Analysis of impurities and degradants in pharmaceuticals by high resolution tandem mass spectrometry and on-line H/D exchange LC/MS

American Pharmaceutical Review

Volumn 13, Issue 3, 2010, Pages 20-27

  Chen, Guodong ^a   Warrack, Bethanne M ^a   Goodenough, Angela K ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOTERICIN B; FLUCONAZOLE; ITRACONAZOLE; MOMETASONE FUROATE; POSACONAZOLE;

ARTICLE; DRUG DEGRADATION; DRUG IMPURITY; DRUG STRUCTURE; INTERNET; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; TANDEM MASS SPECTROMETRY;

EID: 77951994710     PISSN: 10998012     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (35)

1. Chen G, Pramanik BN, Liu YH, Mirza UA (2007): Applications of LC/MS in structural identifications of small molecules and proteins in drug discovery. Journal of Mass Spectrometry 42: 279-287. (Pubitemid 46426672)
2. Chen G, Zhang LK, Pramanik BN (2007). LC/MS: Theory, Instrumentation and Applications to Small Molecules, In: Kazakevich Y, LoBrutto R (eds.) HPLC for Pharmaceutical Scientists, Wiley, Inc., New York, pp 281-346.
3. Yamashita M, Fenn JB (1984): Electrospray ion source. Another variation on the free-jet theme. Journal of Physical Chemistry 88: 4451-4459.
4. Fenn JB, Mann M, Meng CK, Wong SF, Whitehouse CM (1989): Electrospray ionization for mass spectrometry of large biomolecules. Science 246: 64-71. (Pubitemid 19252085)
5. Horning EC, Horning MG, Carroll DI, Dzidic I, Stillwell RN (1973): New picogram detection system based on a mass spectrometer with an external ionization source at atmospheric pressure. Analytical Chemistry 45: 936-943.
6. Mamyrin BA, Karataev VI, Shmikk DV, Zagulin VA (1973): Mass reflectron. New nonmagnetic time-of-flight high-resolution mass spectrometer. Zhurnal Eksperimental'noi i Teoreticheskoi Fiziki 64: 82-89.
7. Guilhaus M (1995): Principles and instrumentation in time-of-flight mass spectrometry. Physical and instrumental concepts. Journal of Mass Spectrometry 30: 1519-1532.
8. Lawrence EO, Edlefsen NE (1930): Science 72:376.
9. Comisarow MB, Marshall AG (1974): Fourier transform ion cyclotron resonance spectroscopy. Chemical Physics Letters 25: 282-283.
10. Hardman M, Makarov AA (2003): Interfacing the orbitrap mass analyzer to an electrospray ion source. Analytical Chemistry 75: 1699-1705. (Pubitemid 36512611)
11. Hu Q, Noll RJ, Li H, Makarov A, Hardman M, Cooks RG: The orbitrap: a new mass spectrometer. Journal of Mass Spectrometry 40: 430-443.
12. Makarov A, Denisov E, Kholomeev A, Balschun W, Lange O, Strupat K, Horning S (2006): Performance evaluation of a hybrid linear ion trap/orbitrap mass spectrometer. Analytical Chemistry 78: 2113-2120.
13. Makarov A, Denisov E, Lange O, Horning S (2006): Dynamic range of mass accuracy in LTQ orbitrap hybrid mass spectrometer. Journal of the American Society for Mass Spectrometry 17: 977-982. (Pubitemid 43928612)
14. Cooks RG, Beynon JH, Caprioli RM, Lester GR. (1973). Metastable Ions, Elsevier, Amsterdam, The Netherlands.
15. McLafferty FW (1981): Tandem mass spectrometry. Science 214: 280-287.
16. Ohashi N, Furuuchi S, Yoshikawa M (1998): Usefulness of the hydrogen-deuterium exchange method in the study of drug metabolism using liquid chromatography-tandem mass spectrometry. Journal of Pharmaceutical and Biomedical Analysis 18: 325-334. (Pubitemid 28529437)
17. Olsen MA, Cummings PG, Kennedy-Gabb S, Wagner BM, Nicol GR, Munson B (2000): The use of deuterium oxide as a mobile phase for structural elucidation by HPLC/UV/ESI/MS. Analytical Chemistry 72: 5070-5078.
18. Liu DQ, Hop CE, Beconi MG, Mao A, Chiu SH (2001): Use of on-line hydrogen/ deuterium exchange to facilitate metabolite identification. Rapid Communication in Mass Spectrometry 15: 1832-1839. (Pubitemid 32927757)
19. Lam W, Ramanathan R (2002): In electrospray ionization source hydrogen/ deuterium exchange LC-MS and LC-MS/MS for characterization of metabolites. Journal of the American Society for Mass Spectrometry 13: 345-353.
