Improvement in chemical and physical stability of fluvastatin drug through hydrogen bonding interactions with different polymer matrices

Current Drug Delivery

Volumn 6, Issue 1, 2009, Pages 101-112

  Papageorgiou, G Z ^a   Papadimitriou, S ^a   Karavas, E ^b   Georgarakis, E ^a   Docoslis, A ^c   Bikiaris, D ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b Pharmaceutical Industry   (Greece)

^c QUEEN S UNIVERSITY   (Canada)

Author keywords

Chitosan; Eudragit; Fluvastatin; Physical and chemical stability; PVP; Solid dispersions

Indexed keywords

CHITOSAN; EUDRAGIT RS; FLUINDOSTATIN; LACTONE; POVIDONE;

ARTICLE; CONTROLLED DRUG RELEASE; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG SOLUBILITY; DRUG STABILITY; DRUG STORAGE; HYDROGEN BOND; INFRARED SPECTROSCOPY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; RAMAN SPECTROMETRY; SCANNING ELECTRON MICROSCOPY; X RAY DIFFRACTION;

CALORIMETRY, DIFFERENTIAL SCANNING; CHITOSAN; DRUG STABILITY; FATTY ACIDS, MONOUNSATURATED; HYDROGEN BONDING; HYDROXYMETHYLGLUTARYL-COA REDUCTASE INHIBITORS; INDOLES; POLYMERS; POLYMETHACRYLIC ACIDS; POVIDONE; X-RAY DIFFRACTION;

EID: 61849145863     PISSN: 15672018     EISSN: None     Source Type: Journal    
DOI: 10.2174/156720109787048230     Document Type: Article

References (51)

