Evaluation of drug supersaturation by thermodynamic and kinetic approaches for the prediction of oral absorbability in amorphous pharmaceuticals

Journal of Pharmaceutical Sciences

Volumn 101, Issue 11, 2012, Pages 4220-4230

  Ozaki, Shunsuke ^a,b   Kushida, Ikuo ^a   Yamashita, Taro ^a   Hasebe, Takashi ^a   Shirai, Osamu ^a   Kano, Kenji ^b  

^a EISAI CO LTD   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Amorphous; Crystallization; In vitro in vivo correlation; Kinetics; Oral absorption; Supersaturation; Thermodynamics

Indexed keywords

DANAZOL; ER 34122; GRISEOFULVIN; ITRACONAZOLE; PROSTAGLANDIN SYNTHASE INHIBITOR; UNCLASSIFIED DRUG; VEMURAFENIB; WATER;

ARTICLE; DRUG ABSORPTION; DRUG FORMULATION; DRUG SCREENING; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; ISOTHERM; KINETICS; PREDICTION; SOLID; SUPERSATURATION; THERMODYNAMICS;

EID: 84866404405     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23306     Document Type: Article

References (32)

1. Leuner C, Dressman JB. 2000. Improving drug solubility for oral delivery using solid dispersions. Eur J Pharm Biopharm 50:47-60.
2. Brouwers J, Brewster ME, Augustijns P. 2009. Supersaturating drug delivery systems: The answer to solubility-limited oral bioavailability? J Pharm Sci 98:2549-2572.
3. Yu LX. 1999. An integrated model for determining causes of poor oral drug absorption. Pharm Res 16:1883-1887.
4. 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.
5. 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.
6. 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.
7. Sugano K. 2009. Introduction to computational oral absorption simulation. Expert Opin Drug Metab Toxicol 5:252-293.
8. Hancock BC, Parks M. 2000. What is the true solubility advantage for amorphous pharmaceuticals? Pharm Res 17:397-404.
9. Matteucci ME, Miller MA, Williams III RO, Johnston KP. 2008. Highly supersaturated solutions of amorphous drugs approaching predictions from configurational thermodynamic properties. J Phys Chem B 112:16675-16681.
10. Murdande SB, Pikal MJ, Shanker RM, Bogner RH. 2010. Solubility advantage of amorphous pharmaceuticals: I. A thermodynamic analysis. J Pharm Sci 99:1254-1264.
11. Murdande SB, Pikal MJ, Shanker RM, Bogner RH. 2010. Solubility advantage of amorphous pharmaceuticals: II. Application of quantitative thermodynamic relationships for prediction of solubility enhancement in structurally diverse insoluble pharmaceuticals. Pharm Res 27:2704-2714.
12. Murdande SB, Pikal MJ, Shanker RM, Bogner RH. 2011. Solubility advantage of amorphous pharmaceuticals: III. Is maximum solubility advantage experimentally attainable and sustainable? J Pharm Sci 100:4349-4356.
13. Ozaki S, Minamisono T, Yamashita T, Kato T, Kushida I. 2012. Supersaturation-nucleation behavior of poorly soluble drugs and its impact on the oral absorption of drugs in thermodynamically high-energy forms. J Pharm Sci 101:214-222.
14. Vaughn JM, McConville JT, Crisp MT, Johnston KP, Williams III RO. 2006. Supersaturation produces high bioavailability of amorphous danazol particles formed by evaporative precipitation into aqueous solution and spray freezing into liquid technologies. Drug Dev Ind Pharm 32:559-567.
15. Zhang S, Kawakami K, Yamamoto M, Masaoka Y, Kataoka M, Yamashita S, Sakuma S. 2011. Coaxial electrospray formulations for improving oral absorption of a poorly water-soluble drug. Mol Pharm 8:807-813.
16. Chiou WL, Riegelman S. 1971. Absorption characteristics of solid dispersed and micronized griseofulvin in man. J Pharm Sci 60:1376-1380.
17. Chiou WL, Riegelman S. 1970. Oral absorption of griseofulvin in dogs: Increased absorption via solid dispersion in polyethylene glycol 6000. J Pharm Sci 59:937-942.
18. Speybroeck MV, Mols R, Mellaerts R, Thi TD, Martens JA, Humbeeck JV, Annaert P, Mooter GV, Augustijns P. 2010. Combined use of ordered mesoporous silica and precipitation inhibitors for improved oral absorption of the poorly soluble weak base itraconazole. Eur J Pharm Biopharm 75:354-365.
19. 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.
20. 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.
21. 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.
22. Sacchetti M. 1998. Thermodynamic analysis of moisture sorption isotherms. J Pharm Sci 87:982-986.
23. Sugano K. 2009. A simulation of oral absorption using classical nucleation theory. Int J Pharm 378:142-145.
24. Bernardo A, Calmanovici CE, Miranda EA. 2003. Induction time as an instrument to enhance comprehension of protein crystallization. Cryst Growth Des 4:799-805.
25. Kuldipkumar A, Kwon GS, Zhang GGZ. 2007. Determining the growth mechanism of tolazamide by induction time measurement. Cryst Growth Des 7:234-242.
26. 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.
27. Gu CH, Young Jr V, Grant DJW. 2001. Polymorph screening: Influence of solvents on the rate of solvent-mediated polymorphic transformation. J Pharm Sci 90:1878-1890.
28. DeSesso JM, Jacobson CF. 2001. Anatomical and physiological parameters affecting gastrointestinal absorption in humans and rats. Food Chem Toxicol 39:209-228.
29. Kararli TT. 1995. Comparison of the gastrointestinal anatomy, physiology, and biochemistry of humans and commonly used laboratory animals. Biopharm Drug Dispos 16:351-380.
30. 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.
31. 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.
32. g. Pharm Res 23:2350-2355.