17-beta-羟基雄甾-4-烯-3-酮烟酸酯 | 668-56-4

• 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: 17-beta-羟基雄甾-4-烯-3-酮烟酸酯
• 中文别名: 烟酸睾酮
• 英文名称: androst-4-en-3-on-17β-yl nicotinate
• 英文别名: testosterone-17β-nicotinate；testosterone nicotinate；[(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] pyridine-3-carboxylate
• CAS: 668-56-4
• 化学式: C₂₅H₃₁NO₃
• 分子量: 393.526
• InChiKey: KHRRLLSDLVLEIT-BKWLFHPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  17-beta-羟基雄甾-4-烯-3-酮烟酸酯 在 sodium dithionite 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 0.33h， 生成 17β-<(1,4-dihydro-1-methyl-3-pyridinylcarbonyl)oxy>androst-4-en-3-one
  参考文献：
  名称：

  通过生物膜XIV改善递送：使用氧化还原化学递送系统，特定于大脑的睾丸激素持续递送

  摘要：

  平衡吡啶鎓盐氧化还原递送系统中的二氢吡啶用于脑中睾丸激素的特异性递送和持续释放。在雌性大鼠中施用睾丸激素的N-甲基-1,4-二氢烟酸酯使大脑中相应的季铵盐，睾丸激素三扁桃酸酯高水平且持续存在。与此形成鲜明对比的是，它被迅速从普通流通中排除。随着季盐持续释放，睾丸激素“锁定”在大脑中，t1 / 2 = 20小时。

  DOI：

  10.1002/jps.2600730324
• 作为产物：
  描述：

  烟酸 在 氯化亚砜 作用下， 以 吡啶 为溶剂， 反应 7.0h， 生成 17-beta-羟基雄甾-4-烯-3-酮烟酸酯
  参考文献：
  名称：

  通过生物膜XIV改善递送：使用氧化还原化学递送系统，特定于大脑的睾丸激素持续递送

  摘要：

  平衡吡啶鎓盐氧化还原递送系统中的二氢吡啶用于脑中睾丸激素的特异性递送和持续释放。在雌性大鼠中施用睾丸激素的N-甲基-1,4-二氢烟酸酯使大脑中相应的季铵盐，睾丸激素三扁桃酸酯高水平且持续存在。与此形成鲜明对比的是，它被迅速从普通流通中排除。随着季盐持续释放，睾丸激素“锁定”在大脑中，t1 / 2 = 20小时。

  DOI：

  10.1002/jps.2600730324

文献信息

• Brain-specific drug delivery
  申请人：University of Florida

  公开号：US04824850A1

  公开（公告）日：1989-04-25

  The subject compounds, which are adapted for the site-specific/sustained delivery of centrally acting drug species to the brain, are: (a) compounds of the formula [D--DHC] (I) wherein [D] is a centrally acting drug species, and [DHC] is the reduced, biooxidizable, blood-brain barrier penetrating lipoidal form of a dihydropyridine.revreaction.pyridinium salt redox carrier, with the proviso that when [DHC] is ##STR1## wherein R is lower alkyl or benzyl and [D] is a drug species containing a single NH.sub.2 or OH functional group, the single OH group when present being a primary or secondary OH group, said drug species being linked directly through said NH.sub.2 or OH function group to the carbonyl function of [DHC], then [D] must be other than a sympathetic stimulant, steroid sex hormone or long chain alkanol; and (b) non-toxic pharmaceutically acceptable salts of compounds of formula (I) wherein [D] is a centrally acting drug species and [DHC] is the reduced, biooxidizable, blood-brain barrier penetrating lipoidal form of a dihydropyridine.revreaction.pyridinium salt redox carrier. The corresponding ionic pyridinium salt type drug/carrier entitles [D--QC].sup.+ X.sup.- are also disclosed.

  这些适用于将中枢作用药物种类定向/持续释放到大脑的主体化合物是：(a) 公式[D--DHC] (I)的化合物，其中[D]是中枢作用药物种类，[DHC]是二氢吡啶盐氧化还原、穿透血脑屏障的脂质形式，带有二氢吡啶盐氧化还原载体，但当[DHC]是##STR1##其中R是较低的烷基或苄基，[D]是含有单个NH.sub.2或OH官能团的药物种类，当存在单个OH官能团时，该OH官能团为一次或二次OH官能团，该药物种类通过NH.sub.2或OH官能团直接连接到[DHC]的羰基官能团，则[D]不能是交感神经刺激剂、类固醇性激素或长链烷醇；以及(b) 公式(I)的化合物的无毒的药用可接受盐，其中[D]是中枢作用药物种类，[DHC]是二氢吡啶盐氧化还原、穿透血脑屏障的脂质形式，带有二氢吡啶盐氧化还原载体。还披露了相应的离子式吡啶盐型药物/载体[D--QC].sup.+ X.sup.-。
• Technology for the Preparation of Microparticles
  申请人：Malakhov Michael

  公开号：US20090098207A1

  公开（公告）日：2009-04-16

  Microspheres are produced by contacting a solution of a macromolecule or small molecule in a solvent with an antisolvent and a counterion, and chilling the solution. The microspheres are useful for preparing pharmaceuticals, nutraceuticals, cosmetic products and the like of defined dimensions.

