(4aR,4bS,6aS,7S,9aS,9bS,11S,11aS)-11-羟基-4A,6A-二甲基-N-(2-甲基-2-丙基)-2-氧代-2,4A,4B,5,6,6A,7,8,9,9A,9B,10,11,11A-十四氢-1H-茚并[5,4-f]喹啉-7-甲酰胺 | 154387-62-9

• 物质功能分类: 有机原料 - 氨基化合物
• 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
• 中文名称: (4aR,4bS,6aS,7S,9aS,9bS,11S,11aS)-11-羟基-4A,6A-二甲基-N-(2-甲基-2-丙基)-2-氧代-2,4A,4B,5,6,6A,7,8,9,9A,9B,10,11,11A-十四氢-1H-茚并[5,4-f]喹啉-7-甲酰胺
• 中文别名: 度他雄胺杂质16
• 英文名称: 6α-hydroxy-finasteride
• 英文别名: 6alpha-Hydroxyfinasteride；(1S,3aS,3bS,5S,5aS,9aR,9bS,11aS)-N-tert-butyl-5-hydroxy-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
• CAS: 154387-62-9
• 化学式: C₂₃H₃₆N₂O₃
• 分子量: 388.55
• InChiKey: VRADRJBKILTRPZ-XLGSXJLYSA-N

物化性质

• 沸点：
  616.0±55.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  非那雄胺 在 recombinant cytochrome P₄₅₀ 2D₆ 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 aq. phosphate buffer 为溶剂， 反应 1.0h， 生成 (4aR,4bS,6aS,7S,9aS,9bS,11S,11aS)-11-羟基-4A,6A-二甲基-N-(2-甲基-2-丙基)-2-氧代-2,4A,4B,5,6,6A,7,8,9,9A,9B,10,11,11A-十四氢-1H-茚并[5,4-f]喹啉-7-甲酰胺
  参考文献：
  名称：

  High-resolution mass spectrometric investigation of the phase I and II metabolites of finasteride in pig plasma, urine and bile

  摘要：

  1. The metabolite profile of the 5 alpha-reductase type II inhibitor finasteride has been studied in pig plasma, urine and bile using high-resolution mass spectrometry. The porcine biotransformation products were compared to those formed by human liver microsomes and to literature data of recently identified human in vivo metabolites. The objective of this study was to gain further evidence for the validity of using pigs for advanced, invasive drug-drug interaction studies that are not possible to perform in humans.2. The use of high-resolution mass spectrometry with accurate mass measurements enabled identification of the metabolites by calculation of their elemental compositions as well as their fragmentation patterns.3. There was an excellent match between the porcine and human metabolic profiles, corroborating the pig as a model of human drug metabolism. The glucuronides of the two recently described human hydroxylated metabolites MX and MY and the carboxylated metabolite M3 were identified as the major biotransformation products of finasteride in pig urine and bile.4. Furthermore, the CYP enzymes involved in the formation of the hydroxylated metabolites were characterized. Human recombinant CYP3A4 could produce the two major hydroxylated metabolites MX and MY, whereas human recombinant CYP2D6 formed MY only.

  DOI：

  10.3109/00498254.2013.866298

文献信息

• High-resolution mass spectrometric investigation of the phase I and II metabolites of finasteride in pig plasma, urine and bile
  作者：Anna Lundahl、Annica Tevell Åberg、Ulf Bondesson、Hans Lennernäs、Mikael Hedeland

  DOI：10.3109/00498254.2013.866298

  日期：2014.6

  1. The metabolite profile of the 5 alpha-reductase type II inhibitor finasteride has been studied in pig plasma, urine and bile using high-resolution mass spectrometry. The porcine biotransformation products were compared to those formed by human liver microsomes and to literature data of recently identified human in vivo metabolites. The objective of this study was to gain further evidence for the validity of using pigs for advanced, invasive drug-drug interaction studies that are not possible to perform in humans.2. The use of high-resolution mass spectrometry with accurate mass measurements enabled identification of the metabolites by calculation of their elemental compositions as well as their fragmentation patterns.3. There was an excellent match between the porcine and human metabolic profiles, corroborating the pig as a model of human drug metabolism. The glucuronides of the two recently described human hydroxylated metabolites MX and MY and the carboxylated metabolite M3 were identified as the major biotransformation products of finasteride in pig urine and bile.4. Furthermore, the CYP enzymes involved in the formation of the hydroxylated metabolites were characterized. Human recombinant CYP3A4 could produce the two major hydroxylated metabolites MX and MY, whereas human recombinant CYP2D6 formed MY only.