HE-3177 | 1001100-64-6

• 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: HE-3177
• 英文别名: 3β,7β,16α,17β-tetrahydroxyandrost-5-ene；androst-5-ene-3β,7β,16α,17β-tetrol；HE3177；3beta,7beta,16alpha,17beta-Tetrahydroxyandrost-5-ene；(3S,7R,8R,9S,10R,13S,14S,16R,17R)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7,16,17-tetrol
• CAS: 1001100-64-6
• 化学式: C₁₉H₃₀O₄
• 分子量: 322.445
• InChiKey: DBJXJRIEZQPLSN-WGNZAZMQSA-N

物化性质

• 熔点：
  229.1-231.4 °C
• 沸点：
  495.8±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]androst-5-ene-7,17-dione 在 盐酸 、 sodium tetrahydroborate 、 cerium(III) chloride 、 水 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 生成 HE-3177
  参考文献：
  名称：

  Novel components of the human metabolome: The identification, characterization and anti-inflammatory activity of two 5-androstene tetrols

  摘要：

  Two natural 5-androstene steroid tetrols, androst-5-ene-3 beta,7 beta,16 alpha,17 beta-tetrol (HE3177) and androst-5-ene-3 alpha,7 beta,16 alpha,17 beta-tetrol (HE3413), were discovered in human plasma and urine. These compounds had significant aqueous solubility, did not bind or transactivate steroid-binding nuclear hormone receptors. and were not immunosuppressive in murine mixed-lymphocyte studies. Both compounds appear to be metabolic end products, as they were resistant to primary and secondary metabolism. Both were orally bioavailable, and were very well tolerated in a two-week dose-intensive toxicity study in mice. Anti-inflammatory properties were found with exogenous administration of these compounds in rodent disease models of multiple sclerosis, lung injury, chronic prostatitis, and colitis. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.10.005

文献信息

• Compositions containing corticosteroids or analogues thereof and
  申请人：——

  公开号：US05387583A1

  公开（公告）日：1995-02-07

  3.beta.,17.beta.-androstenediol (".beta.AED") and 3.beta.,7.beta.,17.beta.-androstenetriol (".beta.AET") may be used to counteract the antiproliferative and immunosuppressive effects of hydrocortisone and other corticosteroids (i.e., to act as buffers to counteract the lymphosuppressive response to such steroids). .beta.AED and .beta.AET are steroids which mediate immune response to provide the body protection against immune down-regulation. A method for testing analogues of .beta.AED and .beta.AET to compare the effectiveness of such analogues as buffers of certain effects of hydrocortisone and other corticosteroids, including immune response and proliferative effects is described. Cytokines, including most particularly IL-3, are produced by addition of .beta.AET and .beta.AED and their analogues to the growth media of cell cultures of lymphatic cells.

  3.beta.,17.beta.-雄烯二醇（".beta.AED"）和3.beta.，7.beta.，17.beta.-雄烯三醇（".beta.AET"）可用于抵消氢化可的松和其他皮质类固醇的抗增殖和免疫抑制作用（即作为缓冲剂来抵消这些类固醇的淋巴抑制反应）。.beta.AED和.beta.AET是类固醇，介导免疫反应，为身体提供免疫下调保护。描述了一种测试.beta.AED和.beta.AET的类似物以比较这些类似物作为缓冲氢化可的松和其他皮质类固醇的某些效应（包括免疫反应和增殖效应）的有效性的方法。通过向淋巴细胞的细胞培养基中添加.beta.AET和.beta.AED及其类似物来产生细胞因子，包括尤其是IL-3。
• Drug Screen and Treatment Method
  申请人：Flores-Riveros Jaime

  公开号：US20080221074A1

  公开（公告）日：2008-09-11

  The invention relates to methods identify or characterize compounds that can be used to treat specified clinical disorders such as hyperglycemia and type 2 diabetes. Compounds that can be used in these methods include 4α-fluoro-17α-ethynylandrost-5-ene-3β,7β,17β-triol, 4α-fluoro-17α-ethynylandrost-5-ene-3β,7α,17β-triol, 4α-fluoro-17α-ethynylandrost-5-ene-3α,7β,17β-triol and 4α-fluoro-17α-ethynylandrost-5-ene-3β,17β-triol-7-one.

