iodomethyl heptanoate | 199671-26-6

• 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: iodomethyl heptanoate
• CAS: 199671-26-6
• 化学式: C₈H₁₅IO₂
• 分子量: 270.11
• InChiKey: AHWAPPBPAIVQBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  iodomethyl heptanoate 在 potassium acetate 、 silver nitrate 作用下， 以 水 为溶剂， 生成 Potassium; (5E,9E)-1-(bis-heptanoyloxymethoxy-phosphoryl)-6,10,14-trimethyl-pentadeca-5,9,13-triene-1-sulfonate
  参考文献：
  名称：

  口服角鲨烯合酶抑制剂：α-膦磺酸基部分的双（（酰氧基）烷基）前药。

  摘要：

  DOI：

  10.1021/jm950735s
• 作为产物：
  描述：

  庚酸氯甲酯 在 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 90.0h， 生成 iodomethyl heptanoate
  参考文献：
  名称：

  Creation of a long-acting rilpivirine prodrug nanoformulation

  摘要：

  Antiretroviral therapy requires lifelong daily dosing to attain viral suppression, restore immune function, and improve quality of life. As a treatment alternative, long-acting (LA) antiretrovirals can sustain therapeutic drug concentrations in blood for prolonged time periods. The success of recent clinical trials for LA parenteral cabotegravir and rilpivirine highlight the emergence of these new therapeutic options. Further optimization can improve dosing frequency, lower injection volumes, and facilitate drug-tissue distributions. To this end, we report the synthesis of a library of RPV prodrugs designed to sustain drug plasma concentrations and improved tissue biodistribution. The lead prodrug M3RPV was nanoformulated into the stable LA injectable NM3RPV. NM3RPV treatment led to RPV plasma concentrations above the protein-adjusted 90% inhibitory concentration for 25 weeks with substantial tissue depots after a single intramuscular injection in BALB/cJ mice. NM3RPV elicited 13- and 26-fold increases in the RPV apparent half-life and mean residence time compared to native drug formulation. Taken together, proof-of-concept is provided that nanoformulated RPV prodrugs can extend the apparent drug half-life and improve tissue biodistribution. These results warrant further development for human use.

  DOI：

  10.1016/j.jconrel.2019.09.001

文献信息

• [EN] ANTIVIRAL PRODRUGS AND FORMULATIONS THEREOF<br/>[FR] PROMÉDICAMENTS ANTIVIRAUX ET FORMULATIONS DE CEUX-CI
  申请人：UNIV NEBRASKA

  公开号：WO2019199756A1

  公开（公告）日：2019-10-17

  The present invention provides prodrugs and methods of use thereof.

  本发明提供了前药及其使用方法。
• Prodrugs of CL316243: a selective β3-adrenergic receptor agonist for treating obesity and diabetes
  作者：F.W. Sum、A. Gilbert、A.M. Venkatesan、K. Lim、V. Wong、M. O'Dell、G. Francisco、Z. Chen、G. Grosu、J. Baker、J. Ellingboe、M. Malamas、I. Gunawan、J. Primeau、E. Largis、K. Steiner

  DOI：10.1016/s0960-894x(99)00316-9

  日期：1999.7

  CL316243 is a highly selective and potent beta(3)-adrenergic receptor agonist, and has been shown in rodent models to be an effective agent for treating obesity and Type II diabetes. To improve the oral absorption and pharmacokinetic profiles of CL316243, a number of prodrugs have been synthesized and evaluated. Several ester-type prodrugs show significant improvements in oral bioavailability in both rodent and primate models, (C) 1999 Elsevier Science Ltd. All rights reserved.