?1-雄甾烯-3alpha,17beta-二醇 | 38859-38-0

• 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: ?1-雄甾烯-3alpha,17beta-二醇
• 中文别名: δ1-雄烯-3α，17β-二醇
• 英文名称: 5α-androst-1-ene-3α,17β-diol
• 英文别名: 5|A-Androst-1-ene-3|A,17|A-diol；(3S,5S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 38859-38-0
• 化学式: C₁₉H₃₀O₂
• 分子量: 290.446
• InChiKey: RZFGPAMUAXASRE-KHOSGYARSA-N

物化性质

• 沸点：
  418.0±38.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、乙醇（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ?1-雄甾烯-3alpha,17beta-二醇 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 1-睾酮
  参考文献：
  名称：

  Klein,U.; Sucrow,W., Chemische Berichte, 1977, vol. 110, p. 994 - 999

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羧基阿拉伯糖醇1-磷酸酯 在 N,N-二甲基乙酰胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 ?1-雄甾烯-3alpha,17beta-二醇
  参考文献：
  名称：

  Klein,U.; Sucrow,W., Chemische Berichte, 1977, vol. 110, p. 994 - 999

  摘要：

  DOI：

文献信息

• Bioavailable prodrugs of androgenic steroids and related method
  申请人：——

  公开号：US20020183532A1

  公开（公告）日：2002-12-05

  A compound for supplementing the concentration of a parent androgen in a subject in vivo, wherein the parent androgen has a skeletal structure including a 17 position and the parent androgen further has a 17&bgr;-hydroxy group comprising a 17&bgr;-hydroxy hydrogen appended to the 17 position. The compound comprises a substrate having the skeletal structure of the parent androgen including a 17 position corresponding to the 17 position of the parent androgen, and a promoiety comprising an alkoxymethyl ether appended to the 17 position of the substrate as a substitute for the 17&bgr;-hydroxy hydrogen. Related compounds and methods also are disclosed.

  一种用于补充体内受试者体内母体雄激素浓度的化合物，其中母体雄激素具有包括17位的骨架结构，母体雄激素进一步具有17&bgr;-羟基，该17&bgr;-羟基包括附加到17位的17&bgr;-羟基氢。该化合物包括具有母体雄激素骨架结构的底物，该底物包括与母体雄激素的 17 位相对应的 17 位，以及原基，该原基包括附着于底物 17 位的烷氧基甲基醚，作为 17&bgr;-hydroxy 氢的替代物。还公开了相关的化合物和方法。
• Composition and method for increasing in vivo androgen concentration
  申请人：——

  公开号：US20030134828A1

  公开（公告）日：2003-07-17

  A composition is provided including a first prohormone for increasing the concentration of a Class I parent androgen in a subject in vivo, and a second prohormone for increasing the concentration of a Class II parent androgen in the subject in vivo. The first prohormone includes a first carbon-carbon double bond at the 1 position, and a first 17&bgr;-hydroxy oxygen appended to the 17 position. The first prohormone further includes a first 17-position promoiety is appended to the first 17&bgr;-hydroxy oxygen as a substitute for the 17&bgr;-hydroxy hydrogen of the Class I parent androgen. The second prohormone includes a second carbon-carbon double bond at the 4 position and a second 17&bgr;-hydroxy oxygen appended to the 17 position. The second prohormone also includes a second 17-position promoiety appended to the second 17&bgr;-hydroxy oxygen as a substitute for the 17&bgr;-hydroxy hydrogen of the Class II parent androgen.

  提供了一种组合物，其中包括用于增加体内受试者体内第一类母体雄激素浓度的第一种原激素，以及用于增加体内受试者体内第二类母体雄激素浓度的第二种原激素。第一种原激素包括位于 1 位的第一碳碳双键，以及附加到 17 位的第一 17&bgr;-羟基氧。第一种原激素还包括与第一17&bgr;-羟基氧相连的第一17位原基，作为第一类母雄激素的17&bgr;-羟基氢的替代物。第二种原激素包括位于 4 位的第二个碳碳双键和附加到 17 位的第二个 17&bgr;-羟基氧。第二种原激素还包括与第二17&bgr;-羟基氧相连的第二17位原基，作为第二类母雄激素的17&bgr;-羟基氢的替代物。
• Pharmaceutical compositions and treatment methods - 8
  申请人：Ahlem Nathaniel Clarence

  公开号：US20050159366A1

  公开（公告）日：2005-07-21

  The invention provides compositions comprising formula 1 steroids, e.g., 16α-bromo-3β-hydroxy-5α-androstan-17-one hemihydrate and one or more excipients, typically wherein the composition comprises less than about 3% water. The compositions are useful to make improved pharmaceutical formulations. The invention also provides methods of intermittent dosing of steroid compounds such as analogs of 16α-bromo-3β-hydroxy-5α-androstan-17-one and compositions useful in such dosing regimens. The invention further provides compositions and methods to inhibit pathogen (viral) replication, ameliorate symptoms associated with immune dysregulation and to modulate immune responses in a subject using certain steroids and steroid analogs. The invention also provides methods to make and use these immunomodulatory compositions and formulations.

