Analytical approaches for the detection of epoxides and hydroperoxides in active pharmaceutical ingredients, drug products and herbals

Journal of Pharmaceutical and Biomedical Analysis

Volumn 51, Issue 5, 2010, Pages 1015-1023

  Elder, D P ^a   Snodin, D ^b   Teasdale, A ^c  

^a GLAXOSMITHKLINE   (United Kingdom)

^b PAREXEL INTERNATIONAL   (United States)

^c ASTRAZENECA   (United Kingdom)

Author keywords

Chromatography; Epoxide; Genotoxic; Herbal; Hydroperoxide

Indexed keywords

2 CHLORO 5A,6,7,8,9,9A HEXAHYDRO N (3 QUINUCLIDINYL)DIBENZOFURAN 4 CARBOXAMIDE; ACEBUTOLOL; ALMOKALANT; ATENOLOL; ATORVASTATIN; BENZYL ALCOHOL; BETAMETHASONE; BETAXOLOL; BICALUTAMIDE; CARAPA GUIANENSIS EXTRACT; CARTEOLOL; CELIPROLOL; COLECALCIFEROL; CORTICOSTEROID DERIVATIVE; DEXAMETHASONE; EPOXIDE; FLUOCINOLONE ACETONIDE; HYDROPEROXIDE DERIVATIVE; HYPERICIUM PERFORATUM EXTRACT; LOTEPREDNOL ETABONATE; MOMETASONE FUROATE; NADOLOL; PLANT EXTRACT; PROPAFENONE; PSEUDOMONIC ACID; RETINOL; STAVUDINE; TRIPTERYGIUM WILFORDII EXTRACT; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINCRISTINE SULFATE;

CAPILLARY ZONE ELECTROPHORESIS; CARAPA GUIANENSIS; CHEMICAL ANALYSIS; DRUG IMPURITY; GAS LIQUID CHROMATOGRAPHY; GENOTOXICITY; HERBAL MEDICINE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH PERFORMANCE THIN LAYER CHROMATOGRAPHY; HYPERICIUM PERFORATUM; MEDICINAL PLANT; MICELLAR ELECTROKINETIC CHROMATOGRAPHY; PRIORITY JOURNAL; REVIEW; RISK ASSESSMENT; THIN LAYER CHROMATOGRAPHY;

CHEMISTRY TECHNIQUES, ANALYTICAL; DRUG CONTAMINATION; EPOXY COMPOUNDS; HUMANS; HYDROGEN PEROXIDE; MUTAGENS; PEROXIDES; PLANT PREPARATIONS; REPRODUCIBILITY OF RESULTS; RISK ASSESSMENT; TECHNOLOGY, PHARMACEUTICAL;

EID: 73049116885     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2009.11.023     Document Type: Review

References (51)