  本发明涉及用于治疗特定临床疾病，如高血糖和2型糖尿病的化合物的鉴定或表征方法。可以在这些方法中使用的化合物包括4α-氟-17α-乙炔基雄烯-5-烯-3β，7β，17β-三醇，4α-氟-17α-乙炔基雄烯-5-烯-3β，7α，17β-三醇，4α-氟-17α-乙炔基雄烯-5-烯-3α，7β，17β-三醇和4α-氟-17α-乙炔基雄烯-5-烯-3β，17β-三醇-7-酮。
• Drug Screening and Treatment Methods
  申请人：Flores-Riveros Jaime

  公开号：US20080146532A1

  公开（公告）日：2008-06-19

  The invention relates to methods identify or characterize compounds that can be used to treat specified clinical disorders such as hyperglycemia and type 2 diabetes. Compounds that can be used in these methods include 4α-fluoro-17α-ethynylandrost-5-ene-3β, 7β,17β-triol, 4α-fluoro-17α-ethynylandrost-5-ene-3β,7α,17β-triol, 4α-fluoro-17α-ethynylandrost-5-ene-3α,7β,17β-triol and 4α-fluoro-17α-ethynylandrost-5-ene-3β,17β-triol-7-one.

  本发明涉及一种用于识别或表征可用于治疗特定临床疾病如高血糖和2型糖尿病的化合物的方法。可用于这些方法的化合物包括4α-氟-17α-乙炔基雄烯-5-烯-3β,7β,17β-三醇，4α-氟-17α-乙炔基雄烯-5-烯-3β,7α,17β-三醇，4α-氟-17α-乙炔基雄烯-5-烯-3α,7β,17β-三醇和4α-氟-17α-乙炔基雄烯-5-烯-3β,17β-三醇-7-酮。
• Drug Identification and Treatment Method
  申请人：Frincke James M.

  公开号：US20080153792A1

  公开（公告）日：2008-06-26

  The invention relates to methods to identify compounds that can treat autoimmune conditions and treat specified clinical disorders such as multiple sclerosis, ulcerative colitis or arthritis. Compounds include 17α-ethynylandrost-5-ene-3β,15β,7α,17β-tetrol, 4α-acetoxy-17α-ethynylandrost-5-ene-3β,7β,17β-triol, 17α-ethynylandrost-5-ene-3β,4β,7α,17β-tetrol, 17α-ethynylandrost-5-ene-3α,4β,7α,17β-tetrol and 17α-ethynylandrost-5-ene-3α,4β,17β-triol-7-one.

  本发明涉及一种识别能够治疗自身免疫疾病和治疗特定临床疾病（如多发性硬化症、溃疡性结肠炎或关节炎）的化合物的方法。这些化合物包括17α-乙炔基雄烯-5-烯-3β,15β,7α,17β-四醇，4α-乙酰氧基-17α-乙炔基雄烯-5-烯-3β,7β,17β-三醇，17α-乙炔基雄烯-5-烯-3β,4β,7α,17β-四醇，17α-乙炔基雄烯-5-烯-3α,4β,7α,17β-四醇和17α-乙炔基雄烯-5-烯-3α,4β,17β-三醇-7-酮。
• Patient populations and treatment methods
  申请人：Flores-Riveros Jaime

  公开号：US20100075937A1

  公开（公告）日：2010-03-25

  The invention provides, inter alia, methods to treat, e.g., hyperglycemia or diabetes patients having two or more of a BMI of at least 28 or 29, a fasting insulin level of at least 4 μU/mL or at least 6 μU/mL and optionally (i) a serum MCP1 level of at least about 400 pg/mL or at least about 500 pg/mL. The treatment method includes administering 17α-ethynylandrost-5-ene-3β, 7β, 17β-triol and optionally another compound such as metformin or glyburide. Specific embodiments include use of 17α-ethynylandrost-5-ene-3β, 7β, 17β-triol for the treatment of hypercholesterolemia in a patient and a BMI of at least 28 or 29 and optionally hyperglycemia. In these embodiments, the patient will most preferably have a fasting insulin level of at least 4 μU/mL or at least 5 μU/mL.

  本发明提供了治疗高血糖或糖尿病患者的方法，其中患者至少具有以下两种特征之一：BMI至少为28或29，空腹胰岛素水平至少为4μU/mL或至少为6μU/mL，以及可选地（i）血清MCP1水平至少约为400pg/mL或至少约为500pg/mL。治疗方法包括给予17α-乙炔基雄烯-5-烯-3β，7β，17β-三醇和可选的另一化合物，例如二甲双胍或格列苯脲。具体实施例包括使用17α-乙炔基雄烯-5-烯-3β，7β，17β-三醇治疗具有BMI至少为28或29，可选地具有高血糖的患者的高胆固醇血症。在这些实施例中，患者最好具有至少4μU/mL或至少5μU/mL的空腹胰岛素水平。