Development of an oral rutin nanocrystal formulation

International Journal of Pharmaceutics

Volumn 370, Issue 1-2, 2009, Pages 202-209

  Mauludin, Rachmat ^a   Müller, Rainer H ^a   Keck, Cornelia M ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Dissolution behavior; Lyophilization; Nanocrystals; Re dispersion; Rutin; Rutin nanocrystal loaded tablet

Indexed keywords

RUTOSIDE;

ARTICLE; BIOAVAILABILITY; CONTROLLED STUDY; CRYSTAL; DISSOLUTION; DRUG FORMULATION; DRUG RELEASE; FREEZE DRYING; LASER DIFFRACTION; MICROSCOPY; MORPHOLOGY; PARTICLE SIZE; PHOTON CORRELATION SPECTROSCOPY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; SOLUBILITY; TABLET COMPRESSION; TABLET FORMULATION;

CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; DRUG COMPOUNDING; DRUG DELIVERY SYSTEMS; FREEZE DRYING; KINETICS; NANOPARTICLES; PARTICLE SIZE; RUTIN; SOLUBILITY; TABLETS; TECHNOLOGY, PHARMACEUTICAL;

EID: 61349095957     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2008.11.029     Document Type: Article

References (56)

1. Auweter, H., Bohn, H., Heger, R., Horn, D., Siegel, B., Siemensmeyer, K., 2002. Precipitated water-insoluble colorants in colloid disperse form. United States Patent 6,494,924.
2. Buckton G., and Beezer A.E. The relationship between particle size and solubility. Int. J. Pharm. 82 (1992) R7-R10
3. Busignies V., Leclerc B., Porion P., Evesque P., Couarraze G., and Tchoreloff P. Compaction behaviour and new predictive approach to the compressibility of binary mixtures of pharmaceutical excipients. Eur. J. Pharm. Biopharm. 64 (2006) 66-74
4. Calabro M.L., Tommasini S., Donato P., Stancanelli R., Raneri D., Catania S., Costa C., Villari V., Ficarra P., and Ficarra R. The rutin/beta-cyclodextrin interactions in fully aqueous solution: spectroscopic studies and biological assays. J. Pharm. Biomed. Anal. 36 (2005) 1019-1027
5. Chen S., Gong J., Liu F., and Mohammed U. Naturally occurring polyphenolic antioxidants modulate IgE-mediated mast cell activation. Immunology 100 (2000) 471-480
6. Day A.J., and Williamson G. Biomarkers for exposure to dietary flavonoids: a review of the current evidence for identification of quercetin glycosides in plasma. Br. J. Nutr. (2001) S105-110
7. Deschner E.E., Ruperto J., Wong G., and Newmark H.L. Quercetin and rutin as inhibitors of azoxymethanol-induced colonic neoplasia. Carcinogenesis 12 (1991) 1193-1196
8. Fichtinger, A., 2004. Untersuchungen zur Stabilität,Lösungsgeschwindigkeit und Sättigungslöslichkeit von Cyclosporin-Nanosuspensionen. Diplom, Freie Universität, Berlin.
9. Hecq J., Deleers M., Fanara D., Vranckx H., and Amighi K. Preparation and characterization of nanocrystals for solubility and dissolution rate enhancement of nifedipine. Int. J. Pharm. 299 (2005) 167-177
10. Hintz R.J., and Johnson K.C. The effect of particle size distribution on dissolution rate and oral absorption. Int. J. Pharm. 51 (1989) 9-17
11. Hodnick W.F., Kung F.S., Roettger W.J., Bohmont C.W., and Pardini R.S. Inhibition of mitochondrial respiration and production of toxic oxygen radicals by flavonoids. A structure-activity study. Biochem. Pharmacol. 35 (1986) 2345-2357
12. Hu J., Johnston K.P., and Williams III R.O. Nanoparticle engineering processes for enhancing the dissolution rates of poorly water soluble drugs. Drug Dev. Ind. Pharm. 30 (2004) 233-245
13. Ihme N., Kiesewetter H., Jung F., Hoffmann K.H., Birk A., Muller A., and Grutzner K.I. Leg oedema protection from a buckwheat herb tea in patients with chronic venous insufficiency: a single-centre, randomised, double-blind, placebo-controlled clinical trial. Eur. J. Clin. Pharmacol. 50 (1996) 443-447
14. Jacobs C., Kayser O., and Müller R.H. Production and characterisation of mucoadhesive nanosuspensions for the formulation of bupravaquone. Int. J. Pharm. 214 (2001) 3-7
15. Janbaz K.H., Saeed S.A., and Gilani A.H. Protective effect of rutin on paracetamol- and CCl4-induced hepatotoxicity in rodents. Fitoterapia 73 (2002) 557-563
16. Jinno J., Kamada N., Miyake M., Yamada K., Mukai T., Odomi M., Toguchi H., Liversidge G.G., Higaki K., and Kimura T. Effect of particle size reduction on dissolution and oral absorption of a poorly water-soluble drug, cilostazol, in beagle dogs. J. Control. Release 111 (2006) 56-64
17. Keck C., Fichtinger A., Viernstein H., and Müller R.H. Oral Drug Nanocrystals - Effect Of Potential Aggregation On Bioavailability. Annual Meeting of Pharmaceutical Scientists (AAPS). Baltimore (2004) 2746
18. Keck C.M., and Müller R.H. Drug nanocrystals of poorly soluble drugs produced by high pressure homogenisation. Eur. J. Pharm. Biopharm. 62 (2006) 3-16
19. Keck, C.M., Müller, R.H., in press. smartCrystals-Review of the Second Generation of Drug Nanocrystals. In: Torchilin, V.P. (Ed.), Nanoparticlulates as Drug Carriers, Imperial College Press, London.
20. Kipp, J.E., Wong, J.C.T., Doty, M.J., Rebbeck, C.L., 2003. Microprecipitation method for preparing submicron suspensions. United States Patent 6,607,784.
21. List, M., Sucker, H., 1988. Pharmaceutical colloidal hydrosols for injection. GB Patent 2,200,048.
22. Liversidge G.G., and Conzentino P. Drug particle size reduction for decreasing gastric irritancy and enhancing absorption of naproxen in rats. Int. J. Pharm. 125 (1995) 309-313
23. Liversidge G.G., and Cundy K.C. Particle size reduction for improvement of oral bioavailability of hydrophobic drugs: I. Absolute oral bioavailability of nanocrystalline danazol in beagle dogs. Int. J. Pharm. 125 (1995) 91-97
24. Liversidge, G.G., Cundy, K.C., Bishop, J.F., Czekai, D.A., 1992. Surface modified drug nanoparticles. United States Patent 5,145,684.
25. Liversidge, G.G., Phillips, C.P., Cundy, K.C., 1994. Method to reduce particle size growth during lyophilization. United States Patent 5,302,401.
26. Mata R., Rojas A., Acevedo L., Estrada S., Calzada F., Rojas I., Bye R., and Linares E. Smooth muscle relaxing flavonoids and terpenoids from Conyza filaginoides. Planta Med. 63 (1997) 31-35
27. Mauludin, R., 2008. Nanosuspensions of poorly soluble drugs for oral administration. PhD Thesis, Free University, Berlin.
28. Merisko-Liversidge E., Liversidge G.G., and Cooper E.R. Nanosizing: a formulation approach for poorly-water-soluble compounds. Eur. J. Pharm. Sci. 18 (2003) 113-120
29. Miyake K., Arima H., Hirayama F., Yamamoto M., Horikawa T., Sumiyoshi H., Noda S., and Uekama K. Improvement of solubility and oral bioavailability of rutin by complexation with 2-hydroxypropyl-beta-cyclodextrin. Pharm. Dev. Technol. 5 (2000) 399-407
30. Müller, R.H., 1998. Nanosuspensionen - eine neue Formulierung für schwerlösliche Arzneistoffe. In: Müller, R.H., Hildebrand, G.E. (Eds.), Pharmazeutische Technologie: Moderne Arzneiformen Wissenschaftliche Verlagsgesellschaft, Stuttgart, pp. 393-400.
31. Müller R.H., and Akkar A. Drug nanocrystals of poorly soluble drugs. In: Nalwa H.S. (Ed). Encyclopedia of Nanoscience and Nanotechnology (2004), American Scientific Publishers 627-638
32. Müller, R.H., Becker, R., Kruss, B., Peters, K., 1999a. Pharmaceutical nanosuspensions for medicament administration as systems with increased saturation solubility and rate of solution. United States Patent 5,858,410.
33. Müller, R.H., Benita, S., Böhm, B., 1998. Emulsions and Nanosuspensions for the Formulation of Poorly Soluble Drugs, medpharm, Stuttgart.
34. Müller R.H., Böhm B.H.L., and Grau M.J. Nanosuspensionen - Formulierungen für schwerlösliche Arzneistoffe mit geringer Bioverfügbarkeit: II. Stabilität, biopharmazeutische Aspekte, mögliche Arzneiformen und Zulassungsfragen. Pharm. Ind. 61 (1999) 175-178
35. Müller R.H., Böhm B.H.L., and Grau M.J. Nanosuspensions-a formulation approach for poorly soluble and poorly bioavailable drugs. In: Wise D.L. (Ed). Handbook of Pharmaceutical Controlled Release (2000), Marcel Dekker, New York 345-357
36. Müller R.H., Jacobs C., and Kayser O. Nanosuspensions as particulate drug formulations in therapy: rationale for development and what we can expect for the future. Adv. Drug Deliv. Rev. 47 (2001) 3-19
37. Müller R.H., Jacobs C., and Kayser O. DissoCubes-a novel formulation for poorly soluble and poorly bioavailable drugs. In: Rathbone M.J., Hadgraft J., et al. (Eds). Modified-Release Drug Delivery Systems (2003), Marcel Dekker 135-149
38. Müller R.H., Jacobs C., and Kayser O. Nanosuspensions for the formulation of poorly soluble drugs. In: Nielloud F., and Marti-Mestres G. (Eds). Pharmaceutical Emulsions and Suspensions (2000), Marcel Dekker 383-407
39. Müller R.H., and Keck C.M. Improvement of Delivery & Solubility of Poorly Soluble Drugs by Nanonisation (2007), LTS Academy, Petersberg pp. 12-17
40. Müller, R.H., Mäder, K., Krause, K., 2000c. Verfahren zur schonenden Herstellung von hochfeinen Micro-/Nanopartikeln. PCT Application PCT/EP00/06535.
41. Müller R.H., Möschwitzer J., and Bushrab F.N. Manufacturing of nanoparticles by milling and homogenisation techniques. In: Gupta R.B., and Kompella U.B. (Eds). Nanoparticle Technology for Drug Delivery (2006), Tayler & Francis Group, New York 21-52
42. Munoz N., Ferrero C., Munoz-Ruiz A., Velasco M.V., and Jimenez-Castellanos M.R. Effect of Explotab on the tabletability of a poorly soluble drug. Drug Dev. Ind. Pharm. 24 (1998) 785-791
43. Noyes A.A., and Whitney W.R. The rate of solution of solid substances in their own solutions. J. Am. Chem. Soc. 19 (1897) 930-934
44. Panasiak W., Wleklik M., Oraczewska A., and Luczak M. Influence of flavonoids on combined experimental infections with EMC virus and Staphylococcus aureus in mice. Acta Microbiol. Pol. 38 (1989) 185-188
45. Park S.Y., Bok S.H., Jeon S.M., Park Y.B., Lee S.J., Jeong T.S., and Choi M.S. Effect of rutin and tannic acid supplements on cholesterol metabolism in rats. Nutr. Res. 22 (2002) 283-295
46. Petersen, R.D., 2006. Nanocrystals for use in topical formulations and method of production thereof. PCT/EP2007/009943.
47. Public Health Service, 2000. 1999 USPHS/IDSA Guidelines for the Prevention of Opportunistic Infections in Persons Infected with HIV: Part II. Prevention of the first episode of disease. Am Fam Physician, 61, 441-442, 445-449, 453-444 passim.
48. Rao M.Y., Kumar M., and Apte S. Formulation of nanosuspensions of albendazole for oral administration. Curr. Nanosci. 4 (2008) 53-58
49. Rutin, 2008. Physicians' Desk Reference, Thomson Healthcare. www.pdrhealth.com.
50. Schöler N., Krause K., Kayser O., Müller R.H., Hartwig H., Hahn H., and Liesenfeld O. Atovaquone nanosuspensions show excellent therapeutic effect in a new murine model of reactivated toxoplasmosis. Antimicrob. Agents Chemother. (2001) 1771-1779
51. Sucker, H., Gassmann, P., 1994. Improvements in pharmaceutical compositions. European Patent 0,580,690.
52. Takagi, H., Kajiyama, A., Yanagisawa, M., 2007. Rapidly disintegrable pharmaceutical composition. United States Patent 7,189,415.
53. Takano R., Furumoto K., Shiraki K., Takata N., Hayashi Y., Aso Y., and Yamashita S. Rate-limiting steps of oral absorption for poorly water-soluble drugs in dogs; prediction from a miniscale dissolution test and a physiologically-based computer simulation. Pharm. Res. (2008)
54. Webster R.P., Gawde M.D., and Bhattacharya R.K. Protective effect of rutin, a flavonol glycoside, on the carcinogen-induced DNA damage and repair enzymes in rats. Cancer Lett. 109 (1996) 185-191
55. Weder, H.G., Van Hoogevest, P., 1998. Nanosuspensions for intravenous administration. United States Patent 5,726,164.
56. Wu T.H., Yen F.L., Lin L.T., Tsai T.R., Lin C.C., and Cham T.M. Preparation, physicochemical characterization, and antioxidant effects of quercetin nanoparticles. Int. J. Pharm. 346 (2008) 160-168