水杨酰-甘氨酰-甘氨酸 | 5853-99-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 水杨酰-甘氨酰-甘氨酸
• 中文别名: 二苹果酸二氢钙
• 英文名称: salicyloylglycylglycine
• 英文别名: salicyl-glycylglycine；Salicoyl-glycyl-glycin；Salicyl-glycyl-glycine；2-[[2-[(2-hydroxybenzoyl)amino]acetyl]amino]acetic acid
• CAS: 5853-99-6
• 化学式: C₁₁H₁₂N₂O₅
• mdl: MFCD03130028
• 分子量: 252.227
• InChiKey: YTOBMCBKPPVZEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  acetylsalicyloylglycylglycine 在 盐酸 作用下， 反应 1.0h， 生成 水杨酰-甘氨酰-甘氨酸
  参考文献：
  名称：

  Mukherjee; Chattopadhyay, Journal of the Indian Chemical Society, 1991, vol. 68, # 12, p. 639 - 642

  摘要：

  DOI：

文献信息

• A Novel Prodrug of Salicylic Acid, Salicylic Acid-glycylglycine Conjugate, Utilizing the Hydrolysis in Rabbit Intestinal Microorganisms
  作者：Junzo Nakamura、Kumiko Asai、Koyo Nishida、Hitoshi Sasaki

  DOI：10.1111/j.2042-7158.1992.tb05505.x

  日期：2011.4.12

  The hydrolysis of salicylic acid-glycylglycine conjugate (salicyl-glycylglycine) following oral, intravenous, intracaecal and rectal administration (434, 72, 36 and 36 μmol kg−1, respectively: equivalent to salicylic acid) was examined in rabbits to develop a novel prodrug of salicylic acid. Salicylic acid was detected in the blood 2 h after oral administration of salicyl-glycylglycine and it reached a maximum level (55·6 μg mL−1) at 15 h, whereas a small amount of salicyl-glycylglycine was found in the blood. In contrast, unchanged salicyl-glycylglycine was found mainly in the blood following its intravenous administration, suggesting the involvement of presystemic deconjugation in the hydrolysis of salicyl-glycylglycine. Immediate and very extensive salicyclic acid formation in the caecum was observed following intracaecal administration of salicyl-glycylglycine, suggesting that the intestinal microorganisms were responsible for the biotransformation of this compound. In-vitro incubation of salicyl-glycylglycine with caecal content showed that salicyl-glycylglycine was hydrolysed efficiently in the caecum. Consequently, the blood concentration of salicylic acid was prolonged extensively following rectal administration of salicylglycylglycine, indicating the usefulness of salicyl-glycylglycine as a prodrug of salicylic acid.

  将水杨酸-甘氨酰甘氨酸结合物（水杨酸-甘氨酰甘氨酸）在兔子体内经口、静脉、盲肠和直肠给药（分别为434、72、36和36μmol kg−1，相当于水杨酸）后的水解作用进行了研究，以开发水杨酸的新型前药。水杨酸在口服水杨酸-甘氨酰甘氨酸后的2小时内被检测到血液中，并在15小时达到最高水平（55.6μg mL−1），而血液中发现了少量水杨酸-甘氨酰甘氨酸。相反，静脉给药后，血液中主要发现未改变的水杨酸-甘氨酰甘氨酸，表明预系统脱共轭参与了水杨酸-甘氨酰甘氨酸的水解。盲肠给药后立即在盲肠内观察到水杨酸的形成，表明肠道微生物负责这种化合物的生物转化。体外培养水杨酸-甘氨酰甘氨酸与盲肠内容物显示水杨酸-甘氨酰甘氨酸在盲肠中被有效水解。因此，直肠给药后水杨酸的血液浓度显著延长，表明水杨酸-甘氨酰甘氨酸作为水杨酸的前药具有实用性。
• Mukherjee; Chattopadhyay, Journal of the Indian Chemical Society, 1991, vol. 68, # 12, p. 639 - 642
  作者：Mukherjee、Chattopadhyay

  DOI：——

  日期：——