20. Tolonen A, Turpeinen M, Uusitalo J, Pelkonen O (2005): A simple method for differentiation of monoisotopic drug metabolites with hydrogen-deuterium exchange liquid chromatography/electrospray mass spectrometry. European Journal of Pharmaceutical Science 25: 155-162. (Pubitemid 40602205)
21. Wolff JC, Laures AM (2006): 'On-the-fly' hydrogen/deuterium exchange liquid chromatography/mass spectrometry using a dual-sprayer atmospheric pressure ionisation source. Rapid Communication in Mass Spectrometry 20: 3769-3779.
22. Novak TJ, Helmy R, Santos I (2005): Liquid chromatography-mass spectrometry using the hydrogen/deuterium exchange reactions as a tool for impurity identification in pharmaceutical process development. Journal of Chromatography B 825: 161-168. (Pubitemid 41423599)
23. Liu DQ, Hop CECA (2005): Strategies for characterization of drug metabolites using liquid chromatography-tandem mass spectrometry in conjunction with chemical derivatization and on-Line H/D exchange approaches. Journal of Pharmaceutical and Biomedical Analysis 37: 1-18.
24. Chen G, Khusid A, Daaro I, Irish P, Pramanik BN (2007): Structural identification of trace level enol tautomer impurity by on-line hydrogen/deuterium exchange HRLC/ MS in a LTQ-Orbitrap hybrid mass spectrometer. Journal of Mass Spectrometry 42: 967-970. (Pubitemid 47057079)
25. Chen G, Daaro I, Pramanik BN, Piwinski JJ (2009): Structural characterization of in vitro rat liver microsomal metabolites of antihistamine desloratadine using LTQ-Orbitrap hybrid mass spectrometer in combination with online hydrogen/ deuterium exchange HR-LC/MS. Journal of Mass Spectrometry 44: 203-213.
26. Pramanik BN, Bartner PL, Chen G (1999): The role of mass spectrometry in the drug discovery process. Current Opinion in Drug Discovery & Development 2: 401-417. (Pubitemid 29372365)
27. Chen G, Daaro I, Pramanik BN (2007): Structural identifications of mometasone furoate steroid related impurities in a LTQ-Orbitrap hybrid mass spectrometer. Proceedings of the 55th ASMS Conference on Mass Spectrometry and Allied Topics, Abstract # A074176, Indianapolis, Indiana, June 3-7.
28. Nomeir AA, Pramanik BN, Heimark L, Bennett F, Veals J, Bartner P, Hilbert M, Saksena A, McNamara P, Girijavallabhan V, Ganguly AK, Lovey R, Pike R, Wang H, Liu YT, Kumari P, Korfmacher W, Lin CC, Cacciapuoti A, Loebenberg D, Hare R, Miller G, Pickett C (2008): Posaconazole (Noxafil, SCH 56592), a new azole antifungal drug, was a discovery based on the isolation and mass spectral characterization of a circulating metabolite of an earlier lead (SCH 51048). Journal of Mass Spectrometry 43: 509-517.
29. Perfect JR, Cox GM, Dodge RK, Schell WA (1996): In vitro and in vivo efficacies of the azole SCH56592 against Cryptococcus neoformans. Antimicrobial Agents and Chemotherapy 40: 1910-1913.
30. Galgiani JN, Lewis ML.In vitro studies of activities of the antifungal triazoles SCH56592 and itraconazole against Candida albicans, Cryptococcus neoformans, and other pathogenic yeasts (1997): Antimicrobial Agents and Chemotherapy 41: 180-183.
31. Graybill JR, Bocanegra R, Najvar LK, Luther MF, Loebenberg D (1998): SCH56592 treatment of murine invasive aspergillosis. Journal of Antimicrobial Chemotherapy 42: 539-542 (Pubitemid 28473018)
32. Uchida K, Yokota N, Yamaguchi H (2001): In vitro antifungal activity of posaconazole against various pathogenic fungi. International Journal of Antimicrobial Agents 18: 167-172.
33. Frampton JE, Scott LJ (2008): Posaconazole: a review of its use in the prophylaxis of invasive fungal infections. Drugs 68: 993-1016. (Pubitemid 351652926)
34. Feng W, Liu H, Chen G, Malchow R, Bennett F, Lin E, Pramanik B, Chan TM (2001): Structural characterization of the oxidative degradation products of an antifungal agent SCH 56592 by LC-NMR and LC-MS. Journal of Pharmaceutical and Biomedical Analysis 25: 545-557. (Pubitemid 32496272)
35. Daaro I, Chen G, Schwartzburg I, Pramanik BN (2009): Characterization of Degradation Products of A Triazole Antifungal Agent by HR-LC/MS/MS and On-Line H/D Exchange LC/MS in LTQ-Orbitrap Mass Spectrometer. Proceedings of the 57th ASMS Conference on Mass Spectrometry and Allied Topics, Abstract # A090128, Philadelphia, PA, May 31 - June 4, 2009