Conformational study of ketoprofen by combined DFT calculations and Raman spectroscopy

International Journal of Pharmaceutics

Volumn 307, Issue 1, 2006, Pages 56-65

  Vueba, M L ^a   Pina, M E ^a   Veiga, F ^a   Sousa, J J ^a   De Carvalho, L A E Batista ^b  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

Conformational analysis; DFT calculations; FTIR spectroscopy; Ketoprofen; Raman spectroscopy; Rotational isomerism

Indexed keywords

KETOPROFEN;

ANALYTIC METHOD; ARTICLE; DENSITY FUNCTIONAL THEORY; DIMERIZATION; DRUG CONFORMATION; DRUG STRUCTURE; GEOMETRY; HYDROGEN BOND; PRIORITY JOURNAL; RAMAN SPECTROMETRY; SOLID STATE;

EID: 28844453016     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2005.09.019     Document Type: Article

References (62)

1. B. Avouac, and M. Teule Ketoprofen: the European experience J. Clin. Pharmacol. 28 1988 S2 S7
2. L.A.E. Batista de Carvalho, J.J.C. Teixeira-Dias, and R. Fausto The CH3CH2 internal rotation in thiopropionic acid as studied by ab initio SCF-MO method J. Mol. Struct. (Theochem.) 208 1990 109 121
3. A. Becke Density-functional exchange-energy approximation with correct asymptatic behavior Phys. Rev. A38 1988 3098
4. A. Becke Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 98 1993 5648
5. J. Breienbach, W. Schrof, and J. Neumann Confocal Raman-spectroscopy: analytical approach to solid dispersions and mapping of drugs Pharm. Res. 16 1999 1109 1113
6. P. Briard, and J.C. Rossi Kétoprofène Acta Cryst. C46 1990 1036 1038
7. S.R. Byrn, R.R. Pfeiffer, G. Stephenson, D.J.W. Grant, and W.B. Gleason Solid-state pharmaceutical chemistry Chem. Mater. 6 1994 1148 1158
8. S.R. Byrn, R.R. Pfeiffer, M. Ganey, C. Hoiberg, and G. Pochikian Pharmaceutical solids: a strategic approach to regulatory considerations Pharm. Res. 12 1995 945 954
9. I. Caruso, E. Frigerio, M. Fumagalli, C. Liverta, L. Moro, and V. Tamassia Bioavailability study on a new slow-release formulation of ketoprofen J. Int. Med. Res. 10 1982 229 233
10. B.J. Cathcart, J.D. Vince, A.J. Gordon, M. Bell, and I.M. Chalmers Studies on 2-(3-benzoylphenyl) propionic acid ('Orudis') Ann. Rheum. Dis. 32 1973 62 65
11. S.-H. Choi, S.-Y. Kim, J.J. Ryoo, J.Y. Park, and K.-P. Lee FT-Raman and FT-IR spectra of the non-steroidal antiinflammatory drug ketoprofen included in cyclodextrins Anal. Sci. 17 2001 i785 i788
12. M.C. Davies, J.S. Binns, C.D. Melia, P.J. Hendra, D. Bourgeois, S.P. Chruch, and P.J. Stephenson FT Raman spectroscopy of drugs in polymers Int. J. Pharm. 66 1990 223 232
13. M.C. Davies, J.S. Binns, C.D. Melia, and D. Bourgeois Fourier transform raman spectroscopy of polymeric biomaterials and drug delivery systems Spectrochim. Acta 46A 1990 277 283
14. T.R.M. De Beer, G.J. Vergote, W.R.G. Baeyens, J.P. Remon, C. Vervaet, and F. Verpoort Development and validation of a direct, non-destructive quantitative method for medroxyprogestererone acetate in a pharmaceutical suspension using FT-Raman spectroscopy Eur. J. Pharm. Sci. 23 2004 355 362
15. C.M. Deeley, R.A. Spragg, and T.L. Threalfall A comparison of Fourier transform infrared and near-infrared Fourier transform raman spectroscopy for quantitative measurements: an application in polymorphism Spectrochim. Acta 47A 1991 1217 1223
16. G.R. Desiraju, and T. Steiner The Weak Hydrogen Bond in Structural Chemistry and Biology. IUCr Monographs on Crystallography, vol. 9 1999 Oxford University Press
17. W.P. Findlay, and D.E. Bugay Utilization of Fourier transform-Raman spectroscopy for the study of pharmaceutical crystal forms J. Pharm. Biomed. Anal. 16 1998 921 930
18. A. Forster, K. Gordon, D. Schmierer, N. Soper, V. Wu, and T. Rades Characterisation of two polymorphic forms of Ranitine-HCl Internet J. Vibrational Spectrosc. 2 2 1999 12
19. J. Fossgreen Ketoprofen-survey of current publications Scand. J. Rheumatol. 1976 7 32
