Isolation and characterization of impurities in docetaxel

During the process development of docetaxel, two polar impurities (Impurities I and II) and two non-polar impurities (Impurities III and IV) were detected by high performance liquid chromatography (HPLC). All the impurities were isolated by Medium Pressure Liquid Chromatography (MPLC). The Impuritie...

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Bibliographic Details
Published in:Journal of pharmaceutical and biomedical analysis 2006-02, Vol.40 (3), p.614-622
Main Authors: Vasu Dev, R., Moses Babu, J., Vyas, K., Sai Ram, P., Ramachandra, P., Sekhar, N.M., Mohan Reddy, D.N., Srinivasa Rao, N.
Format: Article
Language:English
Subjects:
Antineoplastic Agents, Phytogenic - analysis
Characterization
Chromatography, High Pressure Liquid
Docetaxel
Drug Contamination
Identification
Impurity
Liquid chromatography-mass spectrometry
Magnetic Resonance Spectroscopy
Mass Spectrometry
Models, Molecular
Molecular Conformation
MPLC
Spectroscopy
Taxoids - analysis
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Description
Summary:During the process development of docetaxel, two polar impurities (Impurities I and II) and two non-polar impurities (Impurities III and IV) were detected by high performance liquid chromatography (HPLC). All the impurities were isolated by Medium Pressure Liquid Chromatography (MPLC). The Impurities I, II, III and IV were identified as 13-[(4 S,5 R)-2-oxo-4-phenyl-oxazolidine-5-carboxy]-10-deacetyl baccatin III ester, 2′-epi docetaxel, 7-epi docetaxel and 13-[(4 S,5 R)-2-oxo-4-phenyl-oxazolidine-3,5-dicarboxyl-3-tert-butyl)]-10-deacetyl baccatin III ester, respectively, based on one- (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) spectroscopy data. The Impurity IV was crystallized and the structure was solved by single crystal X-ray diffraction (XRD). Two impurities (Impurities II and III) were found to be process related, while the remaining two impurities (Impurities I and IV) turned out to be isomers. The formation of these impurities was discussed.
ISSN:0731-7085
1873-264X
DOI:10.1016/j.jpba.2005.10.037