Identification, characterization and HPLC quantification of formulation-related impurities of honokiol, an antitumor natural drug candidate in clinical trials

J Pharm Biomed Anal. 2018 May 10:153:186-192. doi: 10.1016/j.jpba.2018.02.033. Epub 2018 Feb 21.

Abstract

Natural products and their derivatives have historically been invaluable as a source of therapeutic agents. Honokiol, as a well-known natural product in Chinese herbal medicine Houpu, is finally being studied in a Phase I clinical trial (CTR20170822) in patients with Advanced Non-Small Cell Lung Cancer (NSCLS) in China this year. During the honokiol liposome formulation process, five major impurities were present in the range of 0.05-0.1% based on the HPLC analysis. These five major impurities were obtained from the forced degradation product of honokiol through countercurrent chromatography and prep-HPLC. The structure were elucidated with 1H NMR, 13C NMR, 2D NMR and MS spectral data. The proposed HPLC method was validated for specificity, linearity (concentration range 0.01-1.62, 0.003-0.96, 0.05-7.98, 0.04-6.52, 0.03-5.18 μg/ml for impurities I-V respectively, R2 > 0.9988), accuracy (99.11-100.67%), precision (CV < 1.6%), and sensitivity (LOD 3.3, 0.1, 16.7, 13.3, 10.0 ng/ml for impurities I-V respectively). The validated method was employed in the further study of the honokiol drug substance.

Keywords: Formulation-related impurities; Honokiol; Natural products; Structure identification; Validation.

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Biological Products / chemistry
  • Biphenyl Compounds / chemistry*
  • China
  • Chromatography, High Pressure Liquid / methods
  • Clinical Trials as Topic
  • Drug Contamination
  • Drugs, Chinese Herbal / analysis
  • Lignans / chemistry*
  • Magnetic Resonance Spectroscopy / methods
  • Reproducibility of Results
  • Sensitivity and Specificity
  • Tandem Mass Spectrometry / methods

Substances

  • Antineoplastic Agents
  • Biological Products
  • Biphenyl Compounds
  • Drugs, Chinese Herbal
  • Lignans
  • liposomal honokiol
  • honokiol