17Alpha-羟基黄体酮 | 68-96-2

• 物质功能分类: 原料药 - 激素及调节内分泌功能类药 - 避孕药
• 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
• 中文名称: 17Alpha-羟基黄体酮
• 中文别名: 羟孕酮；羟黄酮；17α-羟孕酮；17a-羟基黄体酮；17α-羟基孕甾-4-烯-3,20-二酮；17Alpha-羟基孕酮；17Alpha-羟孕酮；17Α-羟基孕甾酮；17-alpah-羟基黄体酮；17α-羟基孕酮；17-ALPHA-羟基孕酮；17a-羟基-黄体酮；17α-羟基黄体酮
• 英文名称: 17-hydroxyprogesterone
• 英文别名: 17α hydroxyprogesterone；17alpha-hydroxyprogesterone；hydroxyprogesterone；(8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 68-96-2
• 化学式: C₂₁H₃₀O₃
• mdl: MFCD00003659
• 分子量: 330.467
• InChiKey: DBPWSSGDRRHUNT-CEGNMAFCSA-N

物化性质

• 熔点：
  276°C
• 沸点：
  407.89°C (rough estimate)
• 密度：
  1.0998 (rough estimate)
• 闪点：
  9℃
• 溶解度：
  溶于氯仿
• 物理描述：
  Solid
• 颜色/状态：
  RHOMBIC OR HEXAGONAL LEAFLETS FROM ACETONE OR ALCOHOL
• 稳定性/保质期：

  CRYSTALS SHOULD NOT BE EXPOSED TO HEAT & LIGHT /CAPROATE/

• 旋光度：
  SPECIFIC OPTICAL ROTATION (CHLOROFORM, 1.0417%): +105.6 DEG @ 17 °C/D
• 碰撞截面：
  183.4 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]
• 保留指数：
  2991.9

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.809
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

17alpha-羟基孕酮的人体代谢物包括17Beta-21-二羟基孕酮。

17alpha-hydroxy-progesterone has known human metabolites that include 17Beta-21-dihydroxyprogesterone.

来源:NORMAN Suspect List Exchange

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 相互作用

...雌激素增强了黄体酮的抑制效果，导致了两种混合使用的普遍采用。/黄体酮/

...ESTROGEN ENHANCED SUPPRESSIVE EFFECT OF PROGESTIN & LED TO GENERAL USE OF MIXTURE OF TWO. /PROGESTINS/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

可能导致注射部位出现水肿和局部反应。

...MAY CAUSE EDEMA & LOCAL REACTIONS @ SITE OF INJECTION.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

最常见的副作用是恶心、水肿和不规则阴道出血。其他报告的副作用包括体重增加、性欲降低、抑郁、黄疸和充血性心力衰竭。/醋酸孕酮/

MOST COMMON EFFECTS ARE NAUSEA, EDEMA, & IRREGULAR VAGINAL BLEEDING. OTHER REPORTED EFFECTS INCL WT GAIN, DECR LIBIDO, DEPRESSION, JAUNDICE, & CONGESTIVE HEART FAILURE. /CAPROATE/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

...己酸羟孕酮偶尔会导致过敏反应、咳嗽或呼吸困难。在罕见情况下，它可能会导致女胎儿男性化。/己酸酯/

...HYDROXYPROGESTERONE CAPROATE OCCASIONALLY CAUSES HYPERSENSITIVITY, COUGHING, OR DYSPNEA. IN RARE INSTANCES IT MAY CAUSE VIRILIZATION OF FEMALE FETUS. /CAPROATE/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

作用持续时间比孕酮长，但其起效较慢。油溶液中的羟孕酮己酸酯单次注射将产生1-2周的孕激素效应。

...DURATION OF ACTION IS LONGER /THAN PROGESTERONE/, BUT ITS ONSET OF ACTION IS SLOWER. SINGLE INJECTION OF SOLN OF HYDROXYPROGESTERONE CAPROATE IN OIL WILL EXERT PROGESTATIONAL EFFECTS FOR 1-2 WK. /CAPROATE/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