  微球是通过将溶液中的大分子或小分子与抗溶剂和对离子接触，并冷却溶液而制备的。这些微球可用于制备具有明确定义尺寸的药物、营养保健品、化妆品等产品。
• Testicular-specific drug delivery
  申请人：University of Florida

  公开号：US04622218A1

  公开（公告）日：1986-11-11

  Testicularly acting drug species are site-specifically/sustainedly delivered to the testes by administering to a male in need of such treatment a pharmacologically effective amount of the target drug species [D] tethered to a reduced, blood-testis barrier penetrating lipoidal form [D--DHC] of a dihydropyridine.revreaction.pyridinium salt type redox carrier, e.g. 1,4-dihydrotrigonelline. Oxidation of the dihydropyridine carrier moiety in vivo to the ionic pyridinium salt type drug/carrier entity [D--QC].sup.+ prevents elimination thereof from the testes, while elimination from the general circulation is accelerated, resulting in significant and prolongedly sustained testicular-specific drug activity, whether ascribable to the cleavage of the [D--QC].sup.+ entity and sustained release of the drug [D] in the testes and/or to [D--QC].sup.+ itself.

  睾丸作用药物种类通过给需要此类治疗的男性施用目标药物种类[D]的药理有效量，将其定向/持续地传递到睾丸。所使用的是一种还原的、穿透血睾障壁的脂质形式[D--DHC]的二氢吡啶.叠氮盐型氧化还原载体，例如1,4-二氢三甲基咖啡碱。体内二氢吡啶载体基团氧化为离子型叠氮盐型药物/载体实体[D--QC].sup.+，防止其从睾丸中被排除，同时加速其从一般循环中的排除，导致显著且持续时间较长的睾丸特异性药物活性，无论是归因于[D--QC].sup.+实体的裂解和药物[D]在睾丸中的持续释放，还是[D--QC].sup.+本身。
• Transdermal Delivery of Therapeutic Agents Using Poly (Amidoamine) Dendrimers
  申请人：UNIVERSITY OF ILLINOIS CHICAGO

  公开号：US20140018435A1

  公开（公告）日：2014-01-16

  The invention provides for compositions for transdermal delivery of a therapeutic agent associated with a surface modified poly(amidoamine) PAMAM dendrimer, wherein the surface modified dendrimer increased skin penetration of the therapeutic agent. The invention particularly provides for compositions and methods for transdermal delivery of anticancer and chemo-preventive agents.

  本发明提供了一种与表面修饰的聚酰胺胺（PAMAM）树状分子相关的治疗剂经皮递送的组合物，其中表面修饰的树状分子增加了治疗剂的皮肤渗透性。本发明特别提供了用于经皮递送抗癌和化学预防剂的组合物和方法。
• Androstanes as androgen receptor modulators
  申请人：——

  公开号：US20040235808A1

  公开（公告）日：2004-11-25

  Compounds of structural formula (I) as herein defined are disclosed as useful in a method for modulating a function of the androgen receptor in a tissue selective manner in a patient in need of such modulation, as well as in a method of activating the function of the androgen receptor in a patient, and in particular the method wherein the function of the androgen receptor is blocked in the prostate of a male patient or in the uterus of a female patient and activated in bone and/or muscle tissue. These compounds are useful in the treatment of conditions caused by androgen deficiency or which can be ameliorated by androgen administration, including osteopenia, osteoporosis, periodontal disease, bone fracture, bone damage following bone reconstructive surgery, sarcopenia, frailty, aging skin, male hypogonadism, female sexual dysfunction, postmenopausal symptoms in women, atherosclerosis, hypercholesterolemia, hyperlipidemia, aplastic anemia and other hematopoietic disorders, pancreatic cancer, renal cancer, prostate cancer, inflammatory arthritis and joint repair, alone or in combination with other active agents.

  本文所定义的结构式（I）的化合物被披露为在患者中以组织选择性的方式调节雄激素受体功能的方法中有用，以及在患者中激活雄激素受体功能的方法，特别是在男性患者的前列腺或女性患者的子宫中阻止雄激素受体功能并在骨骼和/或肌肉组织中激活雄激素受体功能的方法。这些化合物在治疗由雄激素缺乏引起或可以通过雄激素治疗改善的疾病中有用，包括骨质疏松症、骨质疏松、牙周病、骨折、骨重建手术后的骨损伤、肌肉萎缩、虚弱、老化皮肤、男性性腺功能减退、女性性功能障碍、绝经后妇女的症状、动脉硬化、高胆固醇血症、高脂血症、再生障碍性贫血和其他造血系统疾病、胰腺癌、肾癌、前列腺癌、炎性关节炎和关节修复，单独或与其他活性药物联合使用。