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Characterization, Quantification and Compound-specific Isotopic Analysis of Pyrogenic Carbon Using Benzene Polycarboxylic Acids BPCA
Published on: May 16, 2016
Isolation, structural characterization and quantification of impurities in bupivacaine
Pengjun Cai1, Yanhua Su1, Yue Li2
1School of Chinese Materia Medica, Nanjing University of Chinese Medicine, 138 Xianlin Avenue, Nanjing, Jiangsu 210023, China; Analytical Research Center for Organic and Biological Molecules, CAS Key Laboratory of Receptor Research, State Key Laboratory of Drug Research, Shanghai Institute of Materia Media, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.
Bupivacaine degrades under accelerated conditions, forming two impurities identified by LC-MS. A validated LC-MS method was developed for quantifying these bupivacaine degradation products, aiding quality control.
Area of Science:
- Analytical Chemistry
- Pharmaceutical Science
- Organic Chemistry
Background:
- Bupivacaine stability is crucial for pharmaceutical formulations.
- Accelerated storage conditions can reveal drug degradation pathways.
- Identifying and quantifying drug impurities ensures product safety and efficacy.
Purpose of the Study:
- To identify and characterize degradation impurities of bupivacaine.
- To develop and validate a quantitative analytical method for these impurities.
- To establish quality control measures for bupivacaine formulations.
Main Methods:
- High-performance liquid chromatography-mass spectrometry (LC-MS) for impurity detection.
- Semipreparative chromatography for impurity isolation and purification.
- High-resolution mass spectrometry (HR-MSMS) and Nuclear Magnetic Resonance (NMR) spectroscopy for structural elucidation.
- Single crystal X-ray diffraction for stereochemical characterization.
- Validated LC-MS method for quantitative analysis.
Main Results:
- Two bupivacaine degradation impurities (RS1 and RS2) were identified and structurally characterized.
- Stereo structures of the impurities were confirmed via X-ray diffraction.
- A sensitive and validated LC-MS method was established with low limits of quantitation (0.89 ng for RS1, 0.65 ng for RS2).
- The method demonstrated high accuracy (90-108% recovery) and precision (<5.0% RSD).
Conclusions:
- Bupivacaine exhibits instability under accelerated storage conditions (40°C, 75% RH).
- The developed LC-MS method is suitable for routine quality control of bupivacaine and its pharmaceutical products.
- Comprehensive structural characterization aids in understanding bupivacaine degradation mechanisms.
