睾酮 | 1221910-14-0

• 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: 睾酮
• 英文名称: 17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
• 英文别名: testosterone；17-Hydroxyandrost-4-en-3-one；17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 1221910-14-0
• 化学式: C₁₉H₂₈O₂
• mdl: MFCD00411527
• 分子量: 288.43
• InChiKey: MUMGGOZAMZWBJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  432.9±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

毒理性

• 在妊娠和哺乳期间的影响

哺乳期使用概述：有限的数据表明，给哺乳期母亲皮下植入低剂量（100毫克）的睾酮药丸，似乎不会显著增加乳汁中的睾酮水平。然而，睾酮的口服生物利用度较低，因为首次通过肝脏代谢广泛，所以它似乎不会增加哺乳婴儿的血清睾酮水平。哺乳婴儿似乎不会受到母体或跨性别父体睾酮治疗的负面影响。高剂量的睾酮可以抑制泌乳。 对哺乳婴儿的影响：在产后母亲皮下植入100毫克睾酮药丸后，她的婴儿（年龄未说明）被哺乳（程度未说明）。在5个月的时间里，婴儿没有出现不良反应。 一名跨性别男性在分娩后13.75个月开始每周接受50毫克的睾酮环戊丙酸酯。1个月后，剂量增加到每周80毫克。他的男婴部分时间接受“胸部喂养”（程度未说明），直到婴儿在开始使用睾酮后的137天（18个月大）自行断奶。在此期间，婴儿的儿科医生没有注意到任何不良事件或男性化的迹象。婴儿正常生长和发育。 对泌乳和乳汁的影响：无论是来自肿瘤还是外源性给予的睾酮，超生理水平的睾酮都会减少产后女性的乳汁产量。睾酮本身会降低血清催乳素水平；然而，当与雌激素和黄体酮联合使用时，血清催乳素水平并没有明显降低。过去，睾酮曾作为一种治疗手段用来抑制泌乳，通常与雌激素联合使用。

◉ Summary of Use during Lactation:Limited data indicate that a low-dose (100 mg) subcutaneous testosterone pellet given to a nursing mother appears not to increase milk testosterone levels markedly. Subcutaneous testosterone cypionate does increase milk testosterone levels. However, testosterone has low oral bioavailability because of extensive first-pass metabolism, so it appears to not increase serum testosterone levels in breastfed infants. Breastfed infants appear not to be adversely affected by maternal or transgender paternal testosterone therapy. High doses of testosterone can suppress lactation. ◉ Effects in Breastfed Infants:After implantation of a 100 mg pellet of testosterone subcutaneously in a postpartum mother, her infant (age not stated) was breastfed (extent not stated). No adverse effects were noted in the infant over a 5-month period. A transgender male began receiving subcutaneous testosterone cypionate 50 mg weekly 13.75 months after giving birth. The dose was increased to 80 mg weekly after 1 month. His male infant was partially “chestfed” (extent not stated) until the infant self-weaned at 137 days after initiation of testosterone (18 months of age). During this time, no adverse events or signs of virilization were noted by the infant’s pediatrician. The infant grew and developed normally. ◉ Effects on Lactation and Breastmilk:Supraphysiologic serum levels of testosterone, either from a tumor or from exogenously administered testosterone, reduces milk production in postpartum women. Testosterone alone reduces serum prolactin; however, when given in combination with estrogen and progestin, serum prolactin levels are not markedly reduced. Testosterone was previously used therapeutically to suppress lactation, usually in combination with an estrogen.

来源:Drugs and Lactation Database (LactMed)

反应信息

• 作为反应物：
  描述：

  睾酮 在 Oxone 、 碳酸氢铵 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以84%的产率得到4,5-Epoxy-testosteron
  参考文献：
  名称：

  Highly Efficient Alkene Epoxidation and Aziridination Catalyzed by Iron(II) Salt + 4,4′,4′′-Trichloro-2,2′:6′,2′′-terpyridine/4,4′′-Dichloro-4′-O-PEG-OCH₃-2,2′:6′,2′′-terpyridine

  摘要：

  **翻译：** “亚铁盐 + 4,4',4"-三氯-2,2':6',2"-三联吡啶”是烯烃环氧化、氮氧化及磺酰胺酯类分子内酰胺化反应的有效催化剂。对环烯烃的环氧化反应表现出优异的非对映异构选择性，最高可达90%。电喷雾电离质谱（ESI-MS）结果支持了亚铁氧和亚铁亚胺中间体的形成。将Cl₃terpy衍生成O-PEG-OCH₃-Cl₂terpy，使三联吡啶结构单元可循环利用，而“亚铁盐 + 4,4'-二氯-4'-O-PEG-OCH₃-2,2':6',2"-三联吡啶”催化体系在烯烃环氧化反应中可重复使用，且催化活性无显著降低。

  DOI：

  10.1021/ol801157m
• 作为产物：
  描述：

  4-androsten-17β-(1,1-dimethylethoxy)-3-one 以86的产率得到睾酮
  参考文献：
  名称：

  Tetrahedron 1991, 47, 6635-6648

  摘要：

  DOI：

文献信息

• Cationic Steroid Antimicrobial Compositions and Methods of Use
  申请人：Savage B. Paul

  公开号：US20070190067A1

  公开（公告）日：2007-08-16

  The invention provides methods for decreasing or inhibiting human immunodeficiency virus (HIV) infection or pathogenesis (e.g., illness) of a cell in vitro, ex vivo or in vivo, a symptom or pathology associated with human immunodeficiency virus (HIV) infection or pathogenesis (e.g., illness) in vitro, ex vivo or in vivo, or an adverse side effect of human immunodeficiency virus (HIV) infection or pathogenesis (e.g., illness) in vitro, ex vivo or in vivo. In one embodiment, a method of the invention includes treating a subject with an invention compound (e.g., cationic steroid antimicrobial or CSA).