大约50-60%的放射性黄体酮出现在尿液中，大约10%出现在粪便中。当黄体酮在周期的黄体期或怀孕期间长时间给予时，较大比例（25-30%）的黄体酮以 pregnanediol 的形式出现在尿液中。/黄体酮/

ABOUT 50-60% OF ADMIN RADIOACTIVE PROGESTERONE APPEARS IN URINE & ABOUT 10% IN FECES. ... WHEN PROGESTERONE IS GIVEN FOR PROLONGED PERIOD, DURING LUTEAL PHASE OF CYCLE, OR DURING PREGNANCY, LARGER PROPORTION (25-30%) APPEARS IN URINE AS PREGUANEDIOL. /PROGESTERONE/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

内源性黄体酮的转化率异常迅速，血液中的半衰期仅为几分钟，毫无疑问，外源性物质的处理方式也是如此。少量的黄体酮储存在体内脂肪中...推测，从肠道吸收是迅速的，但在通过肝脏的过程中，该化合物会迅速转化.../黄体酮/

RATE OF TURNOVER OF ENDOGENOUS PROGESTERONE IS UNUSUALLY RAPID, T/2 IN BLOOD BEING FEW MIN, & DOUBTLESS EXOGENOUS MATERIAL IS HANDLED IN SAME WAY. SMALL AMT...IS STORED IN BODY FAT... PRESUMABLY, ABSORPTION FROM INTESTINAL TRACT IS PROMPT, BUT COMPD IS RAPIDLY TRANSFORMED DURING PASSAGE THROUGH LIVER... /PROGESTERONE/

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  T
• 安全说明：
  S22,S36/37/39,S45,S53
• 危险类别码：
  R61
• WGK Germany：
  3
• 海关编码：
  38220090
• 危险品运输编号：
  UN1230 - class 3 - PG 2 - Methanol, solution
• RTECS号：
  TU5060000

制备方法与用途

简介

17α-羟孕酮，有时简称为羟孕酮（英语：hydroxyprogesterone，OHP），是一种类似于孕酮的内源性孕激素类甾体激素，也是许多内源性甾体激素生物合成的前体，包括雄激素、雌激素、糖皮质激素和盐皮质激素以及一些神经甾体。

生物活性

17-羟孕酮（17-OHP）是一种内源性孕激素，在类固醇激素如雄性激素、雌性激素、糖皮质激素、盐皮质激素的生物合成过程中扮演着化学中间体的角色。

体外研究

17α-羟孕酮是一种类似于孕酮的孕激素受体激动剂，虽然效果较弱。它还参与了类固醇激素如雄性激素和雌性激素的生物合成过程中的化学反应。

体内研究

17-羟孕酮是一个有效的生殖泡破裂（GVBD）诱导剂。

化学性质

17α-羟孕酮为白色结晶，熔点221℃（219-220℃），在氯仿中测量的比旋度为[α]20/D+97°。

用途

17α-羟孕酮用作氢化可的松、甲地孕酮、己酸孕酮等甾体激素药物中间体，也可作为长效孕激素使用。

生产方法

可通过从薯蓣皂素出发，经过开环、乙酰化、氧化、水解、环氧化、氧化、加成和催化氢化等一系列反应制备得到。

反应信息

• 作为反应物：
  描述：

  17Alpha-羟基黄体酮 在 二氧化碳 、 adenomatous and surrounding adrenal tissue of patients with Cushing's syndrome 、 Krebs-Ringer bicarbonate solution 、 primary aldosteronism or renal cell carcinoma 、 氧气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 氢化可的松
  参考文献：
  名称：

  Differences between adrenal adenoma causing primary aldosteronism and other adrenal tissues in the incorporation of labeled steroid precursors into their products

  摘要：

  The incorporation and conversion of several labeled steroid precursors into their products were examined in slices of adrenal tissue from two patients with primary aldosteronism and compared with that in "normal" adrenal tissue and adrenal tissues from a patient with Cushing's syndrome. The products of the incorporation were separated by Sephadex LH-20 column chromatography. The major products of conversion in the adenomatous tissue of primary aldosteronism were 18-hydroxycorticosterone and lesser amounts of aldosterone. Smaller amounts of 18-hydroxycorticosterone were isolated from all other adrenal tissues studied. No aldosterone could be recovered after incubating any of the adrenal tissue studied with labeled 18-hydroxy-11-deoxycorticosterone or 18-hydroxycorticosterone as precursor steroid. These in vitro results seem to suggest that there is increased 18-hydroxylation in the adenoma of primary aldosteronism compared with other tissues and that relatively more 18-hydroxycorticosterone is produced in such tissue than aldosterone.

