地屈孕酮杂质 | 4243-74-7

• 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: 地屈孕酮杂质
• 英文名称: 20α-dihydro-dydrogesterone
• 英文别名: 20α-Hydroxy-9β,10α-pregna-4,6-dien-3-on；20α-Hydroxy-9β.10α-pregna-4.6-dien-3-on；Pregna-4,6-dien-3-one, 20-hydroxy-, (9beta,10alpha,20S)-；(8S,9R,10S,13S,14S,17S)-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 4243-74-7
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: IQPNZLYVKOVQGH-LBDMABOLSA-N

物化性质

• 熔点：
  199.5-201 °C
• 沸点：
  467.2±14.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  去氢孕酮 在 recombinant human aldo-keto reductase 1C₂ 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 乙腈 为溶剂， 生成 地屈孕酮杂质
  参考文献：
  名称：

  Expression of human aldo-keto reductase 1C2 in cell lines of peritoneal endometriosis: Potential implications in metabolism of progesterone and dydrogesterone and inhibition by progestins

  摘要：

  The human aldo-keto reductase AKR1C2 converts 5 alpha-dihydrotestosterone to the less active 3 alpha-androstanediol and has a minor 20-ketosteroid reductase activity that metabolises progesterone to 20 alpha-hydroxyprogesterone. AKR1C2 is expressed in different peripheral tissues, but its role in uterine diseases like endometriosis has not been studied in detail. Some progestins used for treatment of endometriosis inhibit AKR1C1 and AKR1C3, with unknown effects on AKR1C2. In this study we investigated expression of AKR1C2 in the model cell lines of peritoneal endometriosis, and examined the ability of recombinant AKR1C2 to metabolise progesterone and progestin dydrogesterone, as well as its potential inhibition by progestins. AKR1C2 is expressed in epithelial and stromal endometriotic cell lines at the mRNA level. The recombinant enzyme catalyses reduction of progesterone to 20 alpha-hydroxyprogesterone with a 10-fold lower catalytic efficiency than the major 20-ketosteroid reductase, AKR1C1. AKR1C2 also metabolises progestin dydrogesterone to its 20 alpha-dihydrodydrogesterone, with 8.6-fold higher catalytic efficiency than 5 alpha-dihydrotestosterone. Among the progestins that are currently used for treatment of endometriosis, dydrogesterone, medroxyprogesterone acetate and 20 alpha-dihydrodydrogesterone act as AKR1C2 inhibitors with low mu M K-i values in vitro. Their potential in vivo effects should be further studied. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jsbmb.2011.12.011

文献信息

• van Kamp,H., Recueil des Travaux Chimiques des Pays-Bas, 1965, vol. 84, p. 853 - 862
  作者：van Kamp,H.

  DOI：——

  日期：——
• Expression of human aldo-keto reductase 1C2 in cell lines of peritoneal endometriosis: Potential implications in metabolism of progesterone and dydrogesterone and inhibition by progestins
  作者：Nataša Beranič、Petra Brožič、Boris Brus、Izidor Sosič、Stanislav Gobec、Tea Lanišnik Rižner

  DOI：10.1016/j.jsbmb.2011.12.011

  日期：2012.5

  The human aldo-keto reductase AKR1C2 converts 5 alpha-dihydrotestosterone to the less active 3 alpha-androstanediol and has a minor 20-ketosteroid reductase activity that metabolises progesterone to 20 alpha-hydroxyprogesterone. AKR1C2 is expressed in different peripheral tissues, but its role in uterine diseases like endometriosis has not been studied in detail. Some progestins used for treatment of endometriosis inhibit AKR1C1 and AKR1C3, with unknown effects on AKR1C2. In this study we investigated expression of AKR1C2 in the model cell lines of peritoneal endometriosis, and examined the ability of recombinant AKR1C2 to metabolise progesterone and progestin dydrogesterone, as well as its potential inhibition by progestins. AKR1C2 is expressed in epithelial and stromal endometriotic cell lines at the mRNA level. The recombinant enzyme catalyses reduction of progesterone to 20 alpha-hydroxyprogesterone with a 10-fold lower catalytic efficiency than the major 20-ketosteroid reductase, AKR1C1. AKR1C2 also metabolises progestin dydrogesterone to its 20 alpha-dihydrodydrogesterone, with 8.6-fold higher catalytic efficiency than 5 alpha-dihydrotestosterone. Among the progestins that are currently used for treatment of endometriosis, dydrogesterone, medroxyprogesterone acetate and 20 alpha-dihydrodydrogesterone act as AKR1C2 inhibitors with low mu M K-i values in vitro. Their potential in vivo effects should be further studied. (C) 2011 Elsevier Ltd. All rights reserved.