Qualitative in situ analysis of multiple solid-state forms using spectroscopy and partial least squares discriminant modeling

Journal of Pharmaceutical Sciences

Volumn 96, Issue 7, 2007, Pages 1802-1820

  Kogermann, Karin ^a,b   Aaltonen, Jaakko ^a   Strachan, Clare J ^a   Pöllänen, Kati ^c   Veski, Peep ^b   Heinämäki, Jyrki ^a   Yliruusi, Jouko ^a   Rantanen, Jukka ^a,d  

^a UNIVERSITY OF HELSINKI   (Finland)

^b UNIVERSITY OF TARTU   (Estonia)

^c LAPPEENRANTA UNIVERSITY OF TECHNOLOGY   (Finland)

^d UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Carbamazepine; Dehydration; Hydrate; Multivariate analysis; Near infrared spectroscopy; Partial least squares discriminant analysis; Piroxicam; Raman spectroscopy; Solid state; Transition

Indexed keywords

CARBAMAZEPINE; CARBAMAZEPINE DIHYDRATE; PIROXICAM; PIROXICAM DIHYDRATE; UNCLASSIFIED DRUG;

ARTICLE; DEHYDRATION; DIFFERENTIAL SCANNING CALORIMETRY; DISCRIMINANT ANALYSIS; INTERMETHOD COMPARISON; NEAR INFRARED SPECTROSCOPY; PARTIAL LEAST SQUARES REGRESSION; PHASE TRANSITION; QUALITATIVE ANALYSIS; RAMAN SPECTROMETRY; SOLID STATE; SPECTROSCOPY; THERMOGRAVIMETRY; TITRIMETRY; X RAY DIFFRACTION;

EID: 34547182895     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.20840     Document Type: Article

References (49)

