O-butyryloxprenolol | 144106-11-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: O-butyryloxprenolol
• 英文别名: [1-(Propan-2-ylamino)-3-(2-prop-2-enoxyphenoxy)propan-2-yl] butanoate
• CAS: 144106-11-6
• 化学式: C₁₉H₂₉NO₄
• 分子量: 335.444
• InChiKey: RHWZRIPDTCOSGR-UHFFFAOYSA-N

物化性质

• 沸点：
  439.7±45.0 °C(Predicted)
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O-butyryloxprenolol 在 borate buffer 作用下， 以 甲醇 、 水 为溶剂， 生成 丁酸 、 氧烯洛尔
  参考文献：
  名称：

  A Study of the Relationship between the Structure and Physicochemical Parameters of a Homologous Series of Oxprenolol Esters at Various pH Values and Temperatures

  摘要：

  A number of beta-adrenergic blockers, including timolol and propranolol, are administered in eyedrops for the treatment of glaucoma, but their therapeutic value is limited by a relatively high incidence of cardiovascular and respiratory side effects. Because of poor ocular bioavailability, many ocular drugs are applied in high concentrations, which give rise to both ocular and systemic side effects. Methods to increase ocular bioavailability include (a) the development of drug delivery devices designed to release drugs at controlled rates, (b) the use of various vehicles that retard precorneal drug loss, and (c) the conversion of drugs to biologically reversible derivatives (prodrugs) with increased corneal penetration properties, from which the active drugs are released by enzymatic hydrolysis. A homologous series of aliphatic esters of oxprenolol were synthesized and investigated as potential prodrugs for ocular use. The stability of each O-acyl derivative was investigated in aqueous solutions over the pH range 2.2-9.0 at 37 degrees C. The observed rate constants (k(obs)), shelf-lives (t(90)), lipophilicities, and Arrhenius parameters were determined for each ester. A study of the relationship between the structure and physicochemical parameters of the homologous series of oxprenolol esters at various pH values and temperatures was made.

  DOI：

  10.1021/js970112x
• 作为产物：
  描述：

  盐酸氧烯洛尔 、 丁酰氯 生成 O-butyryloxprenolol
  参考文献：
  名称：

  在生物酶存在下，酯部分碳链长度的增加如何影响一系列同源的氧丁诺尔酯的稳定性

  摘要：

  β-受体阻滞剂（包括噻吗洛尔和普萘洛尔）以滴眼剂的形式给药，用于治疗青光眼。由于心血管和呼吸道副作用的发生率很高，因此其治疗价值受到限制。由于不良的眼生物利用度，许多眼药以高浓度应用，这引起了眼和全身的副作用。因此，已经采用了一些方法来增加眼部生物利用度，例如（a）开发设计成以可控速率释放药物的药物递送装置，（b）使用各种阻碍角膜前药物损失的媒介物，以及（c）转化将药物转化为具有增加的角膜渗透特性的生物可逆衍生物（前药），通过酶促水解从中释放活性药物。合成了一系列与结构相关的氧丁诺醇酯，并将其作为改善眼部使用的潜在前药进行了研究。在磷酸盐缓冲液（pH 7.4）中，以及在（a）30％的人血浆，（b）房水和（c）在pH 7. 4和37℃下的角膜提取物的存在下，研究了每种酯的稳定性。给出了在生物酶存在下同源系列的氧丁诺醇酯的稳定性如何受到酯部分的碳链长度增加的影响。

  DOI：

  10.1021/js970280p

文献信息

• Nogowska, Acta poloniae pharmaceutica, 2000, vol. 57, # 5, p. 353 - 357
  作者：Nogowska

  DOI：——

  日期：——
• A Study of the Relationship between the Structure and Physicochemical Parameters of a Homologous Series of Oxprenolol Esters at Various pH Values and Temperatures
  作者：C. Geraldine M. Jordan

  DOI：10.1021/js970112x

  日期：1997.10

  A number of beta-adrenergic blockers, including timolol and propranolol, are administered in eyedrops for the treatment of glaucoma, but their therapeutic value is limited by a relatively high incidence of cardiovascular and respiratory side effects. Because of poor ocular bioavailability, many ocular drugs are applied in high concentrations, which give rise to both ocular and systemic side effects. Methods to increase ocular bioavailability include (a) the development of drug delivery devices designed to release drugs at controlled rates, (b) the use of various vehicles that retard precorneal drug loss, and (c) the conversion of drugs to biologically reversible derivatives (prodrugs) with increased corneal penetration properties, from which the active drugs are released by enzymatic hydrolysis. A homologous series of aliphatic esters of oxprenolol were synthesized and investigated as potential prodrugs for ocular use. The stability of each O-acyl derivative was investigated in aqueous solutions over the pH range 2.2-9.0 at 37 degrees C. The observed rate constants (k(obs)), shelf-lives (t(90)), lipophilicities, and Arrhenius parameters were determined for each ester. A study of the relationship between the structure and physicochemical parameters of the homologous series of oxprenolol esters at various pH values and temperatures was made.
• How an Increase in the Carbon Chain Length of the Ester Moiety Affects the Stability of a Homologous Series of Oxprenolol Esters in the Presence of Biological Enzymes
  作者：C. Geraldine M. Jordan

  DOI：10.1021/js970280p

  日期：1998.7

  hydrolysis. A series of structurally related oxprenolol esters were synthesized and investigated as potential prodrugs for improved ocular use. The stability of each ester was studied in phosphate buffer (pH 7.4), also in the presence of (a) 30% human plasma, (b) aqueous humor, and (c) corneal extract at pH 7. 4 and at 37 degreesC. An account is given of how the stability of a homologous series of oxprenolol

  β-受体阻滞剂（包括噻吗洛尔和普萘洛尔）以滴眼剂的形式给药，用于治疗青光眼。由于心血管和呼吸道副作用的发生率很高，因此其治疗价值受到限制。由于不良的眼生物利用度，许多眼药以高浓度应用，这引起了眼和全身的副作用。因此，已经采用了一些方法来增加眼部生物利用度，例如（a）开发设计成以可控速率释放药物的药物递送装置，（b）使用各种阻碍角膜前药物损失的媒介物，以及（c）转化将药物转化为具有增加的角膜渗透特性的生物可逆衍生物（前药），通过酶促水解从中释放活性药物。合成了一系列与结构相关的氧丁诺醇酯，并将其作为改善眼部使用的潜在前药进行了研究。在磷酸盐缓冲液（pH 7.4）中，以及在（a）30％的人血浆，（b）房水和（c）在pH 7. 4和37℃下的角膜提取物的存在下，研究了每种酯的稳定性。给出了在生物酶存在下同源系列的氧丁诺醇酯的稳定性如何受到酯部分的碳链长度增加的影响。