艾司西酞普兰 E | 63284-72-0

• 物质功能分类: 分析化学 - 对照品
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 艾司西酞普兰 E
• 中文别名: 西酞普兰USP相关物质E；艾司西酞普兰E；西酞普兰USP RC E
• 英文名称: Citalopram N-Oxide
• 英文别名: 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile N-oxide；3-[5-cyano-1-(4-fluorophenyl)-3H-2-benzofuran-1-yl]-N,N-dimethylpropan-1-amine oxide
• CAS: 63284-72-0
• 化学式: C₂₀H₂₁FN₂O₂
• 分子量: 340.397
• InChiKey: DIOGFDCEWUUSBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  91-93°C
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  4

ADMET

代谢

西酞普兰N-氧化物是西酞普兰的人类已知代谢物。

Citalopram N-oxide is a known human metabolite of Citalopram.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  西酞普兰 在 还原型辅酶Ⅰ 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1-(4-氟苯基)-1,3-二氢-1-[3-(甲基氨基)丙基]异苯并呋喃-5-甲腈 、 艾司西酞普兰 E
  参考文献：
  名称：

  Effect of CYP2D6 genetic polymorphism on the metabolism of citalopram in vitro

  摘要：

  Genetic polymorphisms of CYP2D6 significantly influence the efficacy and safety of some drugs, which might cause adverse effects and therapeutic failure. We aimed at investigating the role of CYP2D6 in the metabolism of citalopram and identifying the effect of 24 CYP2D6 allelic variants we found in Chinese Han population on the metabolism of citalopram in vitro. These CYP2D6 variants expressed by insect cells system were incubated with 10-1000 mu M citalopram for 30 min at 37 degrees C and the reaction was terminated by cooling to -80 degrees C immediately. Citalopram and its metabolites were analyzed by high-performance liquid chromatography (HPLC). The intrinsic clearance (V-max/K-m) values of the variants toward citalopram metabolites were significantly altered, 38-129% for demethylcitalopram and 13-138% for citalopram N-oxide when compared with CYP2D6*1. Most of the tested rare alleles exhibited significantly decreased values due to increased Km and/or decreased V-max values. We conclude that recombinant system could be used to investigate the enzymes involved in drug metabolism and these findings suggest that more attention should be paid to subjects carrying these CYP2D6 alleles when administering citalopram in the clinic. Copyright (C) 2016, The Japanese Society for the Study of Xenobiotics. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dmpk.2016.01.001

文献信息

• Citalopram Hydrobromide: degradation product characterization and a validated stability-indicating LC-UV method
  作者：Manav Sharma、Parikshit R Jawa、Ravinder S Gill、Gulshan Bansal

  DOI：10.1590/s0103-50532011000500005

  日期：——

  Five degradation products (I-V) of citalopram hydrobromide (CTL) were formed under different forced degradation conditions. Products I and II were formed under hydrolytic conditions while product III-V were formed under photolytic conditions. Products II and IV were found known impurities as citalopram carboxamide and citalopram N-oxide, respectively. Product I was found to be a new impurity which was characterized as 3-hydroxycitalopram N-oxide. The drug and all five degradation products were optimally resolved on a C(8) column with mobile phase composed of acetonitrile and ammonium acetate buffer (pH* 4.5) flowing at a rate of 0.50 mL min(-1). The method was linear, precise RSD < 3 (relative standard deviation) and accurate (recovery being 88-97%) in the concentration range of 5-500 mu g mL(-1) of citalopram. The limits of detection (LOD) and of quantitation (LOQ) were 1 mu g mL(-1) and 5 mu g mL(-1), respectively. The photodiode array (PDA) analysis of the degraded CTL solution containing the CTL and all five degradation products revealed each peak to be pure. Hence, the method was suggested to be stability-indicating.