Stanozolol | 99996-65-3

• 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: Stanozolol
• 英文别名: 17beta-Hydroxy-5alpha-androstano[3,2-c]pyrazole；(1S,2S,10S,13R,14S,17S,18S)-2,18-dimethyl-6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-ol
• CAS: 99996-65-3
• 化学式: C₂₀H₃₀N₂O
• 分子量: 314.471
• InChiKey: GZCJWTCFQKPYQN-YNZDMMAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Stanozolol 在 吡啶 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (5α)-1'-(methylsulfonyl)-1'H-androstano<3,2-c>pyrazol-17-one
  参考文献：
  名称：

  Antiandrogenic steroidal sulfonylpyrazoles

  摘要：

  The steroidal sulfonylpyrazole 1 bound to the rat ventral prostate androgen receptor in vitro; it inhibited testosterone propionate induced increases in ventral prostate weight in vivo in the castrated, immature male rat with an ED50 of 15 mg/kg po. Compound 1 lacked androgenic activity in vivo in contrast to the parent steroidal pyrazole 5, which was both androgenic and antiandrogenic. The 2'- and 5'-methylsulfonyl isomers 6 and 6a did not bind to the androgen receptor. Introduction of an alkylsulfonyl at the N-1'-position has served, therefore, to isolate the intrinsic antiandrogenic properties of the steroidal heterocycle free of apparent hormone agonist properties. Structure-activity relationship studies revealed that a methylsulfonyl group at N-1' together with a C-17 alpha-substituent were the optimal combination for in vitro androgen receptor binding, in vivo antiandrogenic potency, and a lack of androgenic activity.

  DOI：

  10.1021/jm00170a008

文献信息

• DIHYDROTESTOSTERONE AND DIHYDROTESTOSTERONE DERIVATIVES AND PROMOTERS IN THE TREATMENT OF CANCER
  申请人：Tyme, Inc.

  公开号：US20170333451A1

  公开（公告）日：2017-11-23

  The present disclosure is directed to methods of treating cancer comprising administering dihydrotestosterone, a dihydrotestosterone derivative, a dihydrotestosterone promoter, or a combination thereof to a patient in need of treatment.
• Dihydrotestosterone and Dihydrotestosterone Derivatives and Promoters in the Treatment of Cancer
  申请人：Tyme, Inc.

  公开号：US20180193360A1

  公开（公告）日：2018-07-12

  The present disclosure is directed to methods of treating cancer comprising administering dihydrotestosterone, a dihydrotestosterone derivative, a dihydrotestosterone promoter, or a combination thereof to a patient in need of treatment.
• [EN] DIHYDROTESTOSTERONE AND DIHYDROTESTOSTERONE DERIVATIVES AND PROMOTERS IN THE TREATMENT OF CANCER<br/>[FR] DIHYDROTESTOSTÉRONE ET DÉRIVÉS DE DIHYDROTESTOSTÉRONE ET PROMOTEURS POUR LE TRAITEMENT DU CANCER
  申请人：TYME INC

  公开号：WO2017201217A1

  公开（公告）日：2017-11-23

  The present disclosure is directed to methods of treating cancer comprising administering dihydrotestosterone, a dihydrotestosterone derivative, a dihydrotestosterone promoter, or a combination thereof to a patient in need of treatment.
• Antiandrogenic steroidal sulfonylpyrazoles
  作者：Robert G. Christiansen、Malcolm R. Bell、Thomas E. D'Ambra、John P. Mallamo、John L. Herrmann、James H. Ackerman、Chester J. Opalka、Rudolph K. Kullnig、Richard C. Winneker

  DOI：10.1021/jm00170a008

  日期：1990.8

  The steroidal sulfonylpyrazole 1 bound to the rat ventral prostate androgen receptor in vitro; it inhibited testosterone propionate induced increases in ventral prostate weight in vivo in the castrated, immature male rat with an ED50 of 15 mg/kg po. Compound 1 lacked androgenic activity in vivo in contrast to the parent steroidal pyrazole 5, which was both androgenic and antiandrogenic. The 2'- and 5'-methylsulfonyl isomers 6 and 6a did not bind to the androgen receptor. Introduction of an alkylsulfonyl at the N-1'-position has served, therefore, to isolate the intrinsic antiandrogenic properties of the steroidal heterocycle free of apparent hormone agonist properties. Structure-activity relationship studies revealed that a methylsulfonyl group at N-1' together with a C-17 alpha-substituent were the optimal combination for in vitro androgen receptor binding, in vivo antiandrogenic potency, and a lack of androgenic activity.