Detection, identification and quantification of a new de-fluorinated impurity in casopitant mesylate drug substance during late phase development: An analytical challenge involving a multidisciplinary approach

Journal of Pharmaceutical and Biomedical Analysis

Volumn 54, Issue 1, 2011, Pages 67-73

  Turco, Lucilla ^a   Provera, Stefano ^a,b   Curcuruto, Ornella ^a,b   Bernabè, Elena ^a,c   Nicoletti, Anna ^a,c   Martini, Luca ^a,b   Castoldi, Damiano ^a,b   Cimarosti, Zadeo ^a,b   Papini, Damiano ^a,b   Marchioro, Carla ^a,b   Dams, Riet ^a,b  

^a GSK   (Italy)

^b Aptuit Inc   (United States)

^c INFINEUM UK LTD   (United Kingdom)

Author keywords

Casopitant mesylate; LC MS; NMR spectroscopy; Orthogonal analytical control

Indexed keywords

CASOPITANT; FLUORINE;

ACCURACY; ARTICLE; DEFLUORINATION; DRUG DETERMINATION; DRUG IDENTIFICATION; DRUG PURITY; FLUORINE NUCLEAR MAGNETIC RESONANCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS;

CHEMISTRY TECHNIQUES, ANALYTICAL; CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, LIQUID; DRUG CONTAMINATION; FLUORINE; HALOGENATION; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, CHEMICAL; PHARMACEUTICAL PREPARATIONS; PIPERAZINES; PIPERIDINES; QUALITY CONTROL; REPRODUCIBILITY OF RESULTS;

EID: 77957018854     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2010.08.010     Document Type: Article

References (13)

1. Di Fabio R., Griffante C., Alvaro G., Pentassuglia G., Pizzi D.A., Donati D., Rossi T., Guercio G., Mattioli M., Cimarosti Z., Marchioro C., Provera S., Zonzini L., Montanari D., Melotto S., Gerrard P.A., Trist D.G., Ratti E., Corsi M. Discovery process and pharmacological characterization of 2-(S)-(4-fluoro-2-methylphenyl)piperazine-1-carboxylic acid [1-(R)-(3,5-bis-trifluoromethylphenyl)ethyl]methylamide (Vestipitant) as a potent, selective, and orally active NK1 receptor antagonist. J. Med. Chem. 2009, 52:3238-3247.
2. Qiu F., Norwood D.L. Identification of pharmaceutical impurities. J. Liq. Chromatogr. R. T. 2007, 30:877-935.
3. Alsante K.M., Hatajik T.D., Lohr L.L., Sharp T.R. Isolation and identification of process related impurities and degradation products from pharmaceutical drug candidates, part I. Am. Pharm. Rev. 2001, 4:70-78.
4. Lohr L.L., Sharp T.R., Alsante K.M., Hatajik T.D. Isolation and identification of process related impurities and degradation products from pharmaceutical drug candidates: part II-the roles of NMR and mass spectrometry. Am. Pharm. Rev. 2001, 104-113.
5. Bartos D., Görög S. Recent advances in the impurity profiling of drugs. Curr. Pharm. Anal. 2008, 4:215-230.
6. Vasanti S., Sulabha S. Impurity profile-a review. Drug Invention Today 2009, 1:81-88.
7. Q3A (R2) Impurities in new drug substances. ICH Harmonized Tripartite Guideline 2006.
8. Evilia R.F. Quantitative NMR spectroscopy. Anal. Lett. 2001, 34:2227-2236.
9. 31P NMR spectroscopy. Applications to analytical standards and agricultural chemicals. Anal. Chem. 1998, 70:4921-4928.
10. Argentine M.D., Owens P.K., Olsen B.A. Strategies for the investigation and control of process-related impurities in drug substances. Adv. Drug Deliv. Rev. 2007, 59:12-28.
11. Dams R., Bernabe E., Nicoletti A., Loda C., Martini L., Papini D. Quantitation of a de-fluorinated analogue of casopitant mesylate by normal phase liquid chromatography-mass spectrometry. Rapid Commun. Mass Spectrom. 2010, 10.1002/rcm.4688.
12. Cimarosti Z., Bravo F., Castoldi D., Tinazzi F., Provera S., Perboni A., Westerduin P. Application of the QbD principles in the development of the Casopitant Mesylate manufacturing process. Process research studies for the definition of the control strategy for Stages 2a, 2b and 2c. Org. Process Res. Dev. 2010, 14:805-814.
13. Bravo F., Cimarosti Z., Tinazzi F., Castoldi D., Stonestreet P., Galgano A., Westerduin P. Development of a control strategy for the control of the manufacturing process of a de-fluorinated analogue of Casopitant Mesylate following the quality by design principles. Org. Process Res. Dev. 2010, 14:832-839.