The twofold advantage of the amorphous form as an oral drug delivery practice for lipophilic compounds: Increased apparent solubility and drug flux through the intestinal membrane

AAPS Journal

Volumn 15, Issue 2, 2013, Pages 347-353

  Dahan, Arik ^a   Beig, Avital ^a   Ioffe Dahan, Viktoriya ^a   Agbaria, Riad ^a   Miller, Jonathan M ^b  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^b ABBOTT LABORATORIES   (United States)

Author keywords

amorphous solid dispersions; intestinal permeability; lipophilic drugs; oral absorption; solubility permeability interplay

Indexed keywords

COPOVIDONE; CYCLODEXTRIN; HYDROXYPROPYLMETHYLCELLULOSE ACETATE SUCCINATE; NIFEDIPINE; POLYMER; POVIDONE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; AQUEOUS SOLUTION; ARTICLE; ARTIFICIAL MEMBRANE; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG ABSORPTION; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG PENETRATION; DRