Biorelevant characterisation of amorphous furosemide salt exhibits conversion to a furosemide hydrate during dissolution

International Journal of Pharmaceutics

Volumn 457, Issue 1, 2013, Pages 14-24

  Nielsen, Line Hagner ^a   Gordon, Sarah ^a   Pajander, Jari Pekka ^a   Østergaard, Jesper ^a   Rades, Thomas ^a   Müllertz, Anette ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Amorphous form; Biorelevant dissolution; Furosemide; Raman flow through dissolution; Solid state conversion; UV imaging

Indexed keywords

FUROSEMIDE; SODIUM;

ARTICLE; COMPARATIVE STUDY; DISSOLUTION; IMAGING SYSTEM; IN VITRO STUDY; PARTIAL LEAST SQUARES REGRESSION; PRIORITY JOURNAL; RAMAN SPECTROMETRY; SMALL INTESTINE; SOLID STATE; THERMOGRAVIMETRY; ULTRAVIOLET RADIATION;

AMORPHOUS FORM; BIORELEVANT DISSOLUTION; FUROSEMIDE; RAMAN FLOW THROUGH DISSOLUTION; SOLID STATE CONVERSION; UV IMAGING;

ACIDS; CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; FUROSEMIDE; HYDROGEN-ION CONCENTRATION; INTESTINAL SECRETIONS; PHOSPHATIDYLCHOLINES; SALTS; SOLUBILITY; TAUROCHOLIC ACID;

EID: 84884919663     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2013.08.029     Document Type: Article

References (43)

