(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione;nonanedioic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione;nonanedioic acid
• 化学式: C₉H₁₆O₄*C₃₇H₆₇NO₁₃
• 分子量: 922.162
• InChiKey: UJLMLRHYEXBHIE-YZPBMOCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  64
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  269
• 氢给体数：
  7
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  disodium azelainate 、 红霉素 在 phosphate buffer 作用下， 生成 (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione;nonanedioic acid
  参考文献：
  名称：

  Optimization of Topical Erythromycin Formulations by Ion Pairing

  摘要：

  红霉素（ERY）用于治疗痤疮。为了显著减少微生物的数量，抗生素必须渗透到皮脂腺囊中。首先，本研究旨在通过离子对形成提高ERY的亲脂性。其次，开发了一种具有优化离子对渗透的配方。第三，将优化的配方与含有乙醇的配方以及商业产品Zine-ryt®进行比较。脂溶性的测定基于分配系数（PC）和ERY进入修饰的多层膜系统（MMS）的渗透。结果显示，当ERY与十八烷磺酸盐之间形成离子对时，其进入亲脂性受体系统的渗透性比单独使用ERY基体时高出三倍。通过为离子对优化载体，可以显著减少抗生素的用量。

  DOI：

  10.1159/000211363

文献信息

• Optimization of Topical Erythromycin Formulations by Ion Pairing
  作者：S. Matschiner、R. Neubert、W. Wohlrab

  DOI：10.1159/000211363

  日期：——

  Erythromycin (ERY) is used in the topical treatment of acne vulgaris. In order to decrease the amount of microorganisms markedly, the antibiotic must penetrate into the sebaceous follicles. Firstly, the aim of this study was to improve the lipo-philicity of ERY by ion pairing. Secondly, a formulation with optimized penetration of the ion pair was developed. Thirdly, the optimized formulation was compared with formulations containing ethanol and with the commercial product Zine-ryt®. The determination of lipophilicity was based on partition coefficients (PC) and on the penetration of ERY into a modified multilayer membrane system (MMS). It was shwon that the penetration of ERY into a lipophilic acceptor system was three times higher when ion pairing between ERY and octadecansulfonate was used in comparison with the penetration of the ERY base alone. The dosage of the antibiotic used can be markedly reduced by optimizing a vehicle for the ion pair.

  红霉素（ERY）用于治疗痤疮。为了显著减少微生物的数量，抗生素必须渗透到皮脂腺囊中。首先，本研究旨在通过离子对形成提高ERY的亲脂性。其次，开发了一种具有优化离子对渗透的配方。第三，将优化的配方与含有乙醇的配方以及商业产品Zine-ryt®进行比较。脂溶性的测定基于分配系数（PC）和ERY进入修饰的多层膜系统（MMS）的渗透。结果显示，当ERY与十八烷磺酸盐之间形成离子对时，其进入亲脂性受体系统的渗透性比单独使用ERY基体时高出三倍。通过为离子对优化载体，可以显著减少抗生素的用量。