呋塞米杂质07 | 133989-65-8

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 呋塞米杂质07
• 英文名称: 4-hydroxy-N-furfuryl-5-sulfamoylanthranilic acid
• 英文别名: 2-(furan-2-ylmethylamino)-4-hydroxy-5-sulfamoylbenzoic acid
• CAS: 133989-65-8
• 化学式: C₁₂H₁₂N₂O₆S
• 分子量: 312.303
• InChiKey: QVCDKKKFLHOJJD-UHFFFAOYSA-N

物化性质

• 沸点：
  599.8±60.0 °C(Predicted)
• 密度：
  1.624±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  呋塞米 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 呋塞米杂质07
  参考文献：
  名称：

  Studies on the photolysis and hydrolysis of furosemide in aqueous solution.

  摘要：

  在缓冲溶液（pH 值介于 1.2 和 12.0 之间）中研究了呋塞米的光解和水解。光解实验在室温下进行，以日光灯[○！R]或荧光灯作为人工光源，以直射和间接阳光作为自然光源，并通过改变光照强度。研究发现，在人工光源和自然光源下，呋塞米的光解都遵循明显的一阶动力学。在酸性介质中，呋塞米的光解速率大于在中性或碱性介质中的光解速率。呋塞米光解的 pH 值-速率曲线表明，离子化呋塞米的光解速率远大于离子化呋塞米的光解速率。在 37°C 的暗室中进行了呋塞米的水解实验。实验还发现，呋塞米的水解遵循明显的一阶动力学。呋塞米在中性或碱性溶液中很稳定。在 pH 值低于 3 的酸性介质中，呋塞米的水解是由氢离子催化的，酸催化速率常数为 0.893 M-1-h-1。

  DOI：

  10.1248/cpb.39.454

文献信息

• Identification of Furosemide Photodegradation Products in Water–Acetonitrile Mixture
  作者：Shinji Katsura、Nobuo Yamada、Atsushi Nakashima、Sumihiro Shiraishi、Takayuki Furuishi、Haruhisa Ueda

  DOI：10.1248/cpb.c15-00122

  日期：——

  The aim of this study was to identify the chemical structure of the photodegradation products of furosemide in a water–acetonitrile mixture (1 : 1). Furosemide solution was irradiated with a D65 fluorescent lamp and the products were isolated by preparative HPLC. The fractions were evaporated to dryness in vacuo. The purity of the photodegradation products was measured by HPLC. The purity of products 1, 3, and 4 was greater than 90%, whereas that of product 2 was 13%, therefore, photodegradation product 2 was unstable. We identified photodegradation products 1 and 3 as 4-chloro-5-sulfamoylanthranilic acid and 4-hydroxy-N-furfuryl-5-sulfamoylanthranilic acid, respectively, by LC/MS and NMR. Additionally, we assumed that photodegradation product 4 was methyl 2-((furan-2-ylmethyl)amino)-4-hydroxy-3-(methyleneamino)-5-sulfamoylbenzoate by LC/MS and NMR. This showed that furosemide underwent hydrolysis and substitution, and reacted with the acetonitrile under the light of a D65 fluorescent lamp. We were furthermore able to determine the elution times of the photodegradation products of furosemide by applying the Japanese Pharmacopoeia chromatographic method for related substances to the isolated products.

  本研究的目的是确定水-乙腈混合物 (1 : 1) 中呋塞米光降解产物的化学结构。用D65荧光灯照射呋塞米溶液，通过制备型HPLC分离产物。将级分真空蒸发至干。通过HPLC测量光降解产物的纯度。产物1、3、4的纯度均大于90%，而产物2的纯度为13%，因此光降解产物2不稳定。我们通过LC/MS和NMR鉴定光降解产物1和3分别为4-氯-5-氨磺酰邻氨基苯甲酸和4-羟基-N-糠基-5-氨磺酰邻氨基苯甲酸。此外，通过LC/MS和NMR，我们假设光降解产物4是2-((呋喃-2-基甲基)氨基)-4-羟基-3-(亚甲基氨基)-5-氨磺酰基苯甲酸甲酯。这表明呋塞米在D65荧光灯的照射下发生水解和取代，并与乙腈发生反应。此外，我们还通过对分离产物应用日本药典相关物质色谱方法测定了呋塞米光降解产物的洗脱时间。
• Studies on the photolysis and hydrolysis of furosemide in aqueous solution.
  作者：Naomi YAGI、Harumi KENMOTSU、Hitoshi SEKIKAWA、Masahiko TAKADA

  DOI：10.1248/cpb.39.454

  日期：——

  Photolysis and hydrolysis of furosemide were studied in buffere solutions (pH between 1.2 and 12.0). Photolysis experiments were made at room temperature under a Daylight lamp[○!R] or fluorescent lamps as artificial light sources and direct and indirect sunlight as natural light sources by changing the strength of illumination. The photolysis of furosemide was found to follow apparent first-order kinetics under both artificial and natural light sources. In acidic media, the rate of photolysis of furosemide was larger than those in neutral or alkaline media. The pH-rate profile for the photolysis of furosemide indicated that the rate of photolysis of unionized furosemide was much larger than that of ionized furosemide. A hydrolysis experiment of furosemide was made at 37°C in the darkened room. The hydrolysis of furosemide was also found to follow apparent first-order kinetics. Furosemide was stable in neutral or alkaline solutions. In acidic media below pH 3, hydrolysis of furosemide was found to be catalyzed by hydrogen ion with an acid catalyzed rate constant of 0.893 M-1·h-1.

  在缓冲溶液（pH 值介于 1.2 和 12.0 之间）中研究了呋塞米的光解和水解。光解实验在室温下进行，以日光灯[○！R]或荧光灯作为人工光源，以直射和间接阳光作为自然光源，并通过改变光照强度。研究发现，在人工光源和自然光源下，呋塞米的光解都遵循明显的一阶动力学。在酸性介质中，呋塞米的光解速率大于在中性或碱性介质中的光解速率。呋塞米光解的 pH 值-速率曲线表明，离子化呋塞米的光解速率远大于离子化呋塞米的光解速率。在 37°C 的暗室中进行了呋塞米的水解实验。实验还发现，呋塞米的水解遵循明显的一阶动力学。呋塞米在中性或碱性溶液中很稳定。在 pH 值低于 3 的酸性介质中，呋塞米的水解是由氢离子催化的，酸催化速率常数为 0.893 M-1-h-1。