1. J. Aaltonen, P. Heinanen, L. Peltonen, H. Kortejarvi, V.P. Tanninen, L. Christiansen, J. Hirvonen, J. Yliruusi, and J. Rantanen In situ measurement of solvent-mediated phase transformations during dissolution testing J. Pharm. Sci. 95 2006 2730 2737 (Pubitemid 46093179)
2. D.E. Alonzo, G.G. Zhang, D. Zhou, Y. Gao, and L.S. Taylor Understanding the behavior of amorphous pharmaceutical systems during dissolution Pharm. Res. 27 2010 608 618
3. G.L. Amidon, H. Lennernas, V.P. Shah, and J.R. Crison A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability Pharm. Res. 12 1995 413 420
4. A. Avdeef, and O. Tsinman Miniaturized rotating disk intrinsic dissolution rate measurement: effects of buffer capacity in comparisons to traditional wood's apparatus Pharm. Res. 25 2008 2613 2627
5. J.P. Boetker, M. Savolainen, V. Koradia, F. Tian, T. Rades, A. Mullertz, C. Cornett, J. Rantanen, and J. Ostergaard Insights into the early dissolution events of amlodipine using UV imaging and Raman spectroscopy Mol. Pharm. 8 2011 1372 1380
6. P. Cardew, and R.J. Davey The kinetics of solvent-mediated phase transformation Proc. R. Soc. Lond. A 398 1985 415 428
7. N. Chieng, T. Rades, and D. Saville Formation and physical stability of the amorphous phase of ranitidine hydrochloride polymorphs prepared by cryo-milling Eur. J. Pharm. Biopharm. 68 2008 771 780 (Pubitemid 351318218)
8. Y. Chikaraishi, M. Otsuka, and Y. Matsuda Dissolution phenomenon of the piretanide amorphous form involving phase change Chem. Pharm. Bull. 44 1996 2111 2115 (Pubitemid 26396763)
9. J.B. Dressman, G.L. Amidon, C. Reppas, and V.P. Shah Dissolution testing as a prognostic tool for oral drug absorption: immediate release dosage forms Pharm. Res. 15 1998 11 22 (Pubitemid 28080861)
10. E. Galia, E. Nicolaides, D. Horter, R. Lobenberg, C. Reppas, and J.B. Dressman Evaluation of various dissolution media for predicting in vivo performance of classes I and II drugs Pharm. Res. 15 1998 698 705 (Pubitemid 28275645)
11. S. Gordon, K. Naelapaa, J. Rantanen, A. Selen, A. Mullertz, and J. Ostergaard Real-time dissolution behavior of furosemide in biorelevant media as determined by UV imaging Pharm. Dev. Technol. 2012 (Epub ahead of print)
12. G.E. Granero, M.R. Longhi, M.J. Mora, H.E. Junginger, K.K. Midha, V.P. Shah, S. Stavchansky, J.B. Dressman, and D.M. Barends Biowaiver monographs for immediate release solid oral dosage forms: furosemide J. Pharm. Sci. 99 2010 2544 2556
13. V. Gray, G. Kelly, M. Xia, C. Butler, S. Thomas, and S. Mayock The science of USP 1 and 2 dissolution: present challenges and future relevance Pharm. Res. 26 2009 1289 1302
14. K. Greco, and R. Bogner Crystallization of amorphous indomethacin during dissolution: effect of processing and annealing Mol. Pharm. 7 2010 1406 1418
15. K. Greco, D.P. Mcnamara, and R. Bogner Solution-mediated phase transformation of salts during dissolution: investigation using haloperidol as a model drug J. Pharm. Sci. 100 2011 2755 2768
16. P. Guerrieri, A.C. Rumondor, T. Li, and L.S. Taylor Analysis of relationships between solid-state properties, counterion, and developability of pharmaceutical salts AAPS PharmSciTech 11 2010 1212 1222
17. B.C. Hancock, and G. Zografi Characteristics and significance of the amorphous state in pharmaceutical systems J. Pharm. Sci. 86 1997 1 12
18. D. Horter, and J.B. Dressman Influence of physicochemical properties on dissolution of drugs in the gastrointestinal tract Adv. Drug Deliv. Rev. 46 2001 75 87
19. W.L. Hulse, J. Gray, and R.T. Forbes A discriminatory intrinsic dissolution study using UV area imaging analysis to gain additional insights into the dissolution behaviour of active pharmaceutical ingredients Int. J. Pharm. 434 2012 133 139
20. V. Iannuccelli, G. Coppi, E. Leo, F. Fontana, and M.T. Bernabei PVP solid dispersions for the controlled release of furosemide from a floating multiple-unit system Drug Dev. Ind. Pharm. 26 2000 595 603 (Pubitemid 30317065)
21. K. Kleberg, J. Jacobsen, and A. Mullertz Characterising the behaviour of poorly water soluble drugs in the intestine: application of biorelevant media for solubility, dissolution and transport studies J. Pharm. Pharmacol. 62 2010 1656 1668
22. S. Klein The use of biorelevant dissolution media to forecast the in vivo performance of a drug AAPS J. 12 2010 397 406
23. D. Law, E.A. Schmitt, K.C. Marsh, E.A. Everitt, W. Wang, J.J. Fort, S.L. Krill, and Y. Qiu Ritonavir-PEG 8000 amorphous solid dispersions: in vitro and in vivo evaluations J. Pharm. Sci. 93 2004 563 570 (Pubitemid 38332289)
24. P.J. Marsac, H. Konno, and L.S. Taylor A comparison of the physical stability of amorphous felodipine and nifedipine systems Pharm. Res. 23 2006 2306 2316 (Pubitemid 44511511)
25. Y. Matsuda, and E. Tatsumi Physiochemical characterization of furosemide modifications Int. J. Pharm. 60 1990 11 26
26. M. McAllister Dynamic dissolution: a step closer to predictive dissolution testing? Mol. Pharm. 7 2010 1374 1387
27. K.R. Morris, U.J. Griesser, C.J. Eckhardt, and J.G. Stowell Theoretical approaches to physical transformations of active pharmaceutical ingredients during manufacturing processes Adv. Drug Deliv. Rev. 48 2001 91 114 (Pubitemid 32452293)
28. D.M. Mudie, G.L. Amidon, and G.E. Amidon Physiological parameters for oral delivery and in vitro testing Mol. Pharm. 7 2010 1388 1405
29. L.H. Nielsen, S. Gordon, R. Holm, A. Selen, T. Rades, and A. Mullertz Preparation of an amorphous sodium furosemide salt improves solubility and dissolution rate and leads to a faster Tmax after oral dosing to rats Eur. J. Pharm. Biopharm. 2013 (in press)
30. A. Noyes, and W. Whitney The rate of solution of solid substances in their own solutions J. Am. Chem. Soc. 19 1897 930 934
31. J. Ostergaard, E. Meng-Lund, S.W. Larsen, C. Larsen, K. Petersson, J. Lenke, and H. Jensen Real-time UV imaging of nicotine release from transdermal patch Pharm. Res. 27 2010 2614 2623
32. J. Ostergaard, F. Ye, J. Rantanen, A. Yaghmur, S.W. Larsen, C. Larsen, and H. Jensen Monitoring lidocaine single-crystal dissolution by ultraviolet imaging J. Pharm. Sci. 100 2011 3405 3410
33. M. Otsuka, R. Teraoka, and Y. Matsuda Rotating-disk dissolution kinetics of nitrofurantoin anhydrate and monohydrate at various temperatures Pharm. Res. 9 1992 307 311
34. J.E. Patterson, M.B. James, A.H. Forster, and T. Rades Melt extrusion and spray drying of carbamazepine and dipyridamole with polyvinylpyrrolidone/vinyl acetate copolymers Drug Dev. Ind. Pharm. 34 2008 95 106 (Pubitemid 351156956)
35. L. Perioli, G. D'Alba, and C. Pagano New oral solid dosage form for furosemide oral administration Eur. J. Pharm. Biopharm. 80 2012 621 629
36. N. Qiao, K. Wang, W. Schlindwein, A. Davies, and M. Li In situ monitoring of carbamazepine-nicotinamide cocrystal intrinsic dissolution behaviour Eur. J. Pharm. Biopharm. 83 2013 415 426
37. A. Saleki-Gerhardt, C. Ahlneck, and G. Zografi Assessment of disorder in crystalline solids Int. J. Pharm. 101 1994 237 247 (Pubitemid 24025158)
38. M. Savolainen, K. Kogermann, A. Heinz, J. Aaltonen, L. Peltonen, C. Strachan, and J. Yliruusi Better understanding of dissolution behaviour of amorphous drugs by in situ solid-state analysis using Raman spectroscopy Eur. J. Pharm. Biopharm. 71 2009 71 79
39. E. Shefter, and T. Higuchi Dissolution behavior of crystalline solvated and nonsolvated forms of some pharmaceuticals J. Pharm. Sci. 52 1963 781 791
40. V.M. Sonje, L. Kumar, V. Puri, G. Kohli, A.M. Kaushal, and A.K. Bansal Effect of counterions on the properties of amorphous atorvastatin salts Eur. J. Pharm. Sci. 44 2011 462 470
41. C.S. Towler, T. Li, H. Wikstrom, D.M. Remick, M.V. Sanchez-Felix, and L.S. Taylor An investigation into the influence of counterion on the properties of some amorphous organic salts Mol. Pharm. 5 2008 946 955
42. L. Yu Amorphous pharmaceutical solids: preparation, characterization and stabilization Adv. Drug Deliv. Rev. 48 2001 27 42 (Pubitemid 32454482)
43. Zhang, G.G., Law, D., Schmitt, E.A., Qiu, Y., 2004. Phase transformation considerationsduring process development and manufacture of solid oral dosage forms. Adv.Drug Deliv. Rev. 56, 371-390. (Pubitemid 38202329)