Quantitation of a polymorphic mixture of an active pharmaceutical ingredient with solid state 13C CPMAS NMR spectroscopy

International Journal of Pharmaceutics

Volumn 394, Issue 1-2, 2010, Pages 18-25

  Virtanen, Tommi ^a   Maunu, Sirkka L ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

DECRA; Polymorphism; Quantitation; Solid state NMR

Indexed keywords

2 [4 [4 METHYL 6 OXO 4,5 DIHYDRO 1H PYRIDAZIN 3 YL]HYDRAZINYLIDENE]PROPANEDINITRILE; CAS 141505 33 1; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG; 2-((4-(4-METHYL-6-OXO-4,5-DIHYDRO-1H-PYRIDAZIN-3-YL)PHENYL)HYDRAZINYLIDENE)PROPANEDINITRILE; HYDRAZONE DERIVATIVE;

ACCURACY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMOMETRIC ANALYSIS; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DRUG MANUFACTURE; DRUG MIXTURE; DRUG STRUCTURE; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; SOLID STATE; STRUCTURE ANALYSIS; ALGORITHM; CHEMISTRY; CRYSTALLIZATION; MEDICINAL CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHARMACEUTICS; PROCEDURES;

ALGORITHMS; CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; HYDRAZONES; MAGNETIC RESONANCE SPECTROSCOPY; PYRIDAZINES; TECHNOLOGY, PHARMACEUTICAL;

EID: 77953717797     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2010.04.017     Document Type: Article

References (31)

1. Agatonovic-Kustrin S., Rades T., Wu V., Saville D., Tucker I. Determination of polymorphic forms of ranitide-HCl by DRIFTS and XRPD. J. Pharm. Biomed. Anal. 2001, 25:741-750.
2. Brittain H.G., Bogdanowich S.J., Bugay D.E., DeVincentis J., Lewen G., Newman A.W. Physical characterization of pharmaceutical solids. Pharm. Res. 1991, 8:963-973.
3. Bugay D.E. Characterization of the solid-state: spectroscopic techniques. Adv. Drug Deliv. Rev. 2001, 48:43-65.
4. Gamberini M., Baraldi C., Tinti A., Rustichelli C., Ferioli V., Gamberini G. Solid state characterizaton of chloramphenicol palmitate. Raman spectroscopy applied to pharmaceutical polymorphs. J. Mol. Struct. 2006, 785:216-224.
5. 13C CP/MAS NMR. Pharm. Res. 1996, 13:1095-1104.
6. Gervais C., Profeta M., Lafond V., Bonhomme C., Azaïs T., Mutin H., Pickard C.J., Mauri F., Babonneau F. Combined ab initio computational and experimental multinuclear solid-state magnetic resonance study of phenylphosphonic acid. Magn. Reson. Chem. 2004, 42:445-452.
7. Gustafsson C., Lennholm H., Iversen T., Nyström C. Comparison of solid-state NMR and isothermal microcalorimetry in the assessment of the amorphous component of lactose. Int. J. Pharm. 1998, 174:243-252.
8. Harris R.K. Quantitative aspects of high-resolution solid-state nuclear magnetic resonance spectroscopy. Analyst 1985, 110:649-655.
9. Harris R.K. NMR studies of organic polymorphs & solvates. Analyst 2006, 131:351-373.
10. Harris R.K., Hodgkinson P., Larsson T., Muruganantham A. Quantification of bambuterol hydrochloride in a formulated product using solid-state NMR. J. Pharm. Biomed. Anal. 2005, 38:858-864.
11. 14N. J. Magn. Reson. 2002, 159:25-35.
12. 2. Pharm. Res. 2001, 18:682-688.
13. 13C NMR spectroscopy. Spectrochim. Acta Part A 1999, 55:2877-2882.
14. McMahon L.E., Timmins P., Williams A.C., York P. Characterization of dihydrates prepared from carbamazepine polymorphs. J. Pharm. Sci. 1996, 85:1064-1069.
15. Mooibroek S., Wasylishen R.E. A carbon-13 nuclear magnetic resonance study of solid tetracyclines. Can. J. Chem. 1987, 65:357-362.
16. Offerdahl T.J. Solid-state nuclear magnetic resonance spectroscopy for analyzing polymorphic drug forms and formulations. Pharm. Technol. 2006, 24-42.
17. Opella S., Frey M., Cross T. Detection of individual carbon resonances in solid proteins. J. Am. Chem. Soc. 1979, 101:5856-5857.
18. 13C NMR spectroscopy and powder X-ray diffraction for analyzing mixtures of polymorphs of neotame. Anal. Chem. 1999, 71:3325-3331.
19. Patel A.D., Luner P.E., Kemper M.S. Quantitative analysis of polymoprhs in binary and multi-component powder mixtures by near-infrared reflectance spectroscopy. Int. J. Pharm. 2000, 206:63-74.
20. Raghavan K., Dwivedi A., Campbell G.C., Johnston E., Levorse D., McCauley J., Hussain M. A spectroscopic investigation of losartan polymorphs. Pharm. Res. 1993, 10:900-904.
21. Reutzel-Edens S.M., Kleemann R.L., Lewellen P.L., Borghese A.L., Antoine L.J. Crystal forms of LY334370 HCl: isolation, solid-state characterization, and physicochemical properties. J. Pharm. Sci. 2003, 92:1196-1205.
22. Roberts S.N.C., Williams A.C., Grimsey I.M., Booth S.W. Quantitative analysis of mannitol polymorphs. X-ray powder diffractometry-exploring preferred orientation effects. J. Pharm. Biomed. Anal. 2002, 28:1149-1159.
23. Sheikhzadeh M., Rohani S., Jutan A., Manifar T., Murthy K., Horne S. Solid-state characterization of buspirone hydrochloride polymorphs. Pharm. Res. 2006, 23:1043-1050.
24. Smith J.R., Xu W., Raftery D. Analysis of conformational polymorphism in pharmaceutical solids using solid-state NMR and electronic structure calculations. J. Phys. Chem. B 2006, 110:7766-7776.
25. Stephenson G.A., Forbes R.A., Reutzel-Edens S.M. Characterization of the solid state: quantitative issues. Adv. Drug Deliv. Rev. 2001, 48:67-90.
26. Tozuka Y., Ito A., Seki H., Oguchi T., Yamamoto K. Characterization and quantitation of clarithromycin polymorphs by powder X-ray diffractometry and solid-state NMR spectroscopy. Chem. Pharm. Bull. 2002, 50:1128-1130.
27. Windig W., Antalek B. Direct exponential curve resolution algorithm (DECRA): a novel application of the generalized rank annihilation method for a single spectral mixture data set with exponentially decaying contribution profiles. Chemom. Intell. Lab. Syst. 1997, 37:241-254.
28. Wolfram Research, Inc., 2003. Mathematica, version 5.0. Wolfram Research, Inc., Champaign, Illinois.
29. Yates J.R., Dobbins S.E., Pickard C.J., Mauri F., Ghi P.Y., Harris R.K. A combined first principles computational and solid-state NMR study of a molecular crystal: flurbiprofen. Phys. Chem. Chem. Phys. 2005, 7:1402-1407.
30. Zell M.T., Padden B.E., Grant D.J.W., Schroeder S.A., Wachholder K.L., Prakash I., Munson E.J. Investigation of polymorphism in aspartame and neotame using solid-state NMR spectroscopy. Tetrahedron 2000, 56:6603-6616.
31. 13C CP/MAS NMR spectroscopy and direct exponential curve resolution algorithm. J. Am. Chem. Soc. 1999, 121:11554-11557.