Characterization of the solid state: Quantitative issues

Advanced Drug Delivery Reviews

Volumn 48, Issue 1, 2001, Pages 67-90

  Stephenson, Gregory A ^a   Forbes, Robert A ^a   Reutzel Edens, Susan M ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

Crystallinity; IR; Near IR; NMR; Raman; Solid state; Spectroscopy; X ray powder diffraction

Indexed keywords

SAFETY TESTING; SOLID STATE PHYSICS;

QUANTITATIVE PHASE ANALYSES;

DRUG PRODUCTS;

CEFAZOLIN; CEFEPIME; CROMOGLYCATE DISODIUM; DELAVIRDINE; LORACARBEF; PENICILLIN G;

ACCURACY; ARTICLE; CRYSTALLIZATION; DRUG DOSAGE FORM; DRUG FORMULATION; INFRARED SPECTROSCOPY; INTERMETHOD COMPARISON; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; QUANTITATIVE ASSAY; RAMAN SPECTROMETRY; SOLID STATE; X RAY POWDER DIFFRACTION;

CHEMISTRY, PHARMACEUTICAL; CRYSTALLOGRAPHY; PHARMACEUTICAL PREPARATIONS; SPECTROPHOTOMETRY;

EID: 0035897595     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0169-409X(01)00099-0     Document Type: Article

References (80)

