2alpha-(Hydroxymethyl)-17-methyl-5alpha-androstane-3beta,17beta-diol | 6945-91-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 2alpha-(Hydroxymethyl)-17-methyl-5alpha-androstane-3beta,17beta-diol
• 英文别名: (2S,3R,5S,8R,9S,10S,13S,14S,17S)-2-(hydroxymethyl)-10,13,17-trimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 6945-91-1
• 化学式: C₂₁H₃₆O₃
• 分子量: 336.515
• InChiKey: FJEQNAVGFPKKSD-KWHXHVTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  oxymetholone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 、 2alpha-(Hydroxymethyl)-17-methyl-5alpha-androstane-3beta,17beta-diol 、 17β-hydroxy-2α-hydroxymethyl-17α-methyl-5α-androstan-3-one
  参考文献：
  名称：

  Identification of drostanolone and 17-methyldrostanolone metabolites produced by cryopreserved human hepatocytes

  摘要：

  Methyldrostanolone (2 alpha,17 alpha-dimethyl-17 beta-hydroxy-5 alpha-androstan-3-one) was synthesized from drostanolone (17 beta-hydroxy-2 alpha-methyl-5 alpha-androstan-3-one) and identified in commercial products. Cultures of cryopreserved human hepatocytes were used to study the biotransformation of drostanolone and its 17-methylated derivative. For both steroids, the common 3 alpha-(major) and 3 beta-reduced metabolites were identified by GC-MS analysis of the extracted culture medium and the stereochemistry confirmed by incubation with 3 alpha-hydroxysteroid dehydrogenase. Structures corresponding to hydroxylated metabolites in C-12 (minor) and C-16 were proposed for other metabolites based upon the evaluation of the mass spectra of the pertrimethylsilyl (TMS-d(0) and TMS-d(9)) derivatives. Finally, on the basis of the GC-MS and H-1 NMR data and through chemical synthesis of the 17-methylated model compounds, structures could be proposed for metabolites hydroxylated in C-2. All the metabolites extracted from hepatocyte culture medium were present although in different relative amounts in urines collected following the administration to a human volunteer. therefore confirming the suitability of the cryopreserved hepatocytes to generate characteristic metabolites and study biotransformation of new steroids. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.11.002

文献信息

• Identification of drostanolone and 17-methyldrostanolone metabolites produced by cryopreserved human hepatocytes
  作者：Julie Gauthier、Danielle Goudreault、Donald Poirier、Christiane Ayotte

  DOI：10.1016/j.steroids.2008.11.002

  日期：2009.3

  Methyldrostanolone (2 alpha,17 alpha-dimethyl-17 beta-hydroxy-5 alpha-androstan-3-one) was synthesized from drostanolone (17 beta-hydroxy-2 alpha-methyl-5 alpha-androstan-3-one) and identified in commercial products. Cultures of cryopreserved human hepatocytes were used to study the biotransformation of drostanolone and its 17-methylated derivative. For both steroids, the common 3 alpha-(major) and 3 beta-reduced metabolites were identified by GC-MS analysis of the extracted culture medium and the stereochemistry confirmed by incubation with 3 alpha-hydroxysteroid dehydrogenase. Structures corresponding to hydroxylated metabolites in C-12 (minor) and C-16 were proposed for other metabolites based upon the evaluation of the mass spectra of the pertrimethylsilyl (TMS-d(0) and TMS-d(9)) derivatives. Finally, on the basis of the GC-MS and H-1 NMR data and through chemical synthesis of the 17-methylated model compounds, structures could be proposed for metabolites hydroxylated in C-2. All the metabolites extracted from hepatocyte culture medium were present although in different relative amounts in urines collected following the administration to a human volunteer. therefore confirming the suitability of the cryopreserved hepatocytes to generate characteristic metabolites and study biotransformation of new steroids. (C) 2008 Elsevier Inc. All rights reserved.