5α-<3α,11,11,20β-2H4>pregnane-3β,20α-diol 20-acetate | 58718-33-5

• 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: 5α-<3α,11,11,20β-2H4>pregnane-3β,20α-diol 20-acetate
• CAS: 58718-33-5
• 化学式: C₂₃H₃₈O₃
• 分子量: 366.521
• InChiKey: GQXZPRCPDHVBKD-ZXEKVLBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5α-<3α,11,11,20β-2H4>pregnane-3β,20α-diol 20-acetate 在 碳酸氢钠 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.0h， 生成 5α-<3β,11,11,20β-2H4>pregnane-3α,20α-diol 20-acetate
  参考文献：
  名称：

  Stable isotope studies on steroid metabolism and kinetics: sulfates of 3α-hydroxy-5α-pregnane derivatives in human pregnancy

  摘要：

  The metabolism and production rates of 3-alpha-hydroxy-5-alpha-pregnane-20-one sulfate and the 3-sulfate and 3,20-disulfate of 5-alpha-pregnane-3-alpha, 20-alpha-diol in pregnant women were studied. The steroid sulfates were labeled with deuterium in the 3-beta, 11, 11- or 3-beta, 11, 11, 20-beta-positions and were injected intravenously. The deuterium content of steroid in the monosulfate and disulfate fraction of plasma collected at different times after the injection was determined by capillary column gas chromatography/mass spectrometry. The injected steroid sulfates underwent oxidoreduction at C-20 and 16-alpha-hydroxylation. In addition, the 3-sulfate of 5-alpha-pregnane-3-alpha, 20-alpha-diol became hydroxylated at C-21. The pregnanediol and pregnanetriol monosulfates were also converted to disulfates. No evidence was obtained for a metabolic sequence involving hydrolysis, oxidoreduction, and resulfation at the C-3 position. Production rates and rates of metabolic transformations were determined using different one-and two-pool models. The production rate of the pregnanolone/pregnanediol monosulfate couple was 0.08 to 0.5-mu-mol/24 h, the variability probably depending both on individual factors and stage of pregnancy. The half-life time for oxidation and reduction at C-20 was 0.1 to 0.4 hours, reduction being the faster process. The half-life time for the turnover of the steroid skeleton was 1.3 to 3.3 hours. The injected steroid monosulfates were 16-alpha-hydroxylated at a rate of 1 to 8-mu-mol/24 h. A significant fraction of these 16-alpha-hydroxylated steroid sulfates, 0.5 to 25-mu-mol/24 h, was formed from other, probably unconjugated, precursors. The 16-alpha-hydroxylated steroid monosulfates underwent rapid oxidoreduction at C-20. The 3-sulfate of 5-alpha-pregnane-3-alpha, 20-alpha-diol was hydroxylated at C-21. The production rate of 5-alpha-pregnane-3-alpha, 20-alpha, 21-triol 3-sulfate was 8 to 36-mu-mol/24 h in four women and 180-mu-mol/24 h in one woman, and this steroid was not formed from other precursors to a significant extent. 5-alpha-Pregnane-3-alpha, 20-alpha-diol disulfate was a metabolic end product accounting for a major part of the elimination of the steroids injected. Its half-life time was 1.4 to 2.8 hours. The results show that the formation of sulfated steroids with a 3-alpha-hydroxy-5-alpha configuration may account for 50% of the metabolism of progesterone in late pregnancy.

  DOI：

  10.1016/0039-128x(90)90013-2