1. Haleblian J.K., McCrone W.J. Pharmaceutical applications of polymorphism. J. Pharm. Sci. 58:1969;911-929.
2. Byrn S., Pfeiffer R., Ganey M., Hoiberg C., Poochikian G. Pharmaceutical solids: a strategic approach to regulatory considerations. Pharm. Res. 12:1995;945-954.
3. Yu L., Reutzel S.M., Stephenson G.A. Physical characterization of polymorphic drugs: an integrated characterization strategy. Pharm. Sci. Tech. Today. 1:1998;118-127.
4. Alexander L., Klug H.P. Basic aspects of X-ray absorption in quantitative diffraction analysis of powder mixtures. Anal. Chem. 20:1948;886-889.
5. Christ C.L., Barnes R.B., Williams E.F. Organic quantitative analysis using the Geiger counter X-ray spectrometer. Anal. Chem. 20:(9):1948;789-795.
6. J.W. Shell, X-ray and Crystallographic Applications in Pharmaceutical Research II. J. Pharm. Sci. (1963) 24-29.
7. Smith D.K., Johnson G.G. Jr., Scheible A., Wims A.M., Johnson J.L., Ullmann G. Quantitative X-ray powder diffraction method using the full diffraction pattern. Powder Diffr. 2:(2):1987;73-77.
8. Thomas E.V. A primer on multivariate calibration. Anal. Chem. 66:(15):1994;795A-804A.
9. S.R Maple, E.G. Groleau, G.A. Stephenson, Quantitative Analysis of Polymorphism Using Principle Component and Partial Least Squares Methods, Personal Communication.
10. Young R.A. The Rietveld Method. 1995;Oxford University Press Inc, New York.
11. Toraya H., Tsusaka S. Quantitative phase analysis using the whole-powder-pattern decomposition method. I. Solution from knowledge of chemical compositions. J. Appl. Cryst. 28:1995;392-399.
12. Dollase W.A. Correction of intensities for preferred orientation in powder diffractometry: application of the March model. J. Appl. Cryst. 19:1986;267-272.
13. Brittain H.G. Spectral methods for the characterization of polymorphs and solvates. J. Pharm. Sci. 86:1997;405-412.
14. Fuller M.P., Griffiths P.R. Diffuse reflectance measurements by infrared Fourier transform spectrometry. Anal. Chem. 50:1978;1906-1910.
15. Yang S.S., Guillory J.K. Polymorphism of sulfonamides. J. Pharm. Sci. 61:1972;626-640.
16. Kubelka P., Munk F. Ein beitung sur optik der farbanstriche. Z. Tech. Phys. 12:1931;593-601.
17. Bugay D.E., Newman A.W., Findlay W.P. Quantification of cefepime 2HCl dihydrate in cefepime 2HCl monohydrate by diffuse reflectance IR and powder X-ray diffraction techniques. J. Pharm. Biomed. Anal. 15:1996;49-61.
18. Roston D.A., Walters M.C., Rhinebarger R.R., Ferro L.J. Characterization of polymorphs of a new anti-inflammatory drug. J. Pharm. Biomed. Anal. 11:1993;293-300.
19. Eustaquio A., Graham P., Jee R.D., Moffatt A.C., Trafford A.D. Quantification of paracetamol in intact tablets using near-infrared transmittance spectroscopy. Analyst. 123:1998;2303-2306.
20. Berntsson O., Burger T., Folestad S., Danielsson L.G., Kuhn J., Fricke J. Effective sample size in diffuse reflectance near-IR spectrometry. Anal. Chem. 71:(3):1999;617-623.
21. Blanco M., Coello J., Iturriaga H., Maspoch S., de la Pezuela C. Effect of data prepocessing methods in near-infrared diffuse reflectance spectroscopy for the determination of the active compound in a pharmaceutical preparation. Appl. Spectrosc. 51:(2):1997;240-246.
22. Martens H., Naes T. Multivariate Calibration. 1989;John Wiley and Sons, New York. Chapter 5.
23. General Information Chapter 〈1119〉 Near-Infrared Spectrophotometry, Pharmacopeial Forum 24 (4) (1998) 6463-6473.
24. Zhou X., Hines P., Borer M.W. Moisture determination in hygroscopic drug substances by near infrared spectroscopy. J. Pharm. Biomed. Anal. 17:1998;219-225.
25. A.J. O'Neil, R.D. Jee, A.C. Moffat, The application of multiple linear regression to the measurement of the median particle size of drugs and pharmaceutical excipients by near-infrared spectroscopy, 123 (1998) 2297-2302.
26. Findlay W.P., Bugay D.E. Utilization of Fourier transform-Raman spectroscopy for the study for pharmaceutical crystal forms. J. Pharm. Biomed. Anal. 16:1998;921-930.
27. Langkilde F.W., Sjoblom J., Tekenbers-Hjelte L., Mrak J. Quantitative FT-Raman analysis of two crystal forms of a pharmaceutical compound. J. Pharm. Biomed. Anal. 13:1997;687-696.
28. Burum D.P. Combined Rotation and Multiple Pulse Spectroscopy (CRAMPS). Concepts Magn. Reson. 2:1990;213-227.
