prostaglandin F_2α | 551-11-1

• 物质功能分类: 生物化工 - 生化试剂
• 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 F_2α
• 英文别名: (15S)-9α,11α,15-trihydroxy-prosta-5c,13t-dien-1-oic acid；Prostaglandin F(2α)；Prostaglandin F(2a)；prostaglandin-F_2α；PGF_2α；7-[3,5-Dihydroxy-2-(3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid；(Z)-7-[(1R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
• CAS: 551-11-1；4510-16-1；13164-29-9；23518-25-4；23518-26-5；27415-26-5；28977-22-2；36150-01-3；36150-02-4；37658-84-7；38310-95-1；38432-87-0；39762-37-3；42586-88-9；51262-67-0；51830-20-7；51830-21-8；52521-76-3；54324-23-1；54324-24-2；54324-25-3；54483-31-7；54483-32-8；57759-78-1；57759-79-2；57759-85-0；58717-39-8；59727-54-7；61046-31-9；61302-52-1；62446-65-5；64395-46-6；65026-00-8；65026-01-9；88391-39-3；88391-40-6；99880-86-1；117558-80-2；118456-51-2；123123-44-4；125411-82-7；146388-90-1
• 化学式: C₂₀H₃₄O₅
• 分子量: 354.487
• InChiKey: PXGPLTODNUVGFL-AFSIVQRVSA-N

物化性质

• 沸点：
  531.0±50.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：>100mg/mL； DMSO：>100mg/mL；乙醇：>100mg/mL； PBS pH 7.2：3 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 危险类别：
  1.1A
• 安全说明：
  S28
• 包装等级：
  I
• 危险品运输编号：
  224

制备方法与用途

生物活性

8-Isoprostaglandin F2α 是膜磷脂中花生四烯酸非酶性过氧化产生的异前列腺素。这种化合物以两种形式存在于人血浆中：磷脂酯化和游离酸形式。研究显示，8-Isoprostaglandin F2α 在血管平滑肌中是一种弱的 TP 受体 (TP receptor) 激动剂。

靶点

Human Endogenous Metabolite

反应信息

• 作为产物：
  描述：

  (3aR,5R,6aS)-5-hydroxy-4-[(E)-3-trimethylsilyloxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one 生成 prostaglandin F_2α
  参考文献：
  名称：

  TOLSTIKOV, G. A.;MIFTAXOV, M. S.;ADLER, M. EH.;KOMISSAROVA, N. G., 9 SOV.-IND. SIMP. PO XIMII PRIROD. SOED., RIGA, 15-18 MAYA, 1989, RIGA,(1+

  摘要：

  DOI：

文献信息

• METHOD FOR INTRODUCING SUBSTITUENT INTO alpha,beta-UNSATURATED KETONE AND METHOD FOR SYNTHESIZING PROSTAGLANDIN USING THE SAME
  申请人：NATIONAL CENTER FOR GERIATRICS AND GERONTOLOGY

  公开号：US20210355061A1

  公开（公告）日：2021-11-18

  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.

  本发明提供了一种将取代基引入α，β-不饱和酮的α位和β位的方法，不仅可用于通过三组分偶联过程合成前列腺素，还能够通过一锅法高产率合成前列腺素，而无需使用大量超量的三种合成所需组分之一，也无需使用高毒性重金属作为催化剂或对生物体高毒的溶剂，并提供了一种利用相同技术手段合成前列腺素的方法。 根据本发明，将取代基引入α，β-不饱和酮的方法是一种将取代基引入α，β-不饱和酮的α位和β位碳的方法，包括：第一步，混合烷基锂和三烷基烯基锡，其中锡原子与烯基团的乙烯位结合；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盐化合物。
• POLYMER CONJUGATED PROSTAGLANDIN ANALOGUES
  申请人：O'Shea Michael Shane

  公开号：US20140120058A1

  公开（公告）日：2014-05-01

  The present invention relates in general to polymer-drug conjugates. In particular, the invention relates to polymer-drug conjugates wherein the conjugated drugs are selected from prostaglandins and substituted prostaglandins, to a method of delivering such prostaglandin drugs to a subject, to a sustained drug delivery system comprising the polymer-drug conjugates, to a method of preparing the polymer-drug conjugates, and to an implant comprising the polymer-drug conjugates. The polymer-drug conjugates may be useful for delivering prostaglandins and substituted prostaglandins for the treatment of glaucoma.

  本发明通常涉及聚合物-药物共轭物。具体而言，本发明涉及聚合物-药物共轭物，其中共轭药物选自前列腺素和取代前列腺素，以及将这样的前列腺素药物传递给受体的方法，包括聚合物-药物共轭物的持续性药物传递系统，制备聚合物-药物共轭物的方法，以及包含聚合物-药物共轭物的植入物。聚合物-药物共轭物可用于传递前列腺素和取代前列腺素，用于治疗青光眼。
• Process for the preparation of epoprostenol sodium of enhanced stability
  申请人：CHINOIN GYÓGYSZER ÉS VEGYÉSZETI TERMÉKEK GYÁRA ZRT.

  公开号：US10981884B2

  公开（公告）日：2021-04-20

  The invention provides a stable epoprostenol sodium and a process for the preparation this pharmaceutically active ingredient.

  本发明提供了一种稳定的表前列醇钠和制备这种药物活性成分的工艺。
• Internal 1,15-Lactones Of Fluprostenol And Related Prostaglandin F2a Analogs And Their Use In The Treatment Of Glaucoma And Intraocular Hypertension
  申请人：Maxey Kirk M.

  公开号：US20080146821A1

  公开（公告）日：2008-06-19

  Novel derivatives of prostaglandin compounds of the F-series (PGF), specifically macrocyclic internal 1,15-lactones of fluprostenol and related PGF analogs, such as cloprostenol or latanoprost. The novel analogs can be formulated into ophthalmic solutions and topically applied for the treatment of the increased intraocular pressure caused by glaucoma and the reduction of ocular hypertension.
• COMPOSITIONS AND METHODS FOR TREATING HAIR LOSS USING NON-NATURALLY OCCURRING PROSTAGLANDINS
  申请人：Duke University

  公开号：US20170348214A1

  公开（公告）日：2017-12-07

  A method for treating hair loss in mammals uses compositions containing prostaglandin F analogs. The compositions can be applied topically to the skin. The compositions can arrest hair loss, reverse hair loss, and promote hair growth.