  DOI：

  10.1016/0039-128x(80)90076-8
• 作为产物：
  描述：

  progesterone 在 sporormia minima 作用下， 生成 17Alpha-羟基黄体酮
  参考文献：
  名称：

  17alpha oxygenation of steroids by sporormia

  摘要：

  公开号：

  US02813060A1

文献信息

• IRAK DEGRADERS AND USES THEREOF
  申请人：Kymera Therapeutics, Inc.

  公开号：US20190192668A1

  公开（公告）日：2019-06-27

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用这些化合物的方法。
• [EN] PYRAZOLOPYRIMIDINES AS CYCLIN DEPENDENT KINASE INHIBITORS<br/>[FR] PYRAZOLOPYRIMIDINES UTILES EN TANT QU'INHIBITEURS DE KINASES DEPENDANTES DES CYCLINES
  申请人：SCHERING CORP

  公开号：WO2004022062A1

  公开（公告）日：2004-03-18

  In its many embodiments, the present invention provides a novel class of pyrazolo[1,5-a]pyrimidine compounds as inhibitors of cyclin dependent kinases, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the CDKs using such compounds or pharmaceutical compositions.

  在其多种实施方式中，本发明提供了一类新型的吡唑并[1,5-a]嘧啶化合物，作为细胞周期依赖性激酶的抑制剂，以及制备这类化合物的方法，含有一种或多种这类化合物的药物组合物，制备包含一种或多种这类化合物的药物配方的方法，以及利用这类化合物或药物组合物治疗、预防、抑制或改善与CDKs相关的一种或多种疾病的方法。
• [EN] PYRAZOLOPYRIMIDINES AS CYCLIN-DEPENDENT KINASE INHIBITORS<br/>[FR] PYRAZOLOPYRIMIDINES TENANT LIEU D'INHIBITEURS DE KINASES DEPENDANTES DE LA CYCLINE
  申请人：SCHERING CORP

  公开号：WO2004022561A1

  公开（公告）日：2004-03-18

  In its many embodiments, the present invention provides a novel class of pyrazolo[1,5-a]pyrimidine compounds as inhibitors of cyclin dependent kinases, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the CDKs using such compounds or pharmaceutical compositions.

  在其多种实施方式中，本发明提供了一类新型的吡唑并[1,5-a]嘧啶化合物，作为细胞周期依赖性激酶的抑制剂，以及制备这类化合物的方法，含有一种或多种这类化合物的药物组合物，制备包含一种或多种这类化合物的药物配方的方法，以及利用这类化合物或药物组合物治疗、预防、抑制或改善与CDKs相关的一种或多种疾病的方法。
• [EN] IMIDAZOLIUM REAGENT FOR MASS SPECTROMETRY<br/>[FR] RÉACTIF D'IMIDAZOLIUM POUR SPECTROMÉTRIE DE MASSE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2021234004A1

  公开（公告）日：2021-11-25

  The present invention relates to compounds which are suitable to be used in mass spectrometry as well as methods of mass spectrometric determination of analyte molecules using said compounds.

  本发明涉及适用于质谱的化合物，以及利用该化合物进行分析物分子的质谱测定方法。
• Heterocyclic Compounds as MEK Inhibitors
  申请人：Chikkanna Dinesh

  公开号：US20090275606A1

  公开（公告）日：2009-11-05

  The present invention relates to compounds of formula I and pharmaceutically acceptable salts. These compounds can act as potential MEK inhibitors in the treatment of hyperproliferative diseases, like cancer and inflammation. The present invention also reveals methods of preparation thereof.

  本发明涉及公式I的化合物和药用盐。这些化合物可以作为潜在的MEK抑制剂，用于治疗癌症和炎症等过度增殖性疾病。本发明还揭示了其制备方法。