N-palmitoylethanolamine-o-(succinyl(triethylene glycol)) | 1613511-75-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-palmitoylethanolamine-o-(succinyl(triethylene glycol))
• 英文别名: triethylene glycol 2-palmitamidoethyl succinate；1-O-[2-(hexadecanoylamino)ethyl] 4-O-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl] butanedioate
• CAS: 1613511-75-3
• 化学式: C₂₈H₅₃NO₈
• 分子量: 531.731
• InChiKey: ADOVRKXBKSUINV-UHFFFAOYSA-N

物化性质

• 沸点：
  654.0±50.0 °C(Predicted)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  37
• 可旋转键数：
  30
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  十六酰胺乙醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 N-palmitoylethanolamine-o-(succinyl(triethylene glycol))
  参考文献：
  名称：

  POLYETHYLENE GLYCOL DERIVATIVES OF PALMITOYLETHANOLAMIDE AND ANALOGOUS ACYLETHANOLAMIDES

  摘要：

  一系列聚乙二醇酯和碳酸酯的PEA及其类似的酰乙醇胺共轭物具有更高的水溶性和良好的亲水/疏水平衡，导致（i）在组织中（特别是皮肤和粘膜）的积累增加，（ii）释放延长，以及（iii）生物利用度增加。PEA和类似的酰乙醇胺在组织中（特别是皮肤和粘膜）的水平提高以及它们的延长释放是由于相关共轭物生物利用度的提高。共轭物能够延长PEA和类似的酰乙醇胺发挥药理效应的时间范围。

  公开号：

  US20150157733A1

文献信息

• Polyethylene glycol derivatives of palmitoylethanolamide and analogous acylethanolamides
  申请人：EPITECH GROUP S.p.A.

  公开号：EP2742957B1

  公开（公告）日：2018-03-21
• Improvement of Topical Palmitoylethanolamide Anti-Inflammatory Activity by Pegylated Prodrugs
  作者：Diana Tronino、Roberto Russo、Carmine Ostacolo、Angelica Mazzolari、Carmen De Caro、Carmen Avagliano、Sonia Laneri、Giovanna La Rana、Antonia Sacchi、Francesco Della Valle、Giulio Vistoli、Antonio Calignano

  DOI：10.1021/acs.molpharmaceut.5b00397

  日期：2015.9.8

  A small library of polyethylene glycol esters of palmitoylethanolamide (PEA) was synthesized with the aim of improving the pharmacokinetic profile of the parent drug after topical administration. Synthesized prodrugs were studied for their skin accumulation, pharmacological activities, in vitro chemical stability, and in silico enzymatic hydrolysis. Prodrugs proved to be able to delay and prolong the pharmacological activity of PEA by modification of its skin accumulation profile. Pharmacokinetic improvements were particularly evident when specific structural requirements, such as flexibility and reduced molecular weight, were respected. Some of the synthesized prodrugs prolonged the pharmacological effects 5 days following topical administration, while a formulation composed by PEA and two pegylated prodrugs showed both rapid onset and long-lasting activity, suggesting the potential use of polyethylene glycol pro drugs of PEA as a suitable candidate for the treatment of skin inflammatory diseases.