1. Langtry, H.D.; Markham, A. Erratum: Fluvastatin: A review of its use in lipid disorders. Drugs, 1999, 57, 583-606.
2. Plosker, G.L.; Wagstaff, A.J. Fluvastatin: A review of its pharmacology and use in the management of hypercholesterolaemia. Drugs, 1996, 51, 433-59.
3. Nakashima, A.; Saxer, C.; Niina, M.; Masuda, N.; Iwasaki, K.; Furukawa, K. Determination of fluvastatin and its five metabolites in human plasma using simple gradient reversed-phase high-performance liquid chromatography with ultraviolet detection. J. Chrom. B. Biom. Sci. Appl. 2001, 760, 17-25
4. Levy, R.I.; Troendle, A.J.; Fattu, J.M. A quarter century of drug treatment of dyslipoproteinemia, with a focus on the new HMG-CoA reductase inhibitor fluvastatin. Circulation, 1993, 87, III45-III53
5. Barilla, D.; Prasad, P.; Hubert. M.; Gumbhir-Shah, K. Steady-state pharmacokinetics of fluvastatin in healthy subjects following a new extended release fluvastatin tablet, Lescol® XL. Biopharm. Drug Dispos., 2004, 25, 51-9.
6. Scharnagl, H.; Vogel, M.; Abletshauser, C.; Freisinger, F.; Stojakovic, T.; März, W. Efficacy and safety of fluvastatin-extended release in hypercholesterolemic patients: Morning administration is equivalent to evening administration. Cardiology, 2006, 106, 241-8.
7. Corsini, A. The use of statins in optimising reduction of cardiovascular risk: Focus on fluvastatin. Int. J. Clin. Pract., 2004, 58, 494-503.
8. Jokubaitis, L.A. Development and pharmacology of fluvastatin. Br. J. Clin. Pract., 1996, 77A, 11-5.
9. Lennernäs, H.; Fager, G. Pharmacodynamics and pharmacokinetics of the HMG-CoA reductase inhibitors. Similarities and differences. Clin. Pharmacokinet., 1997, 32, 403-25.
10. Jemal, M.; Ouyang, Z.; Powell, M.L. Direct-injection LC-MS-MS method for high-throughput simultaneous quantitation of simvastatin and simvastatin acid in human plasma. J. Pharm. Biomed. Anal., 2000, 23, 323-9.
11. Zhao, J.J.; Xie, I.H.; Yang, A.Y.; Roadcap, B.A.; Rogers, J.D. Quantitation of simvastatin and its β-hydroxy acid in human plasma by liquid-liquid cartridge extraction and liquid chromatography/ tandem mass spectrometry. J. Mass Spectrom., 2000, 35, 1133-43.
12. Kaufman, M.J. Rate and equilibrium constants for acid-catalyzed lactone hydrolysis of HMG-CoA reductase inhibitors. Int. J. Pharm., 1990, 66, 97-103.
13. Grabarkiewicz, T.; Grobelny, P.; Hoffmann, M.; Mielcarek, J. DFT study on hydroxy acid-lactone interconversion of statins: The case of fluvastatin. Org. Biomol. Chem., 2006, 4, 4299-306.
14. Taylor, L.S.; Zografi, G. Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions. Pharm. Res., 1997, 14, 1691-8.
15. Matsumoto, T.; Zografi, G. Physical properties of solid molecular dispersions of indomethacin with poly(vinylpyrrolidone) and poly(vinylpyrrolidone-co-vinyl-acetate) in relation to indomethacin crystallization. Pharm. Res., 1999, 16, 1722-8.
16. Pignatello, R.; Ferro, M.; De Guidi, G.; Salemi, G.; Vandelli, M.A.; Guccione, S.; Geppi, M.; Forte, C.; Puglisi, G. Preparation, characterisation and photosensitivity studies of solid dispersions of diflunisal and Eudragit RS100® and RL100®. Int. J. Pharm., 2001, 218, 27-42.
17. Aceves, J.M.; Cruz, R.; Hernandez, E. Preparation and characterization of Furosemide-Eudragit controlled release systems. Int. J. Pharm., 2000, 195, 45-53.
18. Oth, M.P.; Moes, A.J. Sustained release solid dispersions of indomethacin with Eudragit RS and RL Int. J. Pharm., 1989, 55, 157-74.
19. Karavas, E.; Ktistis, G.; Xenakis, A.; Georgarakis, E. Miscibility behavior and formation mechanism of stabilized felodipine-polyvinylpyrrolidone amorphous solid dispersions. Drug Dev. Ind. Pharm., 2005, 31, 473-89.
20. Yamashita, K.; Nakate, T.; Okimoto, K.; Ohike, A.; Tokunaga, Y.; Ibuki, R.; Higaki, K.; Kimura, T. Establishment of new preparation method for solid dispersion formulation of tacrolimus. Int. J. Pharm., 2003, 267, 79-91.
21. Bikiaris, D.; Papageorgiou, G.Z.; Stergiou, A.; Pavlidou, E.; Karavas, E.; Kanaze, F.; Georgarakis, M. Physicochemical studies on solid dispersions of poorly water-soluble drugs: Evaluation of capabilities and limitations of thermal analysis techniques. Thermochim. Acta, 2005, 439, 58-67.
22. Ye, G.; Wang, S.; Heng, P.W.S.; Chen, L.; Wang, C. Development and optimization of solid dispersion containing pellets of itraconazole prepared by high shear pelletization. Int. J. Pharm., 2007, 337, 80-7.
23. Karavas, E.; Georgarakis, E.; Sigalas, M.P.; Avgoustakis, K.; Bikiaris, D. Investigation of the release mechanism of a sparingly water-soluble drug from solid dispersions in hydrophilic carriers based on physical state of drug, particle size distribution and drug-polymer interactions. Eur. J. Pharm. Biopharm., 2007, 66, 334-47.
24. Karavas, E.; Georgarakis, E.; Bikiaris, D. Felodipine nanodispersions as active core for predictable pulsatile chronotherapeutics using PVP/HPMC blends as coating layer. Int. J. Pharm., 2006, 313, 189-97.
25. Karavas, E.; Georgarakis, M.; Docoslis, A.; Bikiaris D. Combining SEM, TEM, and micro-Raman techniques to differentiate between the amorphous molecular level dispersions and nanodispersions of a poorly water-soluble drug within a polymer matrix. Int. J. Pharm., 2007, 340, 76-83.
26. Huang, J.; Wigent, R.J.; Bentzley, C.M.; Schwartz, J.B. Nifedipine solid dispersion in microparticles of ammonio methacrylate copolymer and ethylcellulose binary blend for controlled drug delivery. Effect of drug loading on release kinetics. Int. J. Pharm., 2006, 319, 44-54.
27. Ritthidej, G.C.; Chomto, P.; Pummangura, S.; Menasveta, P. Chitin and chitosan as disintegrants in paracetamol tablets. Drug Dev. Ind. Pharm., 1994, 20, 2109-34.
28. Imai, T.; Shiraishi, S.; Saito, H.; Otagiri, M. Interaction of indomethacin with low molecular weight chitosan, and improvements of some pharmaceutical properties of indomethacin by low molecular weight chitosans. Int. J. Pharm., 1991, 67, 11-20.
29. Chen, R.; Takahashi, H.; Okamoto, H.; Danjo, K. Particle design of three-component system for sustained release using a 4-fluid nozzle spray-drying technique. Chem. Pharm. Bull., 2006, 54, 1486-90.
30. Jawalkar, S.S.; Raju, K.V.S.N.; Halligudi, S.B.; Sairam, M.; Aminabhavi, T.M. Molecular modeling simulations to predict compatibility of poly(vinyl alcohol) and chitosan blends: A comparison with experiments. J. Phys. Chem. B, 2007, 111, 2431-9.
31. Takahashi, H.; Chen, R.; Okamoto, H.; Danjo, K. Preparation of dry powder inhalation with lactose carrier particles surface-coated using a Wurster fluidized bed. Chem. Pharm. Bull., 2005, 53, 37-41.
32. Gurusamy, S.; Kumar, V.; Mishra, D.N. Preparation, characterization and in vitro dissolution studies of solid systems of valdecoxib with chitosan. Chem. Pharm. Bull., 2006, 54, 1102-6.
33. Tantishaiyakul, V.; Kaewnopparat, N.; Ingkatawornwong, S. Properties of solid dispersions of piroxicam in polyvinylpyrrolidone. Int. J. Pharm., 1999, 181, 143-51.
34. Van den Mooter, G.; Wuyts, M.; Blaton, N.; Busson, R.; Grobet, P.; Augustijns, P.; Kinget, R. Physical stabilisation of amorphous ketoconazole in solid dispersions with polyvinylpyrrolidone K25. Eur. J. Pharm. Sci., 2001, 12, 261-9.
35. Ruan, L.R.; Yu, B.Y.; Fu, G.M.; Zhu, D.N. Improving the solubility of ampelopsin by solid dispersions and inclusion complexes. J. Pharm. Biom. Anal., 2005, 38, 457-64
36. Gupta, P.; Bansal. A.K. Spray drying for generation of a ternary amorphous system of celecoxib, PVP, and meglumine. Pharm. Dev. Technol., 2005, 10, 273-81.
37. Corrigan, O. I., Holohan, E. M. Amorphous spray-dried hydroflumethiazide-polyvinylpyrrolidone systems: Physicochemical properties. J. Pharm. Pharmacol., 1984, 36, 217-21.
38. Aso, Y.; Yoshioka, S.; Kojima, S. Molecular Mobility-Based Estimation of the Crystallization Rates of Amorphous Nifedipine and Phenobarbital in Poly(vinylpyrrolidone) Solid Dispersions. J. Pharm. Sci., 2004, 93, 384-91.
39. Papageorgiou, G.Z;. Bikiaris, D.; Karavas, E.; Stergiou, A.; Georgarakis, E. Tailoring the release rates of fluconazole using solid dispersions in polymer blends. Drug Dev. Ind. Pharm., 2008, 34, 336-46.
40. Kanaze, F.I.; Kokkalou, E.; Niopas, I.; Georgarakis, M.; Stergiou, A.; Bikiaris, D. Dissolution enhancement of flavonoids by solid dispersion in PVP and PEG matrixes: A comparative study. J. Appl. Polym. Sci., 2006, 102, 460-71.
41. Karavas, E.; Georgarakis, E.; Bikiaris, D.; Thomas, T.; Katsos V.; Xenakis, A. Hydrophilic matrices as carriers in felodipine solid dispersion systems. Progr. Colloid Polym. Sci., 2001, 118, 149-52.
42. Yoshioka, S.; Aso, Y. Correlations between molecular mobility and chemical stability during storage of amorphous pharmaceuticals. J. Pharm. Sci., 2007, 96, 960-81.
43. Duddu, S.P.; Dal Monte, P.R. Effect of glass transition temperature on the stability of lyophilized formulations containing a chimeric therapeutic monoclonal antibody. Pharm. Res., 1997, 14, 591-5.
44. Alhneck, C.; Zografi, G. The molecular basis of moisture effects on the physical and chemical stability of drugs in the solid state. Int. J. Pharm., 1990, 62, 87-95.
45. Fitzpatrick, S.; McCabe, J.F.; Petts, C.R.; Booth S.W. Effect of moisture on polyvinylpyrrolidone in accelerated stability testing. Int. J. Pharm. 2002, 246, 143-51.
46. Ghebremeskel, A.N.; Vemavarapu, C.; Lodaya, M. Use of surfactants as plasticizers in preparing solid dispersions of poorly soluble API: Stability testing of selected solid dispersions. Pharm. Res., 2006, 23, 1928-36.
47. Christensen, K.L.; Pedersen, G.P.; Kristensen, H.G. Physical stability of redispersible dry emulsions containing amorphous sucrose. Eur. J. Pharm. Biopharm., 2002, 53, 147-53.
48. Hu, J.; Johnston, K.P.; Williams R.O. Stable amorphous danazol nanostructured powders with rapid dissolution rates produced by spray freezing into liquid. Drug Dev. Ind. Pharm., 2004, 30, 695-704.
49. Hirasawa, N.; Ishise, S.; Miyata, H.; Danjo, K. Application of nilvadipine solid dispersion to tablet formulation and manufacturing using crospovidone and methylcellulose as dispersion carriers. Chem. Pharm. Bull., 2004, 52, 244-7.
50. Wu, C.; McGinity, J.W. Influence of ibuprofen as a solid-state plasticizer in Eudragit® RS 30 D on the physicochemical properties of coated beads. AAPS Pharm. Sci. Tech., 2001, 2, article 24.
51. Lin-Vien, D.; Colthup, N.B.; Fateley, W.G.; Grasselli, J.G. The handbook of Infrared and Raman characteristsic frequencies of Organic Molacules. Academic Press, San Diego USA, 1991.