向内-N-(9-甲基-9-氮杂双环[3.3.1]壬烷-3基)-1-甲基-1H-吲唑-3-甲酰胺 | 160177-67-3

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 向内-N-(9-甲基-9-氮杂双环[3.3.1]壬烷-3基)-1-甲基-1H-吲唑-3-甲酰胺
• 中文别名: 9'-去甲格拉司琼；格拉司琼杂质C
• 英文名称: 1-Methyl-1H-indazole-3-carboxylic acid (9-aza-bicyclo[3.3.1]non-3-yl)-amide
• 英文别名: 9'-Desmethyl Granisetron (Granisetron Impurity C)；N-(9-azabicyclo[3.3.1]nonan-3-yl)-1-methylindazole-3-carboxamide
• CAS: 160177-67-3
• 化学式: C₁₇H₂₂N₄O
• 分子量: 298.388
• InChiKey: VIGVTDRZHFWDBM-UHFFFAOYSA-N

物化性质

• 熔点：
  167-169°C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  59
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  [11C]methyl iodide 、 向内-N-(9-甲基-9-氮杂双环[3.3.1]壬烷-3基)-1-甲基-1H-吲唑-3-甲酰胺 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.1h， 以45%的产率得到[11C]granisetron
  参考文献：
  名称：

  Synthesis of [11C]granisetron, a possible positron emission tomography ligand for 5-HT3 receptor studies

  摘要：

  [C-11] Granisetron, a selective 5-HT3 antagonist, was synthesized by N-alkylation of the desmethyl compound using [C-11] methyl iodide as the labelling agent in a total synthesis time of 40 min, including semi-preparative HPLC purification. Approximately 40 mCi (1.5 GBq) of the radioligand was obtained with a specific activity of 200-250 mCi/mu mol (7.4-9 GBq/mu mol). Chemical (greater than or equal to 96%) and radiochemical purity (greater than or equal to 99%) were determined using analytical HPLC.

  DOI：

  10.1002/(sici)1099-1344(199803)41:3<171::aid-jlcr66>3.0.co;2-f
• 作为产物：
  描述：

  granisetron 在 盐酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.5h， 生成 向内-N-(9-甲基-9-氮杂双环[3.3.1]壬烷-3基)-1-甲基-1H-吲唑-3-甲酰胺
  参考文献：
  名称：

  Synthesis of [11C]granisetron, a possible positron emission tomography ligand for 5-HT3 receptor studies

  摘要：

  [C-11] Granisetron, a selective 5-HT3 antagonist, was synthesized by N-alkylation of the desmethyl compound using [C-11] methyl iodide as the labelling agent in a total synthesis time of 40 min, including semi-preparative HPLC purification. Approximately 40 mCi (1.5 GBq) of the radioligand was obtained with a specific activity of 200-250 mCi/mu mol (7.4-9 GBq/mu mol). Chemical (greater than or equal to 96%) and radiochemical purity (greater than or equal to 99%) were determined using analytical HPLC.

  DOI：

  10.1002/(sici)1099-1344(199803)41:3<171::aid-jlcr66>3.0.co;2-f

文献信息

• 5-HT 3? RECEPTOR ANTAGONISTS FOR TREATMENT OF COUGH AND BRONCHOCONSTRICTION
  申请人：BEECHAM GROUP PLC

  公开号：EP0340270B1

  公开（公告）日：1992-07-15
• NOVEL AEROSOL FORMULATIONS OF GRANISETRON AND USES THEREOF
  申请人：LUXENA PHARMACEUTICALS, INC.

  公开号：US20200085801A1

  公开（公告）日：2020-03-19

  Aerosol formulations of granisetron useful for pulmonary delivery are provided. The formulations are useful in the reduction, elimination or prevention of nausea and vomiting associated with chemotherapy, radiation therapy, and surgery. Also provided are novel methods to treat chemotherapy-induced nausea and vomiting (CINV), radiation-induced nausea and vomiting (RINV), and post-operative nausea and vomiting (PONV) using the inhalation formulations.
• Synthesis of [11C]granisetron, a possible positron emission tomography ligand for 5-HT3 receptor studies
  作者：I. Vandersteene、K. Audenaert、G. Slegers、R. Dierckx

  DOI：10.1002/(sici)1099-1344(199803)41:3<171::aid-jlcr66>3.0.co;2-f

  日期：1998.3

  [C-11] Granisetron, a selective 5-HT3 antagonist, was synthesized by N-alkylation of the desmethyl compound using [C-11] methyl iodide as the labelling agent in a total synthesis time of 40 min, including semi-preparative HPLC purification. Approximately 40 mCi (1.5 GBq) of the radioligand was obtained with a specific activity of 200-250 mCi/mu mol (7.4-9 GBq/mu mol). Chemical (greater than or equal to 96%) and radiochemical purity (greater than or equal to 99%) were determined using analytical HPLC.