6-羟基倍他米松 | 24703-00-2

• 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: 6-羟基倍他米松
• 英文名称: 6β-hydroxybetamethasone
• 英文别名: 6-Hydroxybetamethasone；(6R,8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-6,11,17-trihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
• CAS: 24703-00-2
• 化学式: C₂₂H₂₉FO₆
• 分子量: 408.467
• InChiKey: RVBSTEHLLHXILB-DNVCMXBESA-N

物化性质

• 熔点：
  >248°C (dec.)
• 沸点：
  613.2±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（轻微，超声处理）、DMSO（轻微）、甲醇（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  倍他米松二丙酸酯 在 phosphate buffer 、 air 、 plasma of 20 d pregnant Sprague-Dawley rat 作用下， 反应 1.0h， 以67.8%的产率得到9-氟-11beta,17,21-三羟基-16beta-甲基孕甾-1,4-二烯-3,20-二酮 17-丙酸酯
  参考文献：
  名称：

  Correlation between metabolism of betamethasone 17,21-dipropionate and adrenal hypertrophy in rat fetuses

  摘要：

  The effects of metabolites of betamethasone 17,21-dipropionate (BMDP) on the hypothalamo-pituitary-adrenocortical axis were assessed by measurements of adrenal weights, after studying the metabolism of BMDP in vivo and in vitro in pregnant rats and mice. After BMDP was injected intravenously at a dose of 5 mg/kg into rats and mice in late stages of pregnancy, it disappeared rapidly from the plasma and brain stages of pregnancy, it disappeared rapidly from the plasma and brain in both mothers and fetuses while betamethasone 17-propionate (BMP) was detected as the main metabolite followed by betamethasone (BM). In vitro studies demonstrated that BMDP was metabolized to BMP in maternal and fetal tissues (plasma, liver, brain and placenta) of both species. The subcutaneous administration of BMP to rats in the late stages of pregnancy induced adrenal hypertrophy in fetuses, though the adrenals of the mothers became atrophic. In the case of mice, both maternal and fetal adrenals became atrophic. Administration of BM produced adrenal atrophy in mothers and fetuses of both species. The subcutaneous administration of 6 beta-hydroxybetamethasone 17-propionate (6 beta-OH-BMP) to rat fetuses in utero produced adrenal hypertrophy and 6 beta-hydroxybetamethasone (6 beta-OH-BM) showed no effect. These data suggest that BMP is transferred across the placental barrier to produce marked adrenal hypertrophy in rat fetuses.

  DOI：

  10.1016/s0039-128x(81)90348-2

文献信息

• Correlation between metabolism of betamethasone 17,21-dipropionate and adrenal hypertrophy in rat fetuses
  作者：Masayuki Nakano、Masanori Nishiuchi、Masaharu Takeuchi、Hideo Yamada

  DOI：10.1016/s0039-128x(81)90348-2

  日期：1981.5

  The effects of metabolites of betamethasone 17,21-dipropionate (BMDP) on the hypothalamo-pituitary-adrenocortical axis were assessed by measurements of adrenal weights, after studying the metabolism of BMDP in vivo and in vitro in pregnant rats and mice. After BMDP was injected intravenously at a dose of 5 mg/kg into rats and mice in late stages of pregnancy, it disappeared rapidly from the plasma and brain stages of pregnancy, it disappeared rapidly from the plasma and brain in both mothers and fetuses while betamethasone 17-propionate (BMP) was detected as the main metabolite followed by betamethasone (BM). In vitro studies demonstrated that BMDP was metabolized to BMP in maternal and fetal tissues (plasma, liver, brain and placenta) of both species. The subcutaneous administration of BMP to rats in the late stages of pregnancy induced adrenal hypertrophy in fetuses, though the adrenals of the mothers became atrophic. In the case of mice, both maternal and fetal adrenals became atrophic. Administration of BM produced adrenal atrophy in mothers and fetuses of both species. The subcutaneous administration of 6 beta-hydroxybetamethasone 17-propionate (6 beta-OH-BMP) to rat fetuses in utero produced adrenal hypertrophy and 6 beta-hydroxybetamethasone (6 beta-OH-BM) showed no effect. These data suggest that BMP is transferred across the placental barrier to produce marked adrenal hypertrophy in rat fetuses.