丙米嗪N-beta-D-葡糖苷酸 | 165602-94-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 中文名称: 丙米嗪N-beta-D-葡糖苷酸
• 英文名称: Imipramine N-glucuronide
• 英文别名: imipramine N-β-D-glucuronide；imipramine-N-glucuronide；(2S,3S,4S,5R,6R)-6-[3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl-dimethylazaniumyl]-3,4,5-trihydroxyoxane-2-carboxylate
• CAS: 165602-94-8
• 化学式: C₂₅H₃₂N₂O₆
• 分子量: 456.539
• InChiKey: CXPKQHSXFUNBMP-OSFFKXSWSA-N

物化性质

• 熔点：
  >123oC (dec.)
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  丙米嗪N-beta-D-葡糖苷酸 在 盐酸 作用下， 以 水 为溶剂， 生成 米帕明
  参考文献：
  名称：

  人体中三种新的安非他酮代谢物的鉴定和结构表征

  摘要：

  安非他酮是一种广泛使用的抗抑郁药和推荐的CYP2B6探针药物。但是，目前对安非他酮消除途径的理解是有限的。安非他酮具有三种活性循环代谢物，OH-安非他酮，苏氢安非他酮和赤氢安非他酮，但与这些安非他酮一起，这些代谢物及其在尿液中的结合物仅占剂量的23％，并且大多数安非他酮消除途径导致未表征的代谢物。这项研究的目的是使用人类临床样品和体外孵育来确定未表征的安非他酮代谢物的结构。在人肝微粒体温育中检测到三种新的代谢物4'-OH-安非他酮，赤型4'-OH-氢安非他酮和threo-4'-OH-氢安非他酮，并从人尿液中分离出来。通过将紫外线吸收率，NMR光谱和质谱数据与合成标准样品进行比较，确认了代谢物的结构。这些代谢物合计占尿中排泄的药物相关物质的24％。

  DOI：

  10.1021/acsmedchemlett.6b00189
• 作为产物：
  描述：

  3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl-[(2R,3R,4S,5S,6S)-6-methoxycarbonyl-3,4,5-tris(2-methylpropanoyloxy)oxan-2-yl]-dimethylazanium;trifluoromethanesulfonate 在 水 、 lithium hydroxide 作用下， 以 甲醇 为溶剂， 以0.064 g的产率得到丙米嗪N-beta-D-葡糖苷酸
  参考文献：
  名称：

  A convenient new synthesis of quaternary ammonium glucuronides of drug molecules

  摘要：

  N-Glucuronides, of various Structural types, are frequently encountered as drug metabolites. Efficient chemical synthesis of these compounds, both as analytical standards and for toxicological investigation, is therefore an important goal. Earlier syntheses of N+-glucuronides of aliphatic tertiary amine drugs involved direct reaction of the drug molecule with a bromosugar, but yields were generally low and of poor reproducibility, with many by-products. In addition the final products were often of low stability, hindering effective isolation and purification. We now report that a stable, readily prepared glucuronic acid hemiacetal is a reliable precursor for metabolites of this type and give three pharmaceutically relevant examples. We report further on the stability of the final metabolites and the conditions required for their isolation and purification. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.113

文献信息

• A convenient new synthesis of quaternary ammonium glucuronides of drug molecules
  作者：Lisa Iddon、Ryan A. Bragg、John R. Harding、Andrew V. Stachulski

  DOI：10.1016/j.tet.2009.10.113

  日期：2010.1

  N-Glucuronides, of various Structural types, are frequently encountered as drug metabolites. Efficient chemical synthesis of these compounds, both as analytical standards and for toxicological investigation, is therefore an important goal. Earlier syntheses of N+-glucuronides of aliphatic tertiary amine drugs involved direct reaction of the drug molecule with a bromosugar, but yields were generally low and of poor reproducibility, with many by-products. In addition the final products were often of low stability, hindering effective isolation and purification. We now report that a stable, readily prepared glucuronic acid hemiacetal is a reliable precursor for metabolites of this type and give three pharmaceutically relevant examples. We report further on the stability of the final metabolites and the conditions required for their isolation and purification. (C) 2009 Elsevier Ltd. All rights reserved.
• Identification and Structural Characterization of Three New Metabolites of Bupropion in Humans
  作者：Jennifer E. Sager、John R. Choiniere、Justine Chang、Alyssa Stephenson-Famy、Wendel L. Nelson、Nina Isoherranen

  DOI：10.1021/acsmedchemlett.6b00189

  日期：2016.8.11

  incubations. Three new metabolites, 4′-OH-bupropion, erythro-4′-OH-hydrobupropion, and threo-4′-OH-hydrobupropion, were detected in human liver microsome incubations and were isolated from human urine. The structures of the metabolites were confirmed via comparison of UV absorbance, NMR spectra, and mass spectral data to those of the synthesized standards. In total, these metabolites represented 24% of

  安非他酮是一种广泛使用的抗抑郁药和推荐的CYP2B6探针药物。但是，目前对安非他酮消除途径的理解是有限的。安非他酮具有三种活性循环代谢物，OH-安非他酮，苏氢安非他酮和赤氢安非他酮，但与这些安非他酮一起，这些代谢物及其在尿液中的结合物仅占剂量的23％，并且大多数安非他酮消除途径导致未表征的代谢物。这项研究的目的是使用人类临床样品和体外孵育来确定未表征的安非他酮代谢物的结构。在人肝微粒体温育中检测到三种新的代谢物4'-OH-安非他酮，赤型4'-OH-氢安非他酮和threo-4'-OH-氢安非他酮，并从人尿液中分离出来。通过将紫外线吸收率，NMR光谱和质谱数据与合成标准样品进行比较，确认了代谢物的结构。这些代谢物合计占尿中排泄的药物相关物质的24％。