Dihydrocodeine-6-glucuronide | 88480-40-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: Dihydrocodeine-6-glucuronide
• 英文别名: (2S,3S,4S,5R,6R)-6-[[(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 88480-40-4
• 化学式: C₂₄H₃₁NO₉
• 分子量: 477.511
• InChiKey: WBVBRJPPWYRNPU-HSCJLHHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  双氢可待因 在 barium dihydroxide 、 sodium methylate 、 silver carbonate 作用下， 以 甲醇 、 苯 为溶剂， 反应 10.67h， 生成 Dihydrocodeine-6-glucuronide
  参考文献：
  名称：

  Metabolism and pharmacokinetics of dihydrocodeine in dog

  摘要：

  1. The metabolism and pharmacokinetics of dihydrocodeine have been studied in dog. Urinary metabolites after oral administration of dihydrocodeine were identified using hplc with diode-array and ms.2. In urine, dihydronorcodeine, dihydromorphine and dihydrocodeine glucuronide were identified in comparison with their authentic standards, and dihydronorcodeine 6-glucuronide also appeared to be excreted as a metabolite.3. The major urinary metabolite was dihydrocodeine glucuronide, recovered as 49% of the dose, and other metabolites were found to be 0.1-3%, 24h after 3 mg/kg oral administration of dihydrocodeine. Plasma concentrations of unchanged dihydrocodeine were significantly lower after oral rather than intramuscular administration; the maximum concentrations were 40 and 549 ng/ml after oral and intramuscular administration, respectively. This suggests that dihydrocodeine was metabolized via a hepatic first-pass effect after oral administration.4. Overall, our results indicate that the metabolic pathways of dihydrocodeine in dog were similar to that of codeine metabolism in animals and man.

  DOI：

  10.3109/00498259409043262

文献信息

• Metabolism and pharmacokinetics of dihydrocodeine in dog
  作者：M. Konishi、Y. Shiono、M. Ohno、H. Takahashi、T. Aoki

  DOI：10.3109/00498259409043262

  日期：1994.1

  1. The metabolism and pharmacokinetics of dihydrocodeine have been studied in dog. Urinary metabolites after oral administration of dihydrocodeine were identified using hplc with diode-array and ms.2. In urine, dihydronorcodeine, dihydromorphine and dihydrocodeine glucuronide were identified in comparison with their authentic standards, and dihydronorcodeine 6-glucuronide also appeared to be excreted as a metabolite.3. The major urinary metabolite was dihydrocodeine glucuronide, recovered as 49% of the dose, and other metabolites were found to be 0.1-3%, 24h after 3 mg/kg oral administration of dihydrocodeine. Plasma concentrations of unchanged dihydrocodeine were significantly lower after oral rather than intramuscular administration; the maximum concentrations were 40 and 549 ng/ml after oral and intramuscular administration, respectively. This suggests that dihydrocodeine was metabolized via a hepatic first-pass effect after oral administration.4. Overall, our results indicate that the metabolic pathways of dihydrocodeine in dog were similar to that of codeine metabolism in animals and man.