Fabrication, solid state characterization and bioavailability assessment of stable binary amorphous phases of Ritonavir with Quercetin

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 89, Issue , 2015, Pages 329-338

  Dengale, Swapnil J ^a   Hussen, Syed Sajjad ^a   Krishna, B S M ^a   Musmade, Prashant B ^a   Gautham Shenoy, G ^a   Bhat, Krishnamurthy ^a  

^a MANIPAL COLLEGE OF PHARMACEUTICAL SCIENCES   (India)

Author keywords

Binary amorphous forms; Bioavailability; Quercetin; Ritonavir; Solid state characterization; Solubility

Indexed keywords

QUERCETIN; RITONAVIR; SOLVENT; GLASS;

AREA UNDER THE CURVE; ARTICLE; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG HALF LIFE; DRUG PENETRATION; DRUG SOLUBILITY; DRUG STABILITY; EVAPORATION; GLASS TRANSITION TEMPERATURE; INFRARED SPECTROSCOPY; MAXIMUM PLASMA CONCENTRATION; SOLID STATE; TEMPERATURE; THERMODYNAMICS; TIME TO MAXIMUM PLASMA CONCENTRATION; X RAY DIFFRACTION; ANIMAL; BIOAVAILABILITY; CHEMISTRY; KINETICS; METABOLISM; ORAL DRUG ADMINISTRATION; PROCEDURES; RAT; SOLUBILITY; WISTAR RAT;

ADMINISTRATION, ORAL; ANIMALS; BIOLOGICAL AVAILABILITY; CALORIMETRY, DIFFERENTIAL SCANNING; CRYSTALLIZATION; DRUG STABILITY; GLASS; KINETICS; QUERCETIN; RATS; RATS, WISTAR; RITONAVIR; SOLUBILITY; SOLVENTS; TEMPERATURE; X-RAY DIFFRACTION;

EID: 84920771419     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2014.12.025     Document Type: Article

References (36)

