4-nitrosoclenbuterol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-nitrosoclenbuterol
• 英文别名: 2-(Tert-butylamino)-1-(3,5-dichloro-4-nitrosophenyl)ethanol；2-(tert-butylamino)-1-(3,5-dichloro-4-nitrosophenyl)ethanol
• 化学式: C₁₂H₁₆Cl₂N₂O₂
• 分子量: 291.177
• InChiKey: YPEUFDCZPACYNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  克仑特罗 在 过氧乙酸 、 锌 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 4-nitrosoclenbuterol
  参考文献：
  名称：

  Evidence for a New and Major Metabolic Pathway of Clenbuterol Involving in Vivo Formation of an N-Hydroxyarylamine

  摘要：

  Clenbuterol is a beta-adrenergic agonist widely but illegally used in cattle as a growth promoter. The metabolic fate of this drug remains unknown in the main target species, i.e. the bovine, and only limited data have been published concerning its biotransformations in laboratory animals. A metabolic study has been carried out in the rat using H-3- and C-14-labeled clenbuterol. Urine appeared to be the major excretion pathway. Using a soft technique for urine preparation, extraction, and purification, as well as adequate analytical tools in order to preserve labile metabolites, N-oxidation products of the parental drug on the primary amine function were identified for the first time. Clenbuterol hydroxylamine was the major compound, but 4-nitroclenbuterol was also detected. The metabolic pathway leading to the formation of clenbuterol hydroxylamine prevails at high dosages. Clenbuterol hydroxylamine (but not 4-nitroclenbuterol) was also formed extensively when the drug was incubated with rat liver microsomal fractions in aerobic conditions. It is concluded that oxide reduction reactions during urine preparation have previously impaired the identification of this toxicologically important clenbuterol metabolic route.

  DOI：

  10.1021/tx960143s

文献信息

• Evidence for a New and Major Metabolic Pathway of Clenbuterol Involving <i>in Vivo</i> Formation of an <i>N</i>-Hydroxyarylamine
  作者：Daniel Zalko、Laurent Debrauwer、Georges Bories、Jacques Tulliez

  DOI：10.1021/tx960143s

  日期：1997.2.1

  Clenbuterol is a beta-adrenergic agonist widely but illegally used in cattle as a growth promoter. The metabolic fate of this drug remains unknown in the main target species, i.e. the bovine, and only limited data have been published concerning its biotransformations in laboratory animals. A metabolic study has been carried out in the rat using H-3- and C-14-labeled clenbuterol. Urine appeared to be the major excretion pathway. Using a soft technique for urine preparation, extraction, and purification, as well as adequate analytical tools in order to preserve labile metabolites, N-oxidation products of the parental drug on the primary amine function were identified for the first time. Clenbuterol hydroxylamine was the major compound, but 4-nitroclenbuterol was also detected. The metabolic pathway leading to the formation of clenbuterol hydroxylamine prevails at high dosages. Clenbuterol hydroxylamine (but not 4-nitroclenbuterol) was also formed extensively when the drug was incubated with rat liver microsomal fractions in aerobic conditions. It is concluded that oxide reduction reactions during urine preparation have previously impaired the identification of this toxicologically important clenbuterol metabolic route.