  这项发明提供了用于在体外、体外或体内减少或抑制人类免疫缺陷病毒（HIV）感染或病理发生（例如，疾病）、在体外、体外或体内与人类免疫缺陷病毒（HIV）感染或病理发生（例如，疾病）相关的症状或病理、或在体外、体外或体内人类免疫缺陷病毒（HIV）感染或病理发生（例如，疾病）的不良副作用的方法。在一种实施方式中，该发明的方法包括使用一种发明化合物（例如，阳离子类固体抗菌剂或CSA）治疗受试者。
• TESTOSTERONE DERIVATIVES WITH A CARBOXYALKYL SUBSTITUTION IN POSITION 3 AND USE THEREOF FOR THE PRODUCTION OF LABELLED STEROIDS FOR DETERMINING THE CONCENTRATION OF TESTOSTERONE IN A BIOLOGICAL SAMPLE
  申请人：BIOMERIEUX

  公开号：US20150299244A1

  公开（公告）日：2015-10-22

  A testosterone derivative of formula (I): where n is an integer in a range of from 1 to 10, and Y represents an activated or ready-to-be-activated group allowing formation of an amide bond with a primary amine of a molecule. Conjugates including the testosterone derivatives and a marker, methods for determining the concentration of testosterone in a biological sample, and methods for preparing the testosterone derivatives are also provided.

  一种公式为(I)的睾酮衍生物：其中n是1到10范围内的整数，Y代表一个活化或准备激活的基团，允许与分子的初级胺形成酰胺键。还提供了包括睾酮衍生物和标记物的共轭物，用于测定生物样本中睾酮浓度的方法，以及制备睾酮衍生物的方法。
• CATIONIC STEROID ANTIMICROBIAL COMPOSITIONS AND METHODS OF USE
  申请人：SAVAGE PAUL B.

  公开号：US20100330086A1

  公开（公告）日：2010-12-30

  The invention provides methods for decreasing or inhibiting herpesviridae (HV) infection or pathogenesis of a cell in vitro, ex vivo or in vivo, a symptom or pathology associated with a herpesviridae (HV) infection or pathogenesis in vitro, ex vivo or in vivo, or an adverse side effect of herpesviridae (HV) infection or pathogenesis in vitro, ex vivo or in vivo. In one embodiment, a method of the invention includes treating a subject with an invention compound (e.g., cationic steroid antimicrobial or CSA).

  该发明提供了用于在体外、体外或体内减少或抑制细胞感染或发病的疱疹病毒科（HV）的方法，症状或病理与体外、体外或体内疱疹病毒科（HV）感染或发病相关，或在体外、体外或体内疱疹病毒科（HV）感染或发病的不良副作用。在一种实施方式中，该发明的方法包括使用一种发明化合物（例如，阳离子类固醇抗菌药物或CSA）治疗受试者。
• Neocarzinostatin-based hybrid biocatalysts for oxidation reactions
  作者：Elodie Sansiaume-Dagousset、Agathe Urvoas、Kaouthar Chelly、Wadih Ghattas、Jean-Didier Maréchal、Jean-Pierre Mahy、Rémy Ricoux

  DOI：10.1039/c4dt00151f

  日期：——

  has been further associated with a neocarzinostatin variant, NCS-3.24, to generate a new artificial metalloenzyme following the so-called ‘Trojan Horse’ strategy. This new 1-Fe-NCS-3.24 biocatalyst showed an interesting catalytic activity as it was found able to catalyze the chemoselective and slightly enantioselective (ee = 13%) sulfoxidation of thioanisole by H2O2. Molecular modelling studies show that

  阴离子铁（III）-卟啉-睾丸激素共轭物1-Fe已经合成并充分表征。它进一步与新卡斯汀抑制素变体NCS-3.24相关联，以按照所谓的“特洛伊木马”策略生成新的人工金属酶。这种新型的1-Fe -NCS-3.24生物催化剂显示出令人感兴趣的催化活性，因为它能够催化H 2 O 2对硫代苯甲醚的化学选择性和对映选择性（ee = 13％）的硫氧化。分子模型研究表明，类固醇部分与卟啉大环化合物结合到蛋白质结合位点之间的协同作用可以解释实验结果，表明该化合物具有更好的亲和力。NCS-3.24变体的1-Fe含量高于睾丸激素和半胱氨酸半胱氨酸盐本身。他们还表明，Fe-卟啉复合物夹在蛋白质的两个亚结构域之间，具有良好的互补性。但是，人工辅因子完全充满了空腔，其金属离子仍广泛暴露于溶剂中，这说明了观察到的中等对映选择性。提出了“特洛伊木马”策略中的一些可能改进，以获得更好的选择性氧化催化剂。
• [EN] PROCESS FOR THE PREPARATION OF TESTOSTERONE<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE TESTOSTÉRONE
  申请人：ITALIANA SINT SPA

  公开号：WO2011000693A1

  公开（公告）日：2011-01-06

  The present invention relates to an industrial process for the reduction of 4-androstene-3, 17-dione in order to obtain testosterone using a particularly stable and selective enzyme produced in a recombinant manner.

  本发明涉及一种工业过程，用于还原4-雄烯-3,17-二酮以获取睾酮，使用一种特别稳定和选择性的酶，该酶以重组方式产生。

表征谱图