1. Guideline on the Limits of Genotoxic Impurities (2006), Committee for Medicinal Products (CHMP), European Medicines Agency, London 28 June (CPMP/SWP/5199/02, EMEA/CHMP/QWP/251344/2006)
2. Elder D.P., Teasdale A., and Lipczynski A.M. The control and analysis of alkyl esters of alkyl and aryl sulphonic acids in novel active pharmaceutical ingredients (APIs). J. Pharm. Biomed. Anal. 46 (2008) 1-8
3. Elder D.P., Teasdale A., and Lipczynski A.M. The control and analysis of alkyl and benzyl halides and other related reactive organohalides as potential genotoxic impurities in active pharmaceutical ingredients (APIs). J. Pharm. Biomed. Anal. 48 (2008) 497-507
4. Dobo K.L., Greene N., Cyr M.O., Caron S., and Ku W.W. The application of structure-based assessment to support safety and chemical diligence to manage genotoxic impurities in active pharmaceutical ingredients during drug development. Regul. Toxicol. Pharm. 44 (2006) 282-293
5. Harmon P.A., Kosuda K., Nelson E., Mowery M., and Reed R.A. A novel peroxy radical based oxidative stressing system for ranking the oxidizability of drug substances. J. Pharm. Sci. 95 (2006) 2014-2028
6. Nakamura T., and Maeda H. A simple assay for lipid hydroperoxides based on triphenylphosphine oxidation and high-performance liquid chromatography. Lipids 26 (1991) 765-768
7. Spangler M., and Mularz E. A validated, stability-indicating method for the assay of dexamethasone in drug substance and drug product analyses, and the assay of preservatives in drug product. Chromatography 54 (2001) 329-334
8. Yasueda S.I., Higashiyama M., Shirasaki Y., Inada K., and Ohtori A. An HPLC method to evaluate purity of a steroidal dug, loteprednol etabonate. J. Pharm. Biomed. Anal. 36 (2001) 309-316
9. Xiao K.P., Xiong Y., Liu F.Z., and Rustum A.M. Efficient method development strategy for challenging separation of pharmaceutical molecules using advanced chromatographic techniques. J. Chromatogr. A 1163 (2007) 145-156
10. Lacroix P.M., Curran N.M., and Lovering E.G. Nadalol: high-pressure liquid chromatographic methods for assay racemate composition and related compounds. J. Pharm. Biomed. Anal. 10 (1992) 917-924
11. Rao R.N., Raju A.N., and Narshima R. Isolation and characterization of process related impurities an degradation products of bicalutamide and development of RP-HPLC method for impurity profile study. J. Pharm. Biomed. Anal. 46 (2008) 505-519
12. Won C.H., Tang S.-Y., and Strohbeck C.L. Photolytic and oxidative degradation of an antiemetic agent, RG12915. Int. J. Pharm. 121 (1995) 95-105
13. Petkovska R., Cornett C., and Dimitrovska A. Development and validation of rapid resolution RP-HPLC method for simultaneous determination of atorvastatin and related compounds by use of chemometrics. Anal. Lett. 41 (2008) 992-1009
14. Kažoka H., and Madre M. Isocratic simultaneous normal-phase LC separation of four impurities for a stavudine synthesis control. Talanta 67 (2005) 98-102
15. Lin L.-Z., He X.-G., Lian L.-Z., King W., and Elliot J. Liquid chromatographic-electrospray mass spectrometric study of the phthalides of Angelica sinensis and chemical changes of Z-ligustilide. J. Chromatogr. A 810 (1998) 71-79
16. Brinker A.M., and Raskin I. Determination of triptolide in root extracts of Triptrygium wilfordii by solid-phase extraction and reverse-phase high-performance liquid chromatography. J. Chromatogr. A 1070 (2005) 65-70
17. Kong L., Li X., Zou H., Wang H., Mao X., Zhang Q., and Ni J. Analysis of terpene compounds in Cimicifuga foetida L. by reversed-phase high-performance liquid chromatography with evaporative light scattering detection. J. Chromatogr. A 936 (2001) 111-118
18. Seger C., Römpp H., Sturm S., Haslinger E., Schmidt P.C., and Hadacek F. Characterization of supercritical fluid extracts of St. John's Wort (Hypericum perforatum L.) by HPLC-MS and GC-MS. Eu. J. Pharm. Sci. 21 (2004) 453-463
19. Kursinszki L., Hank H., László I., and Szo{combining double acute accent}ke E. Simultaneous analysis of hyoscyamine, scopolamine, 6β-hydroxyhyoscyamine and apoatropine in Solanaceous hairy roots by reverse-phase high-performance liquid chromatography. J. Chromatogr. A 1091 (2005) 32-39
20. Ye M., Guo H., Guo H., and Guo D. Simultaneous determination of cytotoxic bufadienolides in the Chinese medicine ChanSu by high performance liquid chromatography coupled with photodiode-array and mass spectrometry detections. J. Chromatogr. B 838 (2006) 86-95
21. Pharmacopoeia of People's Republic of China vol. 1 (2005), Chemical Industry Press, Beijing pp. 118-119
22. Zhau Y., Li Z., Zhou X., Cai Z., Gong X., and Zhou C. Quality evaluation of Evodia rutaecarpa (Juss) Benth by high performance liquid chromatography with photodiode-array detection. J. Pharm. Biomed. Anal. 48 (2008) 1230-1236
23. Tappin M.R.R., Nakamura M.J., Siani A.C., and Lucchetti L. Development of a HPLC method for the determination of tetranortriterpenoids in Carpa guianensis seed oil by experimental design. J. Pharm. Biomed. Anal. 48 (2008) 1090-1095
24. Klick S. Evaluation of different injection techniques in the gas chromatographic determination of thermo labile trace impurities in a drug substance. J. Pharm. Biomed. Anal. 13 (1995) 563-566