20. J. Fossgreen, B. Kirchheiner, F.O. Petersen, E. Tophøj, and E. Zachariae Clinical evaluation of ketoprofen (19.583 R.P.) in rheumatoid arthritis-double-blind cross-over comparision with indomethacin Scand. J. Rheumatol. 1976 93 98
21. Frisch, M.J., et al., 1998. Gaussian 98W, Revision A.9. Gaussian, Inc., Pittsburgh, PA.
22. P. Giunchedi, L. Maggi, U. Conte, and C. Caramella Ketoprofen pulsatile absorption from 'multiple unit' hydrophilic matrices Int. J. Pharm. 77 1991 177 181
23. M.J. Habib, and R. Meuse Development of controlled release formulations of ketorpofen for oral use Drug Dev. Ind. Pharm. 21 1995 1463 1472
24. P.C. Hariharan, and J.A. Pople The influence of polarization functions on molecular orbital hydrogenation energies Theor. Chim. Acta 28 1973 213
25. G.W. Houghton, M.J. Dennis, E.D. Rigler, and R.L. Parsons Comparative pharmacokinetics of ketoprofen derived from single oral doses of ketoprofen capsules or a novel sustained-release pellet formulation Biopharm. Drug Dispos. 5 1984 203 209
26. G.W. Houghton, M.J. Dennis, R. Templelon, R.M. Calvert, and D.G. Cresswell A pharmacokinetic study of repeated doses of a new controlled release of ketoprofen Int. Clin. Pharm. Ther. 23 1984 131 133
27. L. Julou, J.C. Guyonnet, R. Ducrot, J. Fournel, and J. Pasquet Ketoprofen (19.583 R.P.) (2-(3-benzoylphenyl)-propionic acid). Main pharmacological properties: outline of toxicological and pharmacokinetic data Scand. J. Rheumatol. 1976 33 44
28. S.G. Kazarian, and G.G. Martirosyan Spectroscopy of polymer/drug formulations processed with supercritical fluids: in situ ATR-IR and Raman study of impregnation of ibuprofen into PVP Int. J. Pharm. 232 2002 81 90
29. M.A. Khan, J. Dib, and I.K. Reedy Statistical optimization of ketoprofen-eudragit S100 coprecipitates to obtain controlled release tablets Drug Dev. Ind. Pharm. 22 1996 135 141
30. C. Lee, W. Yang, and R.G. Parr Development of the Colle-Salvetti correlation-energy formulation into a functional of the electron density Phys. Rev. B37 1988 785
31. A. Le Liboux, M. Teule, A. Frydman, B. Osterhuis, and J.H.G. Jonkman Effect of diet on the single- and multiple-dose pharmacokinetics of sustained-release ketoprofen Eur. J. Clin. Pharmacol. 47 1994 361 366
32. R. Marcolongo, M. Rubegni, D. Provvedi, N. Giordano, E. Frati, and G. Bruni A double-blind, interpatient comparison of plain and slow-release ketoprofen in osteoarthritis Int. J. Clin. Pharm. Ther. 22 1984 377 381
33. M.P.M. Marques, P.J. Oliveira, A.J.M. Moreno, and L.A.E. Batista de Carvalho Study of carvedilol by combined Raman spectroscopy and ab initio MO calculations J. Raman Spectrosc. 33 2002 778 783
34. Martindale The Extra Pharmacopeia 1996 The Pharmaceutical Press London
35. B. Miehlich, A. Savin, H. Stoll, and H. Preuss Results obtained with the correlation energy density functionals of Becke and Lee, Yang and Parr Chem. Phys. Lett. 157 1989 200
36. F.A. Miller, and B.M. Harney Variable temperature sample holder for Raman spectroscopy Appl. Spectrosc. 24 1970 291 292
37. K.D. Morley, R.M. Bernstein, G.R.V. Hughes, C.M. Black, C.A.N. Rajapakse, and L. Wilson A comparative trial of a controlled-release formulation of ketoprofen ('oruvail') and a conventional capsule formulation of ketoprofen ('orudis') in patients with osteoarthritis of the hip Curr. Med. Res. Opin. 9 1984 28 34
38. R. Mullangi, M. Yao, and N.R. Srinivas Resolution of enantiomers of ketoprofen by HPLC a review Biomed. Chromatogr. 17 2003 423 434
39. T.M. Niemczyk, M. Delgado-Lopez, J.T. Allen, and D.L. Arneberg Quantitative assay of bucindolol in gel capsules using infrared and Raman spectroscopy Appl. Spectrosc. 4 1998 513 518
40. G.F. Palmieri, G. Bonacucina, P. Di Martino, and S. Martilli Microencapsulation of semisolid ketoprofen/polymer microspheres Int. J. Pharm. 242 2002 175 178
41. C. Parejo, A. Gallardo, and J. San Roman Controlled release of NSAIDs bound to polyacrylic carrier systems J. Mater. Sci. Mater. Med. 9 1998 803 809
42. C. Peng, P.Y. Ayala, H.B. Schlegel, and M.J. Frisch Using redundant internal coordinates to optimize equilibrium geometries and transition states J. Comput. Chem. 17 1996 49
43. A. Roda, L. Sabatini, M. Mirasoli, M. Baraldini, and E. Roda Biovailability of a new ketoprofen formulation for once-daily oral administration Int. J. Pharm. 241 2002 165 172
44. A.P. Scott, and L. Radom Harmonic vibrational frequencies: an evaluation of Hartree-Fock, Møller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors J. Phys. Chem. 100 1996 16502 16513
45. A.B. Scranton, B. Drescher, E.W. Nelson, and J.L. Jacobs Use of infrared and Raman spectroscopy for characterization of controlled release systems D.L. Wise Handbook of Pharmaceutical Controlled Release Technology 2000 Marcel Dekker, Inc. New York 131 153 (Chapter 7)
46. K. Siam, V.J. Klimkowski, J.D. Ewbank, L. Schäfer, and C. Van Alsenoy Ab initio studies of structural features not easily amenable to experiment. 38. Structural and conformational investigations of propanoic, 2-methylpropanoic, and butanoic acid J. Comput. Chem. 5 1984 451 456
47. S. Stiegler, M. Birkel, V. Jost, R. Lange, P.W. Lücker, and N. Wetzelsberger Pharmacokinetics and relative bioavailability after single dose administration of 25 mg ketoprofen solution as compared to tablets Methods Find. Exp. Clin. Pharmacol. 17 1995 129 134
48. R. Szostak, and S. Mazurek Quantitative determination of acetylsalicylic acid and acetaminophen in tablets by FT-Raman spectroscopy Analyst 127 2002 144 148
49. L.S. Taylor, and G. Zografi Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions Pharm. Res. 14 1997 1691 1698
50. L.S. Taylor, and G. Zografi The quantitative analysis of crystallinity using FT-Raman spectroscopy Pharm. Res. 15 1998 755 761
51. L.S. Taylor, and F.W. Langkilde Evaluation of solid-state forms present in tablets by Raman spectroscopy J. Pharm. Sci. 89 2000 1342 1353
52. 2C(X)YH (X, YO or S) J. Comput. Chem. 12 1991 1047 1057
53. A.M. Tudor, S.J. Church, P.J. Hendra, M.C. Davies, and C.D. Melia The qualitative and quantitative analysis of chlorpropamide polymorphic mixtures by near-infrared Fourier transform raman spectroscopy Pharm. Res. 10 1993 1772 1776
54. B.B. Vargaftig, and N. Dao Relative of vasoactive substances from guinea-pig lungs by slow-reacting substance C and arachidonic acid. Its blockade by nonsteroid anti-inflammatory agents Pharmacology 6 1971 99 108
55. T. Vankeirsbilck, A. Vercauteren, W. Baeyens, and D.W. Van Applications of Raman spectroscopy in pharmaceutical analysis Trends Anal. Chem. 12 2002 869 877
56. Varsányi, G., 1974. Assignments for Vibrational Spectra of Seven Hundred Benzene Derivatives. Akdémiai Kiadó, Budapest/Adam Hilger Ltd., London.
57. G.J. Vergote, C. Vervaet, I. Van Driessche, S. Hoste, S. De Smedt, J. Demeester, R.A. Jain, S. Ruddy, and J.P. Remon An oral controlled release matrix pellet formulation containing nanocrystalline ketoprofen Int. J. Pharm. 219 2001 81 87
58. G.J. Vergote, C. Vervaet, J.P. Remon, T. Haemers, and F. Verpoort Near-infrared FT-Raman spectroscopy as a rapid analytical tool for the determination of diltiazem hydrochloride in tablets Eur. J. Pharm. Sci. 16 2002 63 67
59. G.J. Vergote, T.R.M. De Beer, C. Vervaet, J.P. Remon, W.R.G. Baeyens, N. Diericx, and F. Verpoort In-line monitoring of a pharmaceutical blending process using FT-Raman spectroscopy Eur. J. Pharm. Sci. 21 2004 479 485
60. M.L. Vueba, L.A.E. Batista de Carvalho, F. Veiga, J.J. Sousa, and M.E. Pina Influence of cellulose ether polymers on ketoprofen release from hydrophilic matrix tablets Eur. J. Pharm. Biopharm. 58 2004 51 59
61. P.J. Watts, A. Tudor, S.J. Church, P.J. Hendra, P. Turner, C.D. Melia, and M.C. Davies Fourier transform Raman spectroscopy for the qualitative and quantitative characterization of sulfasalazine-containing polymeric microspheres Pharm. Res. 8 1991 1323 1328
62. E.B. Wilson Jr. The normal modes and frequencies of vibration of regular plane hexagon model of benzene molecule Phys. Rev. 45 1934 706 714