prostaglandin E1 | 745-65-3

• 物质功能分类: 原料药 - 激素及调节内分泌功能类药 - 前列腺素类药
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: prostaglandin E1
• 英文别名: Prostaglandin E₁；(15S)-11α,15-dihydroxy-9-oxo-prost-13t-en-1-oic acid；alprostadil；Prostaglandin E(1)；prostaglandin-E₁；PGE₁；11,15-Dihydroxy-9-oxoprost-13-en-1-oic acid；7-[(1R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid
• CAS: 745-65-3；7004-01-5；20348-58-7；20348-68-9；20348-69-0；20897-91-0；20897-93-2；20897-96-5；20897-98-7；21003-46-3；22468-06-0；23203-65-8；24570-01-2；25140-31-2；38360-96-2；39765-05-4；39765-17-8；39765-18-9；51064-02-9；54324-13-9；54422-21-8；55869-97-1；57759-90-7；57759-91-8；61375-94-8；63229-85-6
• 化学式: C₂₀H₃₄O₅
• 分子量: 354.487
• InChiKey: GMVPRGQOIOIIMI-ZWLIRFKBSA-N

物化性质

• 熔点：
  115-116 °C
• 比旋光度：
  -64 º (c=1.0, C2H5OH)
• 沸点：
  407.69°C (rough estimate)
• 密度：
  1.0458 (rough estimate)
• 溶解度：
  乙醇：1 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  29375000
• 危险品运输编号：
  UN 2811 6.1/PG 3
• 危险类别：
  6.1(b)
• RTECS号：
  GY4569800
• 包装等级：
  III
• 危险性防范说明：
  P264,P270,P301+P310+P330,P405,P501
• 危险性描述：
  H301

制备方法与用途

根据提供的信息,前列腺素E1(PGE1)的主要用途和生产方法包括:

主要用途:

1. 治疗心肌梗塞、心力衰竭、血栓性脉管炎等心血管疾病。
2. 扩张血管,改善微循环。
3. 抑制血小板凝集。
4. 用于引产、催产、肾功能不全等妇产科和泌尿系统疾病。
5. 治疗肝炎、肝硬化、脑梗塞、糖尿病、阳痿等其他疾病。

生产方法:

1. 从羊精囊为原料,经酶制备、有机溶剂提取、硅胶柱分离纯化获得PGE粗品。
2. PGE粗品进一步用硝酸银硅胶柱进行再次纯化,收集PGE1部分。
3. 将PGE1部分浓缩、溶解后加入水洗脱除银离子,再用乙酸乙酯提取得到成品。
4. 近年来也有采用γ-亚麻酸甲酯为起始原料的化学-酶促合成方法,总收率约13%-16%。

该药物的主要药理作用包括扩张血管、抑制血小板聚集等。临床上主要用于治疗多种心血管疾病和妇产科相关疾病。生产工艺经过不断改进,以提高产率和纯度。

文献信息

• AMINO ACID SALTS OF PROSTAGLANDINS
  申请人：DeLong Mitchell A.

  公开号：US20100105775A1

  公开（公告）日：2010-04-29

  The present invention is directed to novel amino acid prostaglandin salts and methods of making and using them.

  本发明涉及新型氨基酸前列腺素盐及其制备和使用方法。
• Method for introducing substituent into α,β-unsaturated ketone and method for synthesizing prostaglandin using the same
  申请人：NATIONAL CENTER FOR GERIATRICS AND GERONTOLOGY

  公开号：US11384044B2

  公开（公告）日：2022-07-12

  The present invention provides a method for introducing substituents into the α-position and the β-position of an α,β-unsaturated ketone, which not only can be used for the synthesis of a prostaglandin by a three-component coupling process, but also enables synthesis of a prostaglandin in a high yield by one-pot operation without requiring the use of a large excess amount of any of the three components required for the synthesis or using a highly toxic heavy metal as a catalyst or a solvent that is highly toxic to living bodies, and a method for synthesizing a prostaglandin using the same technical means. The method for introducing substituents into an α,β-unsaturated ketone according to the present invention is a method for introducing substituents into the carbon at the α-position and the carbon at the β-position of an α,β-unsaturated ketone, including: a first step of mixing alkyllithium and trialkylalkenyl tin in which tin atom binds to the vinyl position of the alkenyl group; a second step of mixing the mixture of the first step and dialkylzinc; a third step of mixing the mixture of the second step and an α,β-unsaturated ketone; and a fourth step of mixing the mixture of the third step and a trifluoromethanesulfonate compound.

  本发明提供了一种在α,β-不饱和酮的α位和β位引入取代基的方法，该方法不仅可用于通过三组分偶联工艺合成前列腺素、而且不需要过量使用合成所需的三种组分中的任何一种，也不需要使用剧毒重金属作为催化剂或对生物体有剧毒的溶剂，就能通过一锅操作高产率地合成前列腺素，以及使用相同技术手段合成前列腺素的方法。 根据本发明的向α，β-不饱和酮中引入取代基的方法是一种向α，β-不饱和酮的α位碳和β位碳中引入取代基的方法，包括：第一步，混合烷基锂和三烷基烯基锡，其中锡原子与烯基的乙烯基位置结合；第二步，混合第一步的混合物和二烷基锌；第三步，混合第二步的混合物和α，β-不饱和酮；第四步，混合第三步的混合物和三氟甲磺酸化合物。
• EMULSION COMPOSITION COMPRISING PROSTAGLANDIN E1
  申请人：LIN Yi-Fong

  公开号：US20080234376A1

  公开（公告）日：2008-09-25

  An emulsion composition includes prostaglandin E 1 (PGE 1 ), a phospholipid with a high purity and a non-proton-providing surfactant that improves stability of PGE 1 . Embodiments of the emulsion composition include an effective amount of PGE 1 , about 1% to about 30% (w/w) of a pharmaceutically acceptable oil as an oil base based on the weight of the emulsion composition, about 1% to about 30% (w/w) of a phospholipid with a high purity based on the weight of the oil base, about 1.6% to about 40% (w/w) of a non-proton-providing surfactant based on the weight of the oil base, and the balance of the emulsion composition being water.
• COMPOSITIONS FOR PROLIFERATION OF CELLS AND RELATED METHODS
  申请人：Miller Freda

  公开号：US20110301105A1

  公开（公告）日：2011-12-08

  We have discovered that p63 inhibition results in increased cellular proliferation. We have also performed a screen for agents capable of increasing cellular proliferation, (e.g., of stem cells such as skin-derived precursors (SKPs)). The invention therefore invention provides compositions, methods, and kits for increasing proliferation of cells, using compounds that decrease p63 expression or activity or using the compounds described herein. The invention also features methods of using these compounds for increasing hair growth, improving skin health, or promoting skin repair in a subject.
• US8748177B2
  申请人：——

  公开号：US8748177B2

  公开（公告）日：2014-06-10