lornoxicam ammonium salt | 1608472-18-9

• 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
• 英文名称: lornoxicam ammonium salt
• 英文别名: azanium;6-chloro-2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)thieno[2,3-e]thiazin-4-olate
• CAS: 1608472-18-9
• 化学式: C₁₃H₁₀ClN₃O₄S₂*H₃N
• 分子量: 388.856
• InChiKey: KBZKPSFBRKPGNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  氯诺昔康 在 ammonium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.75h， 以92%的产率得到lornoxicam ammonium salt
  参考文献：
  名称：

  Lornoxicam Salts: Crystal Structures, Conformations, and Solubility

  摘要：

  Lornoxicam (LXM), a nonsteroidal anti-inflammatory drug (NSAID), is an amphiprotic molecule that exists as a zwitterion in the solid state. The formation of two strong intramolecular N+-H center dot center dot center dot O and N-H center dot center dot center dot O- hydrogen bonds in a stable six-member ring geometry, S(6), renders this otherwise flexible molecule in a rigid conformation (conformer A). A salt screen of LXM was undertaken to improve drug solubility and to study different conformations of the molecule by varying the counterion. As an amphoteric molecule, LXM salts are both cationic (ammonia, piperazine) and anionic (hydrochloric acid, methanesulfonic acid). The crystal structures of these salts exhibit an intramolecular H bond with different conformations of LXM in the acid and base salts (conformations B and C). The conformational variability of LXM in acidic and basic salts is explained by steric and hydrogen bonding factors. All the new salts were characterized by spectroscopic, thermal, powder X-ray diffraction techniques and showed enhanced solubility compared to the free drug.

  DOI：

  10.1021/cg500231z