25. Klick S. Evaluation of different injection techniques in the gas chromatographic determination of thermo labile trace impurities in a drug substance. J. Chromatogr. A 689 (1995) 69-76
26. Guo F.-Q., Liang Y.-Z., Xu C.-J., Li X.-N., and Huang L.-F. Determination of the volatile chemical constituents of Notoptergium incium by GC-MS and iterative or non-iterative chemometrics resolution methods. J. Chromatogr. A 1016 (2003) 99-110
27. Guo F.-Q., Liang Y.-Z., Xu C.-J., Li X.-N., and Huang L.-F. Analyzing of the volatile chemical constituents of Arteisi capillaries herba by GC-MS and correlative chemometric resolution methods. J. Pharm. Biomed. Anal. 35 (2004) 469-478
28. Li N., Deng C., Li Y., Ye H., and Zhang X. Gas chromatography-mass spectroscopy following microwave distillation and head space solid-phase microextraction for fast analysis of essential oil in dry traditional Chinese medicines. J. Chromatogr. A 1133 (2006) 29-34
29. Lao S.C., Li S.P., Kan K.K.W., Li P., Wan J.B., Wang Y.T., Dong T.T.X., and Tsim K.W.K. Identification and quantification of 13-components in Angelica sinensis (Danggui) by gas chromatography-mass spectroscopy coupled with pressurized liquid extraction. Anal. Chim. Acta 526 (2004) 131-137
30. Monforte-González M., Ayora-Talavera T., Maldonado-Mendoza I.E., and Loyola-Vargas V.M. Quantitative analysis of serpentine and ajmalicine in plant tissues of Catharanthus roseus and hyoscyamine and scopolamine in root tissues of Datura stramonium by thin layer chromatography-densitometry. Phytochem. Anal. 3 (1992) 117-121
31. Mroczek T., Glowniak K., and Kowalska J. Solid-liquid extraction and cation-exchange solid-phase extraction using a mixed mode polymeric sorbent of Datura and relate alkaloids. J. Chromatogr. A 1107 (2006) 9-18
32. Bempong D.K., Honigberg I.L., and Meltzer N.M. Separation of 13-cis and all-trans retinoic acid and their photo-degradation products using capillary zone electrophoresis and micellar electrokinetic chromatography (MEC). J. Pharm. Biomed. Anal. 11 (1993) 829-833
33. Mateus L., Cherkaoul S., Christen P., and Veuthey J.-L. Capillary electrophoresis-diode array detection-electrospray mass spectrometry for the analysis of selected tropane alkaloids in plant extracts. Electrophoresis 20 (1999) 3402-3409
34. Arráez-Román D., Zurek G., Bäβmann C., Seguro-Carretero A., and Fernández-Gutiérrez A. Characterization of Atropa belladonna L. compounds by capillary electrophoresis-electrospray ionization-time of flight-mass spectrometry and capillary electrophoresis-electrospray ionization-ion trap-mass spectrometry. Electrophoresis 29 (2008) 2112-2116
35. Mateus L., Cherkaoul S., Christen P., and Veuthey J.-L. The use of a Doehlert design in optimizing the analysis of selected tropane alkaloids by micellar electrokinetic capillary chromatography. J. Chromatogr. A 829 (1998) 317-325
36. Eeva M., Salo J.-K., and Oksman-Caldentey K.-M. Determination of the main tropane alkaloids from transformed Hyoscyamus muticus by capillary zone electrophoresis. J. Pharm. Biomed. Anal. 16 (1998) 717-722
37. Concept Paper on the Development of a Guideline on the Assessment of Genotoxic Constituents in Herbal Substances/Preparations. Committee for Medicinal Products (CHMP), European Medicines Agency, London, 25 October 2006 (EMEA/HPPC/413271/2006).
38. Bempong D.K., Honigberg I.L., and Meltzer N.M. Normal phase LC-MS determination of retinoic acid degradation products. J. Pharm. Biomed. Anal. 13 (1995) 285-291
39. Acebutolol Hydrochloride Monograph, Ph. Eur. Monograph 0871. European Pharmacopoeia, 6th edition as amended by supplements 6.1 and 6.2, 2009.
40. Atenolol Monograph, Ph. Eur. Monograph 0703. European Pharmacopoeia, 6th edition as amended by supplements 6.1 and 6.2, 2009.
41. Betamethasone Monograph, Ph. Eur. Monograph 0312. European Pharmacopoeia, 6th edition as amended by supplements 6.1 and 6.2, 2009.
42. Betamethasone Acetate Monograph, Ph. Eur. Monograph 0975. European Pharmacopoeia, 6th edition as amended by supplements 6.1 and 6.2, 2009.
43. Betaxolol Hydrochloride Monograph, Ph. Eur. Monograph 1072. European Pharmacopoeia, 6th edition as amended by supplements 6.1 and 6.2, 2009.
44. Carteolol Hydrochloride Monograph, Ph. Eur. Monograph 1972. European Pharmacopoeia, 6th edition as amended by supplements 6.1 and 6.2, 2009.
45. Celiprolol Hydrochloride Monograph, Ph. Eur. Monograph 1632. European Pharmacopoeia, 6th edition as amended by supplements 6.1 and 6.2, 2009.
46. Fluocinolone Acetonide Monograph, Ph. Eur. Monograph 0494. European Pharmacopoeia, 6th edition as amended by supplements 6.1 and 6.2, 2009.
47. Mometasone Furoate Monograph, Ph. Eur. Monograph 1449. European Pharmacopoeia, 6th edition as amended by supplements 6.1 and 6.2, 2009.
48. Mupirocin Monograph, Ph. Eur. Monograph 1450. European Pharmacopoeia, 6th edition as amended by supplements 6.1 and 6.2, 2009.
49. Propafenone Hydrochloride Monograph, Ph. Eur. Monograph 2103. European Pharmacopoeia, 6th edition as amended by supplements 6.1 and 6.2, 2009.
50. Stavudine Monograph, Ph. Eur. Monograph 2130. European Pharmacopoeia, 6th edition as amended by supplements 6.1 and 6.2, 2009.
51. Vincristine Sulfate Monograph, Ph. Eur. Monograph 0749. European Pharmacopoeia, 6th edition as amended by supplements 6.1 and 6.2, 2009.