  本发明提供了由式 1 类固醇（如 16α-溴-3β-羟基-5α-雄甾烷-17-酮半水合物）和一种或多种赋形剂组成的组合物，其中组合物通常包含小于约 3% 的水。这些组合物可用于制造改良药物制剂。本发明还提供了类固醇化合物（如 16α-溴-3β-羟基-5α-雄甾烷-17-酮的类似物）的间歇给药方法和用于此类给药方案的组合物。本发明进一步提供了使用某些类固醇和类固醇类似物抑制病原体（病毒）复制、改善与免疫失调相关的症状和调节受试者免疫反应的组合物和方法。本发明还提供了制造和使用这些免疫调节组合物和制剂的方法。
• Pharmaceutical compositions and treatment methods-7
  申请人：Ahlem Nathaniel Clarence

  公开号：US20050282732A1

  公开（公告）日：2005-12-22

  The invention provides compositions comprising formula 1 steroids, e.g., 16α-bromo-3β-hydroxy-5α-androstan-17-one hemihydrate and one or more excipients, typically wherein the composition comprises less than about 3% water. The compositions are useful to make improved pharmaceutical formulations. The invention also provides methods of intermittent dosing of steroid compounds such as analogs of 16α-bromo-3β-hydroxy-5α-androstan-17-one and compositions useful in such dosing regimens. The invention further provides compositions and methods to inhibit pathogen (viral) replication, ameliorate symptoms associated with immune dysregulation and to modulate immune responses in a subject using certain steroids and steroid analogs. The invention also provides methods to make and use these immunomodulatory compositions and formulations.

  本发明提供了由式 1 类固醇（如 16α-溴-3β-羟基-5α-雄甾烷-17-酮半水合物）和一种或多种赋形剂组成的组合物，其中组合物通常包含小于约 3% 的水。这些组合物可用于制造改良药物制剂。本发明还提供了类固醇化合物（如 16α-溴-3β-羟基-5α-雄甾烷-17-酮的类似物）的间歇给药方法和用于此类给药方案的组合物。本发明进一步提供了使用某些类固醇和类固醇类似物抑制病原体（病毒）复制、改善与免疫失调相关的症状和调节受试者免疫反应的组合物和方法。本发明还提供了制造和使用这些免疫调节组合物和制剂的方法。
• Steroidal isomers with uniform mass spectra of their per-TMS derivatives: Synthesis of 17-hydroxyandrostan-3-ones, androst-1-, and -4-ene-3,17-diols
  作者：Maria K. Parr、Josef Zapp、Michael Becker、Georg Opfermann、Ulrike Bartz、Wilhelm Schänzer

  DOI：10.1016/j.steroids.2007.03.006

  日期：2007.6

  In human sports doping control analysis most of the steroids are analyzed after enzymatic hydrolysis of the glucuronides as per-trimethylsilyl (TMS) derivatives applying gas chromatography-mass spectrometry (GC-MS). According to the recommendations of the World Anti-Doping Agency the identification of analytes should be based on retention time and on mass spectrometric characterization. This study shows that the bis-TMS derivatives of 16 specific C19 steroids, namely the stereoisomers of S xi-androst-l-ene-3 xi,17 xi-diol (8 isomers), androst-4-ene-3 xi,17 xi-diol (4 isomers), and 17 xi-hydroxy-5 xi-androstan-3-one (4 isomers), reveal very similar mass spectra. As a rule, when taking the retention times, which are provided as Kovac indices for all these isomers, into account, a restriction to two or three possible isomers is possible. Reliable identification should additionally include a comparison of the retention times of the analytes with the reference compounds measured concomitantly. In some cases standard addition may be appropriate.Due to the limited availability; the above mentioned isomers were synthesized by reduction of the corresponding alpha,beta-unsaturated oxo, steroids either with K-Selectride or by catalytic hydrogenation (Pd/C as catalyst). The products of the reactions were identified by means of nuclear magnetic resonance (NMR) characterization and by further reduction to the corresponding 5 xi-androstane-3 xi,17 xi-diols and GC-MS comparison with commercially available reference standards. (c) 2007 Elsevier Inc. All rights reserved.