29. Jackson P., Harris R.K. A practical guide to combined rotation and multiple pulse NMR spectroscopy of solids. Magn. Res. Chem. 26:1988;1003-1011.
30. Hays G.R. High resolution carbon-13 solid-state nuclear magnetic resonance spectroscopy. Analyst. 107:1982;241-252.
31. Harris R.K. Quantitative aspects of high-resolution solid-state nuclear magnetic resonance spectroscopy. Analyst. 110:1985;649-655.
32. Andrew E.R. Magic angle spinning. Int. Rev. Phys. Chem. 1:1981;195-224.
33. Frye J.S., Maciel G.E. Setting the magic angle using a quadrupolar nuclide. J. Magn. Reson. 48:1982;125-131.
34. Dixon W.T. Spinning-sideband-free and spinning-sideband-only NMR spectra in spinning samples. J. Chem. Phys. 77:(4):1982;1800-1809.
35. Frye J.S. Comparison of inversion recovery methods for measuring longitudinal relaxation rates. Concepts Magn. Reson. 1:1989;27-33.
36. Pines A., Gibby M.G., Waugh J.S. Proton-enhanced NMR of dilute spins in solids. J. Chem. Phys. 59:1973;569-590.
37. Alemany L.B., Grant D.M., Pugmire R.J., Alger T.D., Zilm K.W. Cross polarization and magic angle sample spinning NMR spectra of model organic compounds. 1. Highly protonated molecules. J. Am. Chem. Soc. 105:1983;2133-2141.
38. Alemany L.B., Grant D.M., Pugmire R.J., Alger T.D., Zilm K.W. Cross polarization and magic angle sample spinning NMR spectra of model organic compounds. 2. Molecules of low or remote protonation. J. Am. Chem. Soc. 105:1983;2142-2147.
39. Mehring M. Principles of High Resolution in Solids. 1983;Springer-Verlag, Berlin. Chapter 4.
40. Zumbulyadis N. Selective carbon excitation and the detection of spatial heterogeneity in cross-polarization magic-angle-spinning NMR. J. Magn. Reson. 59:1983;486-494.
41. Havens J.R., Koenig J.L. Applications of high-resolution carbon-13 nuclear magnetic resonance spectroscopy to solid polymers. Appl. Spectrosc. 37:1983;226-249.
42. Lindberg J.J., Hortling B. Cross polarization-magic angle spinning NMR studies of carbohydrates and aromatic polymers. Adv. Polym. Sci. 66:1985;1-22.
43. 13C in solids using CPMAS-DD-NMR spectroscopy. Anal. Chim. Acta. 283:1993;1033-1043.
44. 13C cross polarization NMR spectroscopy. Computers Chem. 17:1993;73-79.
45. Duddu S.P., Khin-Khin A., Grant D.J.W., Suryanarayanan R. A novel X-ray powder diffraction method for studying the reaction between pseudoephedrine enantiomers. J. Pharm. Sci. 86:(3):1997;340-345.
46. Suryanarayanan R. Determination of the relative amounts of anhydrous carbamazepine and carbamazepine dihydrate in a mixture by powder X-ray diffraction. Pharm. Res. 6:(12):1989;1017-1024.
47. Suryanarayanan R., Herman C.S. Quantitative analysis of the active tablet ingredient by powder X-ray diffraction. Pharm. Res. 8:(3):1991;393-399.
48. Deeley C.M., Spragg R.A., Threlfall T.L. A comparison of Fourier transform infrared and near infrared Fourier transform Raman spectroscopy for quantitative measurements: an application in polymorphism. Spectrochim. Acta. 47A:(9-10):1991;1217-1223.
49. Miyazaki S., Nakano M., Arita T. Polymorphic transformation of chlortetracycline hydrochloride crystals studied by infrared spectrophotometric method. Chem. Bull. Pharm. 24:1976;1832-1838.
50. Higuchi W.I., Hamlin W.E., Mehta S.C. Infrared attenuated total reflectance (ATR) method for observing the water-mediated surface phase reversion of methylprednisolone II to I during dissolution. J. Pharm. Sci. 58:1969;1145-1146.
51. Kang I.P.S., Kendall C.E., Lee R.W. Infrared spectroscopy using attenuated total reflection. J. Pharm. Pharmacol. 26:1974;201-204.
52. Hartauer K.J., Guillory J.K. Quantitative Fourier transform-infrared/attenuated total reflectance (FT-IR/ATR) analysis of trimethoprim and sulfamethoxazole in a pharmaceutical formulation using partial least squares. Pharm. Res. 6:1989;608-611.
53. Salari A., Young R.E. Application of attenuated total reflectance FTIR spectroscopy to the analysis of mixtures of pharmaceutical polymorphs. Int. J. Pharm. 163:1998;157-166.
54. Hartauer K.J., Miller E.S., Guillory J.K. Diffuse reflectance infrared Fourier transform spectroscopy for the quantitative analysis of mixtures of polymorphs. Int. J. Pharm. 85:1992;163-174.