1. Bernstein J. 2002. Polymorphism in molecular crystals. Oxford: Oxford Science Publications.
2. Khankari RK, Grant DJW. 1995. Pharmaceutical hydrates. Thermochim Acta 248:61-79.
3. Morris KR, Griesser UJ, Eckhardt CJ, Stowell JG. 2001. Theoretical approaches to physical transformations of active pharmaceutical ingredients during manufacturing processes. Adv Drug Deliv Rev 48:91-114.
4. Zhang GZZ, Law D, Schmitt EA, Qiu Y. 2004. Phase transformation considerations during process development and manufacture of solid oral dosage forms. Adv Drug Deliv Rev 56:371-390.
5. Ahlqvist MUA, Taylor LS. 2002. Water dynamics in channel hydrates investigated using H/D exchange. Int J Pharm 241:253-261.
6. FDA. 2004. U.S. Food and Drug Administration. Guidance for Industry: PAT - A Framework for Innovative Pharmaceutical Development, Manufacturing and Quality Assurance. US Food and Drug Administration, ed., Rockville, MD.
7. Blanco M, Coello HI, Maspoch S, Pou N. 2001. Influence of the procedure used to prepare the calibration sample set on the performance of near infrared spectroscopy in quantitative pharmaceutical analyses. Analyst 126:1129-1134.
8. Taylor LS, Langkilde FW. 2000. Evaluation of solid-state forms present in tablets by Raman spectroscopy. J Pharm Sci 89:1342-1353.
9. Wang F, Wachter JA, Antosz FJ, Berglund KA. 2000. An investigation of solvent-mediated polymorphic transformation of progesterone using in situ Raman spectroscopy. Org Process Res Dev 4:391-395.
10. Svensson O, Josefson M, Langkilde FW. 2000. The synthesis of metoprolol monitored using Raman spectroscopy and chemometrics. Eur J Pharm Sci 11:141-155.
11. Jorgensen AC, Miroshnyk I, Karjalainen M, Jouppila K, Siiriä S, Antikainen O, Rantanen J. 2006. Multivariate data analysis as a fast tool in evaluation of solid state phenomena. J Pharm Sci 95:906-916.
12. McCreery RL. 2000. Raman spectroscopy for chemical analysis. New York: Wiley-Interscience, A John Wiley and Sons, Inc., Publication.
13. Krishnan RS, Shankar RK. 1981. Raman effect: History of the discovery. J Raman Spectrosc 10:1-8.
14. O'Brien LE, Timmins P, Williams AC, York P. 2004. Use of in situ FT-Raman spectroscopy to study the kinetics of the transformation of carbamazepine polymorphs. J Pharm Biomed Anal 36:335-340.
15. Byrn SR, Pfeiffer R, Ganey M, Hoiberg C, Poochikian G. 1995. Pharmaceutical solids: A strategic approach to regulatory considerations. Pharm Res 12:945-954.
16. Martindale W. 1993. Martindale. The extra pharmacopoeia, 30th ed. London: The Pharmaceutical Press.
17. Sheth AR, Bates S, Muller FX, Grant DJW. 2004. Polymorphism in piroxicam. Cryst Growth Des 4:1091-1098.
18. Grzesiak AL, Lang M, Kim K, Matzger AJ. 2003. Comparison of the four anhydrous polymorphs of carbamazepine and the crystal structure of form I. J Pharm Sci 92:2260-2271.
19. Sheth AR, Zhou D, Muller FX, Grant DJW. 2004. Dehydration kinetics of piroxicam monohydrate and relationship to lattice energy and structure. J Pharm Sci 93:3013-3026.
20. McMahon LE, Timmins P, Williams AC, York P. 1996. Characterization of dihydrates prepared from carbamazepine polymorphs. J Pharm Sci 85:1064-1069.
21. Han J, Suryanarayanan R. 1997. Applications of pressure differential scanning calorimetry in the study of pharmaceutical hydrates I. Carbamazepine dihydrate. Int J Pharm 157:209-218.
22. Allen FH. 2002. The Cambridge Structural Database: A quarter of a million crystal structures and rising. Acta Crystallogr B58:380-388.
23. Kojic-Prodic B, Ruzic-Toros Z. 1982. Structure of piroxicam. Acta Crystallogr B38:2948.
24. Reboul JP, Cristau B, Soyfer JC, Astier JP. 1981. 5H-Dibenz[b,f] azepinecarboxamide-5(Carbamazepine). Acta Crystallogr B37:1844-1848.
25. Ceolin R, Toscani S, Gardette M-F, Agafonov VN, Dzyabchenko AV, Bachet B. 1997. X-ray characterization of the triclinic polymorph of carbamazepine. J Pharm Sci 86:1062-1065.
26. Lefebvre C, Guyot-Hermann AM, Draguet-Brughmans M, Bouche R. 1987. Dissolution rate and polymorphism of carbamazepine: Study of different specialities. Pharm Acta Helv 62:341-347.
27. Reck G, Dietz G, Laban G, Gunther W, Bannier G, Hohne E. 1988. X-ray studies on piroxicam modifications. Pharmazie 43:477-481.
28. Harris RK, Ghi PY, Puschmann H, Apperley DC, Griesser UJ, Hammond RB, Ma C, Roberts KJ, Pearce GJ, Yates JR, Pickard CJ. 2005. Structural studies of the polymorphs of carbamazepine, its dihydrate, and two solvates. Org Process Res Dev 9:902-910.
29. Eriksson L, Johansson E, Kettaneh-Wold N, Wold S. 2001. Multi- and megavariate data analysis. Principles and applications. Umea: Umetrics AB.
30. Workman J, Springsteen A. 1998. Applied spectroscopy, a compact reference for practitioners. London: Academic Press, 539 p.
31. Rantanen J, Wikstrom H, Rhea FE, Taylor LS. 2005. Improved understanding of factors contributing to quantification of anhydrate/hydrate powder mixtures. Appl Spectrosc 59:942-951.
32. Wold S, Sjöström M, Eriksson L. 2001. PLS-regression: A basic tool of chemometrics. Chemom Intell Lab Syst 58:109-130.
33. Krzanowski W, Marriot F. 1995. Multivariate analysis Part 2: Classification, covariance and repeated measurements. London: Arnold.
34. 2O. Acta Crystallogr C40:989-990.
35. Vrecer F, Vrbinc M, Meden A. 2003. Characterization of piroxicam crystal modifications. Int J Pharm 256:3-15.
36. 13C-NMR investigation of the structure of the 1:1 amorphous piroxicam: β-cyclodextrin inclusion compound. Biospectroscopy 5:243-251.
37. Taddei P, Torreggiani A, Simoni R. 2001. Influence of environment on piroxicam polymorphism: Vibrational spectroscopic study. Biopolymers (Biospectroscopy) 62:68-78.
38. 2O. Cryst Res Technol 21:1463-1468.
39. Florence AJ, Kennedy AR, Shankland N, Johnston A. 2004. 5H-Dibenzo(b,f)azepine-5-carboxamide dihydrate. Private Communication.
40. Kaneniwa N, Yamaguchi T, Watari N, Otsuka M. 1984. Hygroscopicity of carbamazepine crystalline powders. Yakugaku Zasshi: J Pharm Soc Jpn 104:184-190.
41. Kala H, Haack U, Pollandt P, Brezesinski G. 1986. Polymorphism of carbamazepine. Acta Pharm Technol 32:72-77.
42. Murphy D, Rodriguez-Cintron F, Langevin B, Kelly RC, Rodriguez-Hornedo N. 2002. Solution-mediated phase transformation of anhydrous to dihydrate carbamazepine and the effect of lattice disorder. Int J Pharm 246:121-134.
43. Strachan CJ, Howell SL, Rades T, Gordon KC. 2004. A theoretical and spectroscopic study of carbamazepine polymorphs. J Raman Spectrosc 35:401-408.
44. Krahn FU, Mielck JB. 1987. Relationships between several polymorphic forms and the dihydrate of carbamazepine. Pharm Acta Helv 62:247-254.
45. Aaltonen J, Kogermann K, Strachan CJ, Rantanen J. 2006. In-line monitoring of solid-state transitions during fluidisation. Chem Eng Sci 62:408-415.
46. Griesser UJ, Burger A. 1995. The effect of water-vapor pressure on desolvation kinetics of caffeine 4/5-hydrate. Int J Pharm 120:83-93.
47. Han J, Suryanarayanan R. 1998. Influence of environmental conditions on the kinetics and mechanism of dehydration of carbamazepine dihydrate. Pharm Dev Technol 3:587-596.
48. Han J, Zhang GGZ, Law D, Wang W, Long MA, Kishi A. 2003. NATAS Annual Conference on Thermal Analysis and Applications , USA.
49. Li Y, Han J, Zhang GGZ, Grant DJW, Suryanarayanan R. 2000. In situ dehydration of carbamazepine dihydrate: A novel technique to prepare amorphous anhydrous carbamazepine. Pharm Dev Technol 5:257-266.