托美丁葡糖苷酸 | 71595-19-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 托美丁葡糖苷酸
• 中文别名: 5-甲氧基鬼臼毒
• 英文名称: Tolmetin 1-β-O-glucuronide
• 英文别名: tolmetin β-D-glucuronide；Tolmetin glucuronide；(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetyl]oxyoxane-2-carboxylic acid
• CAS: 71595-19-2
• 化学式: C₂₁H₂₃NO₉
• 分子量: 433.415
• InChiKey: MEFIGCPEYJZFFC-ZFORQUDYSA-N

物化性质

• 熔点：
  139-142°C
• 沸点：
  706.1±60.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微）、甲醇（轻微、加热）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  156
• 氢给体数：
  4
• 氢受体数：
  9

ADMET

代谢

Tolmetin glucuronide 是 Tolmetin 的人体已知代谢物。

Tolmetin glucuronide is a known human metabolite of Tolmetin.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  托美丁葡糖苷酸 在 phosphate buffer 作用下， 反应 6.0h， 生成 D-吡喃葡萄糖醛酸 、 托麦汀
  参考文献：
  名称：

  Irreversible binding of tolmetin to macromolecules via its glucuronide: Binding to blood constituents, tissue homogenates and subcellular fractionsin vitro

  摘要：

  1. The degradation of tolmetin glucuronide (TG) in biological fluids and tissue homogenates appears to follow first-order kinetics and is quite rapid in plasma. TG degradation was minimized upon the addition of phenylmethylsulphonyl fluoride (PMSF) and 1,4-saccharolactone, suggesting that the majority of the degradation may be enzymatic, rather than chemical hydrolysis.2. Irreversible binding via TG was detected in all tissue preparations examined. Upon addition of an inhibitor of esterases (PMSF) to human serum albumin (HSA) and plasma, binding was extensive (2.5%) and the extent of binding was both time- and pH-dependent. Similar extents of binding were obtained with most tissue homogenates, except for spleen and intestine which exhibited much lower binding.3. Incubation of TG with microsomal protein from sheep and rat yielded no significant differences. Incubations of tolmetin (T) and TG with microsomes, as well as tissue homogenates, indicates that irreversible binding occurs only in the presence of TG.4. Irreversible binding occurred in all of the blood constituents, the highest extent with haemolyzed erythrocytes. The extent of binding was 15 times higher in disrupted versus intact red blood cells, suggesting a correlation between the extent of binding and the overall exposure of TG to the macromolecules to which it may bind irreversibly.

  DOI：

  10.3109/00498259409043252