55. Tudor A.M., Church S.J., Hendra P.J., Lee D.G., Melia C.D., Mitchell R.C., Davies M.C. The application of near-infrared Fourier transform Raman spectroscopy to the analysis of polymorphic forms of cimetidine. Spectrochim. Acta. 47A:1991;1389-1393.
56. Tudor A.M., Church S.J., Hendra P.J., Davies M.C., Melia C.D. The qualitative and quantitative analysis of chlorpropamide polymorphic mixtures by near-infrared Fourier transform Raman spectroscopy. Pharm. Res. 10:1993;1772-1776.
57. Jalsovsky G., Egyed O., Holly S., Hegedus B. Investigation of the morphological composition of cimetidine by FT-Raman spectroscopy. Appl. Spectrosc. 49:(8):1995;1142-1145.
58. Forbes R.A., McGarvey B.M., Smith D.R. Measurement of residual isopropyl alcohol in loracarbef by near-infrared reflectance spectroscopy. Anal. Chem. 71:(6):1999;1232-1239.
59. Dreassi E., Ceramellin G., Corti P., Lonardi S., Perrucccio P.L. Near-infrared reflectance spectroscopy in the determination of the physical state of primary materials in pharmaceutical production. Analyst. 120:1995;1005-1008.
60. Norris T., Aldridge P.K., Sekulic S.S. Determination of end-points for polymorph conversions of crystalline organic compounds using on-line near-infrared spectroscopy. Analyst. 122:1997;549-552.
61. 13C-NMR spectroscopy of polymers. Angew. Chem., Int. Ed. Engl. 27:1988;1468-1483.
62. Byrn S.R., Pfeiffer R.R., Stephenson G., Grant D.J.W., Gleason W.B. Solid-state pharmaceutical chemistry. Chem. Mater. 6:1994;1148-1158.
63. Saindon P.J., Cauchon N.S., Sutton P.A., Chang C.-J., Peck G.E., Byrn S.R. Solid-state nuclear magnetic resonance (NMR) spectra of pharmaceutical dosage forms. Pharm. Res. 10:1993;197-203.
64. Threlfall T.L. Analysis of organic polymorphs: a review. Analyst. 120:1995;2435-2460.
65. Fletton R.A., Harris R.K., Kenwright A.M., Lancaster R.W., Packer K.J., Sheppard N. A comparative spectroscopic investigation of three pseudopolymorphs of testosterone using solid-state i.r. and high-resolution solid-state NMR. Spectrochim. Acta. 43A:1987;1111-1120.
66. Bugay D.E. Solid-state nuclear magnetic resonance spectroscopy: theory and pharmaceutical applications. Pharm. Res. 10:(3):1993;317-327.
67. 31P MAS NMR of organophosphorus compounds. Magn. Reson. Chem. 28:1990;S47-51.
68. Harris R.K., Kenwright A.M., Say B.J., Yeung R.R., Fletton R.A., Lancaster R.W., Hardgrove G.L. Jr. Cross-polarization/magic-angle spinning NMR studies of polymorphism: cortisone acetate. Spectrochim. Acta. 46A:1990;927-935.
69. Stockton G.W., Godfrey R., Hitchcock P., Mendelsohn R., Mowery P.C., Walker A.F. Crystal polymorphism in pendimethalin herbicide is driven by electronic delocalization and changes in intramolecular hydrogen bonding. A crystallographic, spectroscopic, and computational study. J. Chem. Soc. Perkin Trans. II:1998;2061-2071.
70. 13C CP/MAS NMR. Pharm. Res. 13:1996;1095-1104.
71. 2O) in a mixture by solid-state nuclear magnetic resonance (NMR). Pharm. Res. 7:1990;184-187.
72. 13C CP/MAS NMR study. J. Am. Chem. Soc. 107:1985;7040-7044.
73. Suryanaraynan R., Mitchell A.G. Evaluation of two concepts of crystallinity using calcium gluceptate as a model compound. Int. J. Pharm. 24:1985;1-17.
74. Takahashi Y., Nakashima K., Nakagawa H., Sugimoto I. Effects of grinding and drying on the solid-state stability of ampicillin trihydrate. Chem. Pharm. Bull. 32:(12):1984;4963-4970.
75. Kaneniwa N., Otsuka M. Effect of grinding on the transformation of polymorphs of chloramphenicol palmitate. Chem. Pharm. Bull. 33:(4):1985;1660-1668.
76. L.S. Crocker, J.A. McCauley, Comparison of the crystallinity of imipenem samples by X-ray diffraction of amorphous material, 84(2) (1995) 226-227.
77. Otsuka M., Kaneniwa N. A kinetic study of the crystallization of non-crystalline indomethacin under isothermal conditions. Chem. Pharm. Bull. 36:(10):1988;4026-4032.
78. Taylor L.S., Zografi G. The quantitative analysis of crystallinity using FT-Raman spectroscopy. Pharm. Res. 15:(5):1998;755-761.
79. Kamat M.S., Osawa T., DeAngelis R.J., Koyama Y., DeLuca P.P. Estimation of the degree of crystallinity of cefazolin sodium by X-ray and infrared methods. Pharm. Res. 5:(7):1988;426-429.
80. Le Botlan D., Casseron F., Lantier F. Polymorphism of sugars studied by time-domain NMR. Analysis. 26:1998;198-204.