Supersaturation-nucleation behavior of poorly soluble drugs and its impact on the oral absorption of drugs in thermodynamically high-energy forms

Journal of Pharmaceutical Sciences

Volumn 101, Issue 1, 2012, Pages 214-222

  Ozaki, Shunsuke ^a   Minamisono, Takuma ^a   Yamashita, Taro ^a   Kato, Takashi ^a   Kushida, Ikuo ^a  

^a EISAI CO LTD   (Japan)

Author keywords

High energy form; In vitro in vivo correlation; Nucleation; Oral absorption; Precipitation; Solubility; Supersaturation

Indexed keywords

DRUG SOLVENT; ERLOTINIB; ITRACONAZOLE; TROGLITAZONE; VEMURAFENIB;

ARTICLE; CONTROLLED STUDY; DRUG ABSORPTION; DRUG MONITORING; DRUG SOLUBILITY; DRUG STABILITY; IN VITRO STUDY; THERMODYNAMICS; ULTRAVIOLET RADIATION;

EID: 82255162693     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22760     Document Type: Article

References (34)

1. Yu LX. 1999. An integrated model for determining causes of poor oral drug absorption. Pharm Res 16:1883-1887.
2. Takano R, Furumoto K, Shiraki K, Takata N, Hayashi Y, Aso Y, Yamashita S. 2008. 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 25:2334-2344.
3. Leuner C, Dressman JB. 2000. Improving drug solubility for oral delivery using solid dispersions. Eur J Pharm Biopharm 50:47-60.
4. Yamashita K, Nakate T, Okimoto K, Ohike A, Tokunaga Y, Ibuki R, Higaki K, Kimura T. 2003. Establishment of new preparation method for solid dispersion formulation of tacrolimus. Int J Pharm 267:79-91.
5. Serajuddin ATM. 2007. Salt formation to improve drug solubility. Adv Drug Deliv Rev 59:603-616.
6. Schultheiss N, Newman A. 2009. Pharmaceutical cocrystals and their physicochemical properties. Cryst Growth Des 9:2590-2967.
7. Kushida I, Ichikawa M, Asakawa N. 2002. Improvement of dissolution and oral absorption of ER-34122, a poorly water-soluble dual 5-lipoxygenase/cyclooxygenase inhibitor with anti-inflammatory activity by preparing solid dispersion. J Pharm Sci 91:258-266.
8. Brouwers J, Brewster ME, Augustijns P. 2009. Supersaturating drug delivery systems: The answer to solubility-limited oral bioavailability? J Pharm Sci 98:2549-2572.
9. Takano R, Takata N, Saito R, Furumoto K, Higo S, Hayashi Y, Machida M, Aso Y, Yamashita S. 2010. Quantitative analysis of the effect of supersaturation on in vivo drug absorption. Mol Pharm 7:1431-1440.
10. Janssens S, Nagels S, Armas HN, D'Autry W, Schepdael AV, Mooter GV. 2008. Formulation and characterization of ternary solid dispersions made up of Itraconazole and two excipients, TPGS. 1000 and PVPVA 64, that were selected based on a supersaturation screening study. Eur J Pharm Biopharm 69:158-166.
11. Tarsa PB, Towler CS, Woollam G, Berghausen J. 1991. The influence of aqueous content in small scale salt screening-Improving hit rate for weakly basic, low solubility drugs. Eur J Pharm Sci 41:21-30.
12. Kojima T, Tsutsumi S, Yamamoto K, Ikeda Y, Moriwaki T. 2010. High-throughput cocrystal slurry screening by use of in situ Raman microscopy and multi-well plate. Int J Pharm 399:52-59.
13. Sugano K. 2009. Introduction to computational oral absorption simulation. Expert Opin Drug Metab Toxicol 5:252-293.
14. Murdande SB, Pikal MJ, Shanker RM, Bogner RH. 2010. Solubility advantage of amorphous pharmaceuticals: I. A thermodynamic analysis. J Pharm Sci 99:1254-1264.
15. Dalvi SV, Dave RN. 2010. Analysis of nucleation kinetics of poorly water-soluble drugs in presence of ultrasound and hydroxypropyl methyl cellulose during antisolvent precipitation. Int J Pharm 387:172-179.
16. Bevernage J, Brouwers J, Clarysse S, Vertzoni M, Tack J, Annaert P, Augustijns P. 2010. Drug supersaturation in simulated and human intestinal fluids representing different nutritional states. J Pharm Sci 99:4523-4534.
17. Furukawa S, Zhao C, Ohki Y. 2010. Methodology for phase selection of a weak basic drug candidate, utilizing kinetic solubility profiles in bio-relevant media. Eur J Pharm Biopharm 74(2):298-303.
18. 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 94:199-208.
19. 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 56:43-51.
20. Sugano K. 2009. A simulation of oral absorption using classical nucleation theory. Int J Pharm 378:142-145.
21. Sugano K, Okazaki A, Sugimoto S, Tavornvipas S, Omura A, Mano T. 2010. Solubility and dissolution profile assessment in drug discovery. Drug Metab Pharmacokinet 22:225-254.
22. Gu CH, Young V Jr., Grant DJW. 2001. Polymorph screening: Influence of solvents on the rate of solvent-mediated polymorphic transformation. J Pharm Sci 90:1878-1890.
23. Bernardo A, Calmanovici CE, Miranda EA. 2003. Induction time as an instrument to enhance comprehension of protein crystallization. Cryst Growth Des 4:799-805.
24. Kuldipkumar A, Kwon GS, Zhang GGZ. 2007. Determining the growth mechanism of tolazamide by induction time measurement. Cryst Growth Des 7:234-242.
25. Cao S, Zhang Y, Zhang Y. 2010. Nucleation and morphology of monosodium aluminate hydrate from concentrated sodium aluminate solutions. Cryst Growth Des 10:1605-1610.
26. Nicolaides E, Symillides M, Dressman JB, Reppas C. 2001. Biorelevant dissolution testing to predict the plasma profile of lipophilic drugs after oral administration. Pharm Res 18:380-388.
27. Guzman HR, Tawa M, Zhang Z, Ratanabanangkoon P, Shaw P, Gardner CR, Chen H, Moreau JP, Almarsson O, Remenar JF. 2007. Combined use of crystalline salt forms and precipitation inhibitors to improve oral absorption of celecoxib from solid oral formulations. J Pharm Sci 96:2686-2702.
28. Hasegawa S, Furuyama N, Yada S, Hamaura T, Kusai A, Yonemochi E, Terada K. 2007. Effect of physical properties of troglitazone crystal on the molecular interaction with PVP during heating. Int J Pharm 336:82-89.
29. Bollag G, Hirth P, Tsai J, Zhang J, Ibrahim PN, Cho H, Spevak W, Zhang C, Zhang Y, Habets G, Burton EA, Wong B, Tsang G, West BL, Powell B, Shellooe R, Marimuthu A, Nguyen H, Zhang KYJ, Artis DR, Schlessinger J, Su F, Higgins B, Iyer R, D'Andrea K, Koehler A, Stumm M, Lin PS, Lee RJ, Grippo J, Puzanov I, Kim KB, Ribas A, McArthur GA, Sosman JA, Chapman PB, Flaherty KT, Xu X, Nathanson KL, Nolop K. 2010. Clinical efficacy of a RAF inhibitor needs broad target blockade in BRAF-mutant melanoma. Nature 467:596-599.
30. Matteucci ME, Miller MA, Williams RO 3rd, Johnston KP. 2008. Highly supersaturated solutions of amorphous drugs approaching predictions from configurational thermodynamic properties. J Phys Chem B 112:16675-16681.
31. Takano R, Sugano K, Higashida A, Hayashi Y, Machida M, Aso Y, Yamashita S. 2006. Oral absorption of poorly water-soluble drugs: Computer simulation of fraction absorbed in humans from a miniscale dissolution test. Pharm Res 23:1144-1156.
32. Flaherty KT, Puzanov I, Kim KB, Ribas A, McArthur GA, Sosman JA, O'Dwyer PJ, Lee RJ, Grippo JF, Nolop K, Chapman PB. 2010. Inhibition of mutated, activated BRAF in metastatic melanoma. N Engl J Med 363:809-819.
33. Sugano K. 2010. Computational oral absorption simulation of free base drugs. Int J Pharm 398:73-82.
34. Sugano K. 2011. Fraction of a dose absorbed estimation for structurally diverse low solubility compounds. Int J Pharm 405:79-89.