Toward an improved understanding of the precipitation behavior of weakly basic drugs from oral lipid-based formulations

Journal of Pharmaceutical Sciences

Volumn 103, Issue 4, 2014, Pages 1194-1203

  Stillhart, Cordula ^a,b   Dürr, Désirée ^b   Kuentz, Martin ^b  

^a UNIVERSITY OF BASEL   (Switzerland)

^b UNIVERSITY OF APPLIED SCIENCES AND ARTS NORTHWESTERN SWITZERLAND   (Switzerland)

Author keywords

dispersion; formulation; in vitro models; lipid; lipolysis; precipitation; redissolution; solid state; weak bases

Indexed keywords

BASE; CARVEDILOL; LORATADINE;

ARTICLE; DEGRADATION KINETICS; DISPERSION; DRUG FORMULATION; DRUG SOLUBILITY; DRUG STRUCTURE; IN VITRO STUDY; LIPID BASED FORMULATION; LIPOLYSIS; PH; PRECIPITATION; SOLID STATE; X RAY POWDER DIFFRACTION;

DISPERSION; FORMULATION; IN VITRO MODELS; LIPID; LIPOLYSIS; PRECIPITATION; REDISSOLUTION; SOLID-STATE; WEAK BASES;

ANTI-ALLERGIC AGENTS; ANTIHYPERTENSIVE AGENTS; CARBAZOLES; CHEMICAL PRECIPITATION; EXCIPIENTS; LIPIDS; LORATADINE; PROPANOLAMINES; SOLUBILITY; X-RAY DIFFRACTION;

EID: 84896405839     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23892     Document Type: Article

References (36)

1. Hancock BC, Parks M,. 2000. What is the true solubility advantage for amorphous pharmaceuticals? Pharm Res 17 (4): 397-404.
2. Kuentz M, Imanidis G,. 2013. In silico prediction of the solubility advantage for amorphous drugs-Are there property-based rules for drug discovery and early pharmaceutical development? Eur J Pharm Sci 48 (3): 554-562.
3. Anby MU, Williams HD, McIntosh M, Benameur H, Edwards GA, Pouton CW, Porter CJH,. 2012. Lipid digestion as a trigger for supersaturation: Evaluation of the impact of supersaturation stabilization on the in vitro and in vivo performance of self-emulsifying drug delivery systems. Mol Pharmaceutics 9 (7): 2063-2079.
4. Brouwers J, Brewster ME, Augustijns P,. 2009. Supersaturating drug delivery systems: The answer to solubility-limited oral bioavailability? J Pharm Sci 98 (8): 2549-2572.
5. Sanghvi R, Mogalian E, Machatha SG, Narazaki R, Karlage KL, Jain P, Tabibi SE, Glaze E, Myrdal PB, Yalkowsky SH,. 2009. Preformulation and pharmacokinetic studies on Antalarmin: A novel stress inhibitor. J Pharm Sci 98 (1): 205-214.
6. Porter CJH, Trevaskis NL, Charman WN,. 2007. Lipids and lipid-based formulations: Optimizing the oral delivery of lipophilic drugs. Nat Rev Drug Discov 6 (3): 231-248.
7. Williams HD, Trevaskis NL, Charman SA, Shanker RM, Charman WN, Pouton CW, Porter CJH,. 2013. Strategies to address low drug solubility in discovery and development. Pharmacol Rev 65 (1): 315-499.
8. Psachoulias D, Vertzoni M, Goumas K, Kalioras V, Beato S, Butler J, Reppas C,. 2011. Precipitation in and supersaturation of contents of the upper small intestine after administration of two weak bases to fasted adults. Pharm Res 28 (12): 3145-3158.
9. Carlert S, Akesson P, Jerndal G, Lindfors L, Lennernas H, Abrahamsson B,. 2012. in vivo dog intestinal precipitation of mebendazole: A basic BCS class II drug. Mol Pharmaceutics 9 (10): 2903-2911.
10. Kostewicz ES, Wunderlich M, Brauns U, Becker R, Bock T, Dressman JB,. 2004. Predicting the precipitation of poorly soluble weak bases upon entry in the small intestine. J Pharm Pharmacol 56 (1): 43-51.
11. Arnold YE, Imanidis G, Kuentz MT,. 2011. Advancing in-vitro drug precipitation testing: New process monitoring tools and a kinetic nucleation and growth model. J Pharm Pharmacol 63 (3): 333-341.
12. Psachoulias D, Vertzoni M, Butler J, Busby D, Symillides M, Dressman J, Reppas C,. 2012. An in vitro methodology for forecasting luminal concentrations and precipitation of highly permeable lipophilic weak bases in the fasted upper small intestine. Pharm Res 29 (12): 3486-3498.
13. Gu CH, Rao D, Gandhi RB, Hilden J, Raghavan K,. 2005. Using a novel multicompartment dissolution system to predict the effect of gastric pH on the oral absorption of weak bases with poor intrinsic solubility. J Pharm Sci 94 (1): 199-208.
14. Carlert S, Palsson A, Hanisch G, von Corswant C, Nilsson C, Lindfors L, Lennernas H, Abrahamsson B,. 2010. Predicting intestinal precipitation-A case example for a basic BCS class II drug. Pharm Res 27 (10): 2119-2130.
15. Klein S, Buchanan NL, Buchanan CM,. 2012. Miniaturized transfer models to predict the precipitation of poorly soluble weak bases upon entry into the small intestine. AAPS PharmSciTech 13 (4): 1230-1235.
16. Sassene PJ, Knopp MM, Hesselkilde JZ, Koradia V, Larsen A, Rades T, Mullertz A,. 2010. Precipitation of a poorly soluble model drug during in vitro lipolysis: Characterization and dissolution of the precipitate. J Pharm Sci 99 (12): 4982-4991.
17. Thomas N, Holm R, Mullertz A, Rades T,. 2012. in vitro and in vivo performance of novel supersaturated self-nanoemulsifying drug delivery systems (super-SNEDDS). J Control Release 160 (1): 25-32.
18. Thomas N, Holm R, Garmer M, Karlsson JJ, Mullertz A, Rades T,. 2013. Supersaturated self-nanoemulsifying drug delivery systems (super-SNEDDS) enhance the bioavailability of the poorly water-soluble drug simvastatin in dogs. AAPS J 15 (1): 219-227.
19. Williams H, Sassene P, Kleberg K, Calderone M, Igonin A, Jule E, Vertommen J, Blundell R, Benameur H, Müllertz A, Pouton C, Porter CH,. 2013. Toward the establishment of standardized in vitro tests for lipid-based formulations, Part 3: Understanding supersaturation versus precipitation potential during the in vitro digestion of Type I, II, IIIA, IIIB and IV lipid-based formulations. Pharm Res 30 (12): 3059-3076.
20. Hsieh YL, Ilevbare GA, Van Eerdenbrugh B, Box KJ, Sanchez-Felix MV, Taylor LS,. 2012. pH-Induced precipitation behavior of weakly basic compounds: Determination of extent and duration of supersaturation using potentiometric titration and correlation to solid state properties. Pharm Res 29 (10): 2738-2753.
21. Sek L, Porter CJH, Charman WN,. 2001. Characterisation and quantification of medium chain and long chain triglycerides and their in vitro digestion products, by HPTLC coupled with in situ densitometric analysis. J Pharm Biomed 25 (3-4): 651-661.
22. Stillhart C, Imanidis G, Kuentz M,. 2013. Insights into drug precipitation kinetics during in vitro digestion of a lipid-based drug delivery system using in-line Raman spectroscopy and mathematical modeling. Pharm Res 30 (12): 3114-3130.
23. Cuine JF, McEvoy CL, Charman WN, Pouton CW, Edwards GA, Benameur H, Porter CJH,. 2008. Evaluation of the impact of surfactant digestion on the bioavailability of danazol after oral administration of lipidic self-emulsifying formulations to dogs. J Pharm Sci 97 (2): 995-1012.
24. Garner CW,. 1980. Boronic acid inhibitors of porcine pancreatic lipase. J Biol Chem 255 (11): 5064-5068.
25. Williams HD, Sassene P, Kleberg K, Bakala-N'Goma JC, Calderone M, Jannin V, Igonin A, Partheil A, Marchaud D, Jule E, Vertommen J, Maio M, Blundell R, Benameur H, Carriere F, Mullertz A, Porter CJH, Pouton CW,. 2012. Toward the establishment of standardized in vitro tests for lipid-based formulations, part 1: Method parameterization and comparison of in vitro digestion profiles across a range of representative formulations. J Pharm Sci 101 (9): 3360-3380.
26. Stillhart C, Cavegn M, Kuentz M,. 2013. Study of drug supersaturation for rational early formulation screening of surfactant/co-solvent drug delivery systems. J Pharm Pharmacol 65 (2): 181-192.
27. Kostewicz ES, Brauns U, Becker R, Dressman JB,. 2002. Forecasting the oral absorption behavior of poorly soluble weak bases using solubility and dissolution studies in biorelevant media. Pharm Res 19 (3): 345-349.
28. Tung H-H, Paul EL, Midler M, McCauley JA,. 2009. Properties. In Crystallization of organic compounds: An industrial perspective;, Tung H-H, Ed. Hoboken New Jersey: John Wiley & Sons.
29. Bevernage J, Forier T, Brouwers J, Tack J, Annaert P, Augustijns P,. 2011. Excipient-mediated supersaturation stabilization in human intestinal fluids. Mol Pharmaceutics 8 (2): 564-570.
30. Li Y, McClements DJ,. 2010. New mathematical model for interpreting pH-stat digestion profiles: Impact of lipid droplet characteristics on in vitro digestibility. J Agric Food Chem 58 (13): 8085-8092.
31. Yeap YY, Trevaskis NL, Quach T, Tso P, Charman WN, Porter CJH,. 2013. Intestinal bile secretion promotes drug absorption from lipid colloidal phases via induction of supersaturation. Mol Pharmaceutics 10 (5): 1874-1889.
32. Lucas ML, Schneider W, Haberich FJ, Blair JA,. 1975. Direct measurement by pH-microelectrode of the pH microclimate in rat proximal jejunum. Proc R Soc Lond B Biol Sci 192 (1106): 39-48.
33. Shiau YF, Fernandez P, Jackson MJ, McMonagle S,. 1985. Mechanisms maintaining a low-pH microclimate in the intestine. Am J Physiol 248 (6 Pt 1): G608-617.
34. Ikuma M, Hanai H, Kaneko E, Hayashi H, Hoshi T,. 1996. Effects of aging on the microclimate pH of the rat jejunum. Biochim Biophys Acta 1280 (1): 19-26.
35. Larsen AT, Ohlsson AG, Polentarutti B, Barker RA, Phillips AR, Abu-Rmaileh R, Dickinson PA, Abrahamsson B, Ostergaard J, Mullertz A,. 2013. Oral bioavailability of cinnarizine in dogs: Relation to SNEDDS droplet size, drug solubility and in vitro precipitation. Eur J Pharm Sci 48 (1-2): 339-350.
36. Mahlin D, Ponnambalam S, Hockerfelt MH, Bergstrom CAS,. 2011. Toward in silico prediction of glass-forming ability from molecular structure alone: A screening tool in early drug development. Mol Pharmceutics 8 (2): 498-506.