1. P. Sharma, S. Garg, Pure drug and polymer based nanotechnologies for the improved solubility, stability, bioavailability and targeting of anti-HIV drugs, Adv. Drug Delivery Rev. 62 (2010) 491-502.
2. M. Lindenberg, S. Kopp, J.B. Dressman, Classification of orally administered drugs on the World Health Organization Model list of Essential Medicines according to the biopharmaceutics classification system, Eur. J. Pharm. Biopharm. 58 (2004) 265-278.
3. L. Dickinson, S. Khoo, D. Back, Pharmacokinetics and drug-drug interactions of antiretrovirals: an update, Antiviral Res. 85 (2010) 176-189.
4. S.M. Pathak, P. Musmade, S. Dengle, A. Karthik, K. Bhat, N. Udupa, Enhanced oral absorption of Saquinavir with methyl-beta-cyclodextrin-preparation and in vitro and in vivo evaluation, Eur. J. Pharm. Sci. 41 (2010) 440-451.
5. S. Sinha, M. Ali, S. Baboota, A. Ahuja, A. Kumar, J. Ali, Solid dispersion as an approach for bioavailability enhancement of poorly water-soluble drug Ritonavir, AAPS PharmSciTech 11 (2010) 518-527.
6. J.F. Denissen, B.A. Grabowski, M.K. Johnson, A.M. Buko, D.J. Kempf, S.B. Thomas, B.W. Surber, Metabolism and disposition of the HIV-1 protease inhibitor Ritonavir (ABT-538) in rats, dogs, and humans, Drug Metab. Dispos. 25 (1997) 489-501.
7. M.D. Perloff, L.L. Von Moltke, J.E. Marchand, D.J. Greenblatt, Ritonavir induces P-glycoprotein expression, multidrug resistance-associated protein (MRP1) expression, and drug transporter-mediated activity in a human intestinal cell line, J. Pharm. Sci. 90 (2001) 1829-1837.
8. D. Law, E.A. Schmitt, K.C. Marsh, E.A. Everitt, W. Wang, J.J. Fort, S.L. Krill, Y. Qiu, Ritonavir-PEG 8000 amorphous solid dispersions: in vitro and in vivo evaluations, J. Pharm. Sci. 93 (2004) 563-570.
9. D. Pal, D. Kwatra, M. Minocha, D.K. Paturi, B. Budda, A.K. Mitra, Efflux transporters-and cytochrome P-450-mediated interactions between drugs of abuse and antiretrovirals, Life Sci. 88 (2011) 959-971.
10. Y.-B. Yu, H. Miyashiro, N. Nakamura, M. Hattori, J.C. Park, Effects of triterpenoids and flavonoids isolated from Alnus firma on HIV-1 viral enzymes, Arch. Pharmacal Res. 30 (2007) 820-826.
11. G. Spedding, A. Ratty, E. Middleton Jr, Inhibition of reverse transcriptases by flavonoids, Antiviral Res. 12 (1989) 99-110.
12. M.A. Nguyen, P. Staubach, S. Wolffram, P. Langguth, Effect of single-dose and short-term administration of Quercetin on the pharmacokinetics of talinolol in humans - implications for the evaluation of transporter-mediated flavonoid-drug interactions, Eur. J. Pharm. Sci. 61 (2014) 54-60.
13. S.-L. Hsiu, Y.-C. Hou, Y.-H. Wang, C.-W. Tsao, S.-F. Su, P.-D.L. Chao, Quercetin significantly decreased cyclosporin oral bioavailability in pigs and rats, Life Sci. 72 (2002) 227-235.
14. J. Křížková, K. Burdová, M. Stiborová, V. Křen, P. Hodek, The effects of selected flavonoids on cytochromes P450 in rat liver and small intestine, Interdiscip. Toxicol. 2 (2009) 201-204.
15. W. Brand, M.E. Schutte, G. Williamson, J.J. van Zanden, N.H. Cnubben, J.P. Groten, P.J. van Bladeren, I.M. Rietjens, Flavonoid-mediated inhibition of intestinal ABC transporters may affect the oral bioavailability of drugs, foodborne toxic compounds and bioactive ingredients, Biomed. Pharmacother. 60 (2006) 508-519.
16. C.-P. Yu, P.-P. Wu, Y.-C. Hou, S.-P. Lin, S.-Y. Tsai, C.-T. Chen, P.-D.L. Chao, Quercetin and rutin reduced the bioavailability of cyclosporine from Neoral, an immunosuppressant, through activating P-glycoprotein and CYP 3A4, J. Agric. Food Chem. 59 (2011) 4644-4648.
17. M. Kakran, N. Sahoo, L. Li, Dissolution enhancement of Quercetin through nanofabrication, complexation, and solid dispersion, Colloids Surf., B 88 (2011) 121-130.
18. M. Kakran, R. Shegokar, N.G. Sahoo, L. Al Shaal, L. Li, R.H. Müller, Fabrication of Quercetin nanocrystals: comparison of different methods, Eur. J. Pharm. Biopharm. 80 (2012) 113-121.
19. L. Gao, G. Liu, X. Wang, F. Liu, Y. Xu, J. Ma, Preparation of a chemically stable Quercetin formulation using nanosuspension technology, Int. J. Pharm. 404 (2011) 231-237.
20. R. Laitinen, K. Löbmann, C.J. Strachan, H. Grohganz, T. Rades, Emerging trends in the stabilization of amorphous drugs, Int. J. Pharm. 453 (2013) 65-79.
21. S. Yamamura, M. Momose, K. Takahashi, S. Nagatani, Solid-state interaction between cimetidine and naproxen, Drug Stab. 50 (1996) 173-178.
22. S. Yamamura, H. Gotoh, Y. Sakamoto, Y. Momose, Physicochemical properties of amorphous precipitates of cimetidine-indomethacin binary system, Eur. J. Pharm. Biopharm. 49 (2000) 259-265.
23. S. Yamamura, H. Gotoh, Y. Sakamoto, Y. Momose, Physicochemical properties of amorphous salt of cimetidine and diflunisal system, Int. J. Pharm. 241 (2002) 213-221.
24. M. Allesø, N. Chieng, S. Rehder, J. Rantanen, T. Rades, J. Aaltonen, Enhanced dissolution rate and synchronized release of drugs in binary systems through formulation: amorphous naproxen-cimetidine mixtures prepared by mechanical activation, J. Controlled Release 136 (2009) 45-53.
25. K. Löbmann, C. Strachan, H. Grohganz, T. Rades, O. Korhonen, R. Laitinen, Coamorphous simvastatin and glipizide combinations show improved physical stability without evidence of intermolecular interactions, Eur. J. Pharm. Biopharm. 81 (2012) 159-169.
26. N. Chieng, J. Aaltonen, D. Saville, T. Rades, Physical characterization and stability of amorphous indomethacin and ranitidine hydrochloride binary systems prepared by mechanical activation, Eur. J. Pharm. Biopharm. 71 (2009) 47-54.
27. Y.B. Pawar, G. Shete, D. Popat, A.K. Bansal, Phase behavior and oral bioavailability of amorphous Curcumin, Eur. J. Pharm. Sci. 47 (2012) 56-64.
28. S.L. Shamblin, X. Tang, L. Chang, B.C. Hancock, M.J. Pikal, Characterization of the time scales of molecular motion in pharmaceutically important glasses, J. Phys. Chem. B 103 (1999) 4113-4121.
29. S.J. Dengale, O.P. Ranjan, S.S. Hussen, B. Krishna, P.B. Musmade, G. Gautham Shenoy, K. Bhat, Preparation and characterization of Co-amorphous Ritonavir-Indomethacin systems by solvent evaporation technique: improved dissolution behavior and physical stability without evidence of intermolecular interactions, Eur. J. Pharm. Sci. (2014).
30. L. Yu, Amorphous pharmaceutical solids: preparation, characterization and stabilization, Adv. Drug Delivery Rev. 48 (2001) 27-42.
31. D.Q. Craig, P.G. Royall, V.L. Kett, M.L. Hopton, The relevance of the amorphous state to pharmaceutical dosage forms: glassy drugs and freeze dried systems, Int. J. Pharm. 179 (1999) 179-207.
32. P.J. Marsac, T. Li, L.S. Taylor, Estimation of drug-polymer miscibility and solubility in amorphous solid dispersions using experimentally determined interaction parameters, Pharm. Res. 26 (2009) 139-151.
33. F. Qian, J. Huang, M.A. Hussain, Drug-polymer solubility and miscibility: stability consideration and practical challenges in amorphous solid dispersion development, J. Pharm. Sci. 99 (2010) 2941-2947.
34. D.E. Alonzo, G.G. Zhang, D. Zhou, Y. Gao, L.S. Taylor, Understanding the behavior of amorphous pharmaceutical systems during dissolution, Pharm. Res. 27 (2010) 608-618.
35. K. Lóbmann, R. Laitinen, H. Grohganz, K.C. Gordon, C. Strachan, T. Rades, Coamorphous drug systems: enhanced physical stability and dissolution rate of indomethacin and naproxen, Mol. Pharm. 8 (2011) 1919-1928.
36. C.-Y. Wu, L.Z. Benet, Predicting drug disposition via application of BCS: transport/absorption/elimination interplay and development of a biopharmaceutics drug disposition classification system, Pharm. Res. 22 (2005) 11-23.