Oxalsaeure-mono(2-acetyl-2-methyl-1-phenyl)hydrazid | 38988-02-2

• 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: Oxalsaeure-mono(2-acetyl-2-methyl-1-phenyl)hydrazid
• 英文别名: oxalic acid-(N'-acetyl-N'-methyl-N-phenyl)hydrazide；2-(N-[acetyl(methyl)amino]anilino)-2-oxoacetic acid
• CAS: 38988-02-2
• 化学式: C₁₁H₁₂N₂O₄
• 分子量: 236.227
• InChiKey: KHSFDWLKYABAGT-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120 °C(Solv: toluene (108-88-3))
• 沸点：
  383.0±25.0 °C(Predicted)
• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  77.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 Oxalsaeure-mono(2-acetyl-2-methyl-1-phenyl)hydrazid 在 重氮甲烷 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.33h， 以100%的产率得到methyl-2-(N'-acetyl-N'-methyl-N-phenyl)-hydrazino-2-oxo-acetate
  参考文献：
  名称：

  Characterization of oxalic acid derivatives as new metabolites of metamizol (dipyrone) in incubated hen's egg and human

  摘要：

  Metamizol (dipyrone, 1), a widely used drug with effective analgesic and antispasmodic properties, shows severe side effects like agranulocytosis and anaphylactic shock reactions, the reasons of which are not known until today. After oral administration 1 is completely metabolized. All hitherto known metabolites have an intact pyrazolinone ring structure like the parent compound and are completely extractable from urine with polar organic solvents. However, only a fractional amount of the applied dosage can be recovered by this procedure. To clarify the reason of this deficit of unknown metabolites we followed the hypothesis of oxidative rupture of the heterocyclic ring during metabolism of 1. on the basis of former in vitro results we now were able to identify in quality three oxalic acid derivatives and one acetic acid phenylhydrazide as new metabolites of metamizol in the allantoic fluid (AF) of incubated hen's eggs as well as in human urine by means of GC-MS analysis and comparison with unequivocally synthesized authentic reference compounds. Whereas the oxamazide 7, the phenylhydrazide 8 and N-methyloxamic acid 9 are only present in trace concentrations and therefore cannot account for the deficit in the balance of metabolites, the oxalic acid monohydrazide 11 seems to be excreted in higher amount. But quantitative determination of this new metabolite would be required to answer the open questions concerning the biotransformation of metamizol and thereby to detect new facts about mode of action and side effects of this drug. (c) 2005 Elsevier B.V.All rights reserved.

  DOI：

  10.1016/j.ejps.2005.11.010
• 作为产物：
  描述：

  metamizol 在 双氧水 作用下， 反应 0.08h， 以79%的产率得到Oxalsaeure-mono(2-acetyl-2-methyl-1-phenyl)hydrazid
  参考文献：
  名称：

  Weber; Bresser, Pharmazie, 1996, vol. 51, # 3, p. 152 - 155

  摘要：

  DOI：

文献信息

• Oxidative Ringöffnung von 3(2H)-Pyrazolonen mit Periodat
  作者：Horst Weber、Eva Wollenberg

  DOI：10.1002/ardp.19883210912

  日期：——

  gegen Singulett‐Sauerstoff stabil. Keine Unterschiede zeigen die Titelverbindungen 1, 3 und 5 bei der Reaktion mit Natriummetaperiodat, wobei unter Ringöffnung die Oxidationsprodukte 2, 4 und 6 gebildet werden. Die 1H‐ und 13C‐NMR‐Spektren von 4 zeigen ähnlich wie bei 2 das Vorliegen rotamerer Formen bei Raumtemperatur.

  与氨基吡唑啉酮 1 相比，吡唑啉酮 3 和 5 对单线态氧稳定。标题化合物 1、3 和 5 在与偏高碘酸钠的反应中没有差异，氧化产物 2、4 和 6 开环形成。与 2 类似，4 的 1H 和 13C NMR 谱表明在室温下存在旋转异构形式。
• Characterization of oxalic acid derivatives as new metabolites of metamizol (dipyrone) in incubated hen's egg and human
  作者：Julia C. Wessel、Magdalena Matyja、Michael Neugebauer、Heiko Kiefer、Thomas Daldrup、Fuad A. Tarbah、Horst Weber

  DOI：10.1016/j.ejps.2005.11.010

  日期：2006.5

  Metamizol (dipyrone, 1), a widely used drug with effective analgesic and antispasmodic properties, shows severe side effects like agranulocytosis and anaphylactic shock reactions, the reasons of which are not known until today. After oral administration 1 is completely metabolized. All hitherto known metabolites have an intact pyrazolinone ring structure like the parent compound and are completely extractable from urine with polar organic solvents. However, only a fractional amount of the applied dosage can be recovered by this procedure. To clarify the reason of this deficit of unknown metabolites we followed the hypothesis of oxidative rupture of the heterocyclic ring during metabolism of 1. on the basis of former in vitro results we now were able to identify in quality three oxalic acid derivatives and one acetic acid phenylhydrazide as new metabolites of metamizol in the allantoic fluid (AF) of incubated hen's eggs as well as in human urine by means of GC-MS analysis and comparison with unequivocally synthesized authentic reference compounds. Whereas the oxamazide 7, the phenylhydrazide 8 and N-methyloxamic acid 9 are only present in trace concentrations and therefore cannot account for the deficit in the balance of metabolites, the oxalic acid monohydrazide 11 seems to be excreted in higher amount. But quantitative determination of this new metabolite would be required to answer the open questions concerning the biotransformation of metamizol and thereby to detect new facts about mode of action and side effects of this drug. (c) 2005 Elsevier B.V.All rights reserved.
• Weber; Bresser, Pharmazie, 1996, vol. 51, # 3, p. 152 - 155
  作者：Weber、Bresser

  DOI：——

  日期：——