Development of high-energy amorphous solid dispersion of nanosized nobiletin, a citrus polymethoxylated flavone, with improved oral bioavailability

Journal of Pharmaceutical Sciences

Volumn 100, Issue 9, 2011, Pages 3793-3801

  Onoue, Satomi ^a   Uchida, Atsushi ^a   Takahashi, Haruki ^a   Seto, Yoshiki ^a   Kawabata, Yohei ^a   Ogawa, Kazunori ^b   Yuminoki, Kayo ^c   Hashimoto, Naofumi ^c   Yamada, Shizuo ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b NATIONAL INSTITUTE OF FRUIT TREE SCIENCE   (Japan)

^c SETSUNAN UNIVERSITY   (Japan)

Author keywords

Amorphous; Bioavailability; Dissolution; Distribution; Formulation; Solid dispersion

Indexed keywords

NOBILETIN;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DISPERSION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG FORMULATION; DRUG SOLUBILITY; MALE; NONHUMAN; PARTICLE SIZE; PHYSICAL CHEMISTRY; RAT;

EID: 79960142995     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22585     Document Type: Article

References (26)

1. Walle T. 2007. Methoxylated flavones, a superior cancer chemopreventive flavonoid subclass? Semin Cancer Biol 17(5):354-362.
2. Nakajima A, Yamakuni T, Matsuzaki K, Nakata N, Onozuka H, Yokosuka A, Sashida Y, Mimaki Y, Ohizumi Y. 2007. Nobiletin, a citrus flavonoid, reverses learning impairment associated with N-methyl-d-aspartate receptor antagonism by activation of extracellular signal-regulated kinase signaling. J Pharmacol Exp Ther 321(2):784-790.
3. Onozuka H, Nakajima A, Matsuzaki K, Shin RW, Ogino K, Saigusa D, Tetsu N, Yokosuka A, Sashida Y, Mimaki Y, Yamakuni T, Ohizumi Y. 2008. Nobiletin, a citrus flavonoid, improves memory impairment and Abeta pathology in a transgenic mouse model of Alzheimer's disease. J Pharmacol Exp Ther 326(3):739-744.
4. Nagase H, Yamakuni T, Matsuzaki K, Maruyama Y, Kasahara J, Hinohara Y, Kondo S, Mimaki Y, Sashida Y, Tank AW, Fukunaga K, Ohizumi Y. 2005. Mechanism of neurotrophic action of nobiletin in PC12D cells. Biochemistry 44(42):13683-13691.
5. Matsuzaki K, Yamakuni T, Hashimoto M, Haque AM, Shido O, Mimaki Y, Sashida Y, Ohizumi Y. 2006. Nobiletin restoring beta-amyloid-impaired CREB phosphorylation rescues memory deterioration in Alzheimer's disease model rats. Neurosci Lett 400(3):230-234.
6. Yamakuni T, Nakajima A, Ohizumi Y. 2010. [Preventive action of nobiletin, a constituent of AURANTII NOBILIS PERICARPIUM with anti-dementia activity, against amyloid-beta peptide-induced neurotoxicity expression and memory impairment]. Yakugaku Zasshi 130(4):517-520.
7. Yao J, Lu Y, Zhou JP 2008. Preparation of nobiletin in self-microemulsifying systems and its intestinal permeability in rats. J Pharm Pharm Sci 11(3):22-29.
8. Yao J, Zhou JP, Ping QN, Lu Y, Chen L. 2008. Distribution of nobiletin chitosan-based microemulsions in brain following i.v. injection in mice. Int J Pharm 352(1-2):256-262.
9. Lin W, Yao J, Zhou JP. 2009. [Preparation of self-assemble nobiletin proliposomes and its pharmacokinetics in rats]. Yao Xue Xue Bao 44(2):192-196.
10. Kawabata Y, Yamamoto K, Debari K, Onoue S, Yamada S. 2010. Novel crystalline solid dispersion of tranilast with high photostability and improved oral bioavailability. Eur J Pharm Sci 39(4):256-262.
11. Onoue S, Sato H, Kawabata Y, Mizumoto T, Hashimoto N, Yamada S. 2009. In vitro and in vivo characterization on amorphous solid dispersion of cyclosporine A for inhalation therapy. J Control Release 138:16-23.
12. Onoue S, Aoki Y, Kawabata Y, Matsui T, Yamamoto K, Sato H, Yamauchi Y, Yamada S. 2011. Development of inhalable nanocrystalline solid dispersion of tranilast for airway inflammatory diseases. J Pharm Sci 100:622-633.
13. Takatsuka T, Endo T, Jianguo Y, Yuminoki K, Hashimoto N. 2009. Nanosizing of poorly water soluble compounds using rotation/revolution mixer. Chem Pharm Bull (Tokyo) 57(10):1061-1067.
14. Hancock BC, Zografi G. 1997. Characteristics and significance of the amorphous state in pharmaceutical systems. J Pharm Sci 86(1):1-12.
15. Grau MJ, Kayser O, Muller RH. 2000. Nanosuspensions of poorly soluble drugs-reproducibility of small scale production. Int J Pharm 196(2):155-159.
16. Chiou WL, Riegelman S. 1971. Pharmaceutical applications of solid dispersion systems. J Pharm Sci 60(9):1281-1302.
17. Yada S, Ohya M, Ohuchi Y, Hamaura T, Wakiyama N, Usui F, Kusai A, Yamamoto K. 2003. Solid phase transition of CS-891 enantiotropes during grinding. Int J Pharm 255(1-2):69-79.
18. Crowley KJ, Zografi G. 2002. Cryogenic grinding of indomethacin polymorphs and solvates: Assessment of amorphous phase formation and amorphous phase physical stability. J Pharm Sci 91(2):492-507.
19. Chen J, Montanari AM, Widmer WW. 1997. Two new polymethoxylated flavones, a class of compounds with potential anticancer activity, isolated from cold pressed dancy tangerine peel oil solids. J Agric Food Chem 45:364-368.
20. Friesen DT, Shanker R, Crew M, Smithey DT, Curatolo WJ, Nightingale JA. 2008. Hydroxypropyl methylcellulose acetate succinate-based spray-dried dispersions: An overview. Mol Pharm 5(6):1003-1019.
21. Jinno J, Kamada N, Miyake M, Yamada K, Mukai T, Odomi M, Toguchi H, Liversidge GG, Higaki K, Kimura T. 2006. Effect of particle size reduction on dissolution and oral absorption of a poorly water-soluble drug, cilostazol, in beagle dogs. J Control Release 111(1-2):56-64.
22. Onoue S, Sato H, Ogawa K, Kawabata Y, Mizumoto T, Yuminoki K, Hashimoto N, Yamada S.Improved dissolution and pharmacokinetic behavior of cyclosporine a using high-energy amorphous solid dispersion approach. Int J Pharm in press.
23. Leuner C, Dressman J. 2000. Improving drug solubility for oral delivery using solid dispersions. Eur J Pharm Biopharm 50(1):47-60.
24. Lobenberg R, Amidon GL. 2000. Modern bioavailability, bioequivalence and biopharmaceutics classification system. New scientific approaches to international regulatory standards. Eur J Pharm Biopharm 50(1):3-12.
25. Wu Y, Loper A, Landis E, Hettrick L, Novak L, Lynn K, Chen C, Thompson K, Higgins R, Batra U, Shelukar S, Kwei G, Storey D. 2004. The role of biopharmaceutics in the development of a clinical nanoparticle formulation of MK-0869: A Beagle dog model predicts improved bioavailability and diminished food effect on absorption in human. Int J Pharm 285(1-2):135-146.
26. Ikegawa T, Ushigome F, Koyabu N, Morimoto S, Shoyama Y, Naito M, Tsuruo T, Ohtani H, Sawada Y. 2000. Inhibition of P-glycoprotein by orange juice components, polymethoxyflavones in adriamycin-resistant human myelogenous leukemia (K562/ADM) cells. Cancer Lett 160(1):21-28.