、Alan R. Stratton、Gareth J. Thomas

  DOI：10.1021/jm00171a010

  日期：1990.9

  A versatile and efficient synthetic route to 4-demethoxyanthracyclinones has been utilized in the preparation of a number of aglycons having 9-alkyl, 9-(hydroxylalkyl), or 9-carbamoyl substituents. Silver trifluoromethanesulfonate catalyzed coupling of these aglycons with various daunosamine derivatives has yielded a series of novel anthracyclines which have been evaluated as antitumor agents. 9-Alkylanthracyclines 22, 23, 33, and 34 have higher efficacy vs L-1210 leukemia than the parent 4-demethoxydaunorubicin (21), or the natural anthracyclines daunorubicin (1) and doxorubicin (2). 9-(Hydroxyalkyl) derivatives have in most cases high efficacy but are slightly less potent than 21. 9-Methyl analogue 22 has higher efficacy vs P388 leukemia than other anthracyclines tested, while 9-(hydroxymethyl) derivative 37 retains similar efficacy to anthracyclines 1, 2, and 21 but is considerably more potent. The N-substituted 9-carbamoylanthracyclines are devoid of antitumor activity.
• IDARUBICIN FOR THE TREATMENT OF LYMPHOMA IN A DOG
  申请人：Berlinski Pamela Jo

  公开号：US20100234314A1

  公开（公告）日：2010-09-16

  The present invention relates to a method of treating a lymphoma in a dog comprising administering to a dog in need of such treatment a therapeutically effective amount of idarubicin or a pharmaceutically acceptable salt thereof.
• [EN] IDARUBICIN FOR THE TREATMENT OF LYMPHOMA IN A DOG<br/>[FR] URADIBICINE UTILISÉE DANS LE TRAITEMENT DU LYMPHOME CHEZ UN CHIEN
  申请人：PFIZER PROD INC

  公开号：WO2009053804A2

  公开（公告）日：2009-04-30

  The present invention relates to a method of treating a lymphoma in a dog comprising administering to a dog in need of such treatment a therapeutically effective amount of idarubicin or a pharmaceutically acceptable salt thereof.