(17βH)-pregn-4-en-20-yno[2,3-d]isoxazol-17-ol | 17230-88-5

• 物质功能分类: 原料药 - 激素及调节内分泌功能类药 - 雄激素及同化激素类药
• 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: (17βH)-pregn-4-en-20-yno[2,3-d]isoxazol-17-ol
• 英文别名: 17α-pregna-2,4-dien-20-yno[2,3-d]-isoxazol-17β-ol；danazol；Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol, (17alpha)-；(2R,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-trien-17-ol
• CAS: 17230-88-5
• 化学式: C₂₂H₂₇NO₂
• 分子量: 337.462
• InChiKey: POZRVZJJTULAOH-GSQPBCFPSA-N

物化性质

• 熔点：
  224.4-226.80C
• 比旋光度：
  D25 +7.5° (ethanol); D25 +21.9° (chloroform)
• 沸点：
  473.76°C (rough estimate)
• 密度：
  1.0909 (rough estimate)
• 溶解度：
  可溶于乙腈（少许）、氯仿（少许）、乙醇（少许）、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S36
• 危险类别码：
  R20/21/22,R63
• WGK Germany：
  3
• 海关编码：
  2937290014
• RTECS号：
  TU4157070

制备方法与用途

达那唑（Danazol）简介

达那唑是一种用于治疗子宫内膜异位症、乳腺小叶增生、遗传性血管性水肿及其他疾病的药物，主要通过口服给药。

不良反应

达那唑的主要不良反应包括痤疮、水肿、多毛、声粗、乳房变小、体重增加、皮肤或毛发油腻感、头痛以及肝功能障碍等。大多数女性会出现闭经现象，少数人可能出现不规则阴道出血。

药理作用

达那唑是一种合成的17α-乙炔睾酮衍生物，属于弱雄激素类药物，没有孕激素和雌激素活性。它具有促性腺激素抑制作用，并兼有蛋白质同化及抗孕激素作用。该药物通过作用于下丘脑-垂体-卵巢轴，抑制促性腺激素的分泌与释放，从而减少卵泡刺激素和黄体生成素的释放；直接抑制卵巢甾体激素的生成，使体内雌激素水平下降，进而抑制子宫内膜及异位子宫内膜组织生长，使其失活萎缩，导致不排卵及闭经。这种作用可持续6～8个月。此外，达那唑还能消除纤维性乳腺炎结节、减轻疼痛和触痛，但可能诱发月经失调或闭经，这与其减少雌激素有关。同时，它还能提高血清C1酯酶抑制物水平，导致补体系统中C4浓度升高。

适应症

达那唑用于治疗子宫内膜异位症、纤维性乳腺炎、男性乳房发育、乳腺痛、痛经、腹痛等病症，还适用于性早熟、原发性血小板减少性紫癜、血友病和Christmas病、遗传性血管性水肿以及系统性红斑狼疮的治疗。

生物活性

达那唑是合成类固醇Ethisterone的衍生物，能够抑制促性腺激素产生，并具有一定的弱雄激素作用。主要用于子宫内膜异位症和自发性血小板减少症的治疗。

文献信息

• Method for treatment of diseases
  申请人：Ampio Pharmaceuticals, Inc.

  公开号：EP2554174B1

  公开（公告）日：2015-09-02
• "METHODS AND PRODUCTS FOR TREATMENT OF DISEASES"
  申请人：Bar-Or David

  公开号：US20070111972A1

  公开（公告）日：2007-05-17

  The present invention relates to the treatment of diseases and conditions with an effective amount of a steroid having those formulas given in the specification, or a pharmacologically-acceptable salt or ester thereof. The disease or conditions treatable according to the invention include angiogenic diseases and conditions of the eye, angiogenic diseases and conditions of the brain, inflammatory diseases and conditions of the eye, inflammatory diseases and conditions of the brain and neurodegenerative diseases.
• METHODS AND PRODUCTS FOR TREATMENT OF DISEASES
  申请人：Bar-Or David

  公开号：US20100323991A1

  公开（公告）日：2010-12-23

  The invention provides a method of treating a disease or condition mediated by vascular hyperpermeability in an animal. The method comprises administering an amount of a danazol compound effective to inhibit vascular hyperpermeability and an amount of a second drug effective to treat the disease or condition. The invention further provides a method of inhibiting vascular hyperpermeability when it is a side effect caused by administration of a drug to, or another treatment of, an animal. The method comprises administration of an amount of a danazol compound effective to inhibit the vascular hyperpermeability. The invention also provides a method of modulating the cytoskeleton of endothelial cells in an animal comprising administering an amount of a danazol compound and an amount of a second drug effective to modulate the cytoskeleton. The present invention also relates to pharmaceutical compositions and kits comprising a danazol compound and a second drug.
• METHOD FOR TREATMENT OF DISEASES
  申请人：Bar-Or David

  公开号：US20100324005A1

  公开（公告）日：2010-12-23

  The invention provides a method of inhibiting vascular hyperpermeability in an animal in need thereof. The method comprises administering a vascular-hyperpermeability-inhibiting amount of a danazol compound to the animal. The invention also provides a method of modulating the cytoskeleton of an endothelial cell in an animal. The method comprises administering an effective amount of a danazol compound to the animal.
• METHODS OF TREATMENT OF DISEASES
  申请人：Ampio Pharmaceuticals, Inc.

  公开号：US20140227347A1

  公开（公告）日：2014-08-14

  The invention provides a method of inhibiting vascular hyperpermeability in an animal in need thereof. The method comprises administering a vascular-hyperpermeability-inhibiting amount of a danazol compound to the animal. The method comprises administering an effective amount of a danazol compound to the animal accounting for the body fat content of the animal. The invention also provides a method of modulating the cytoskeleton of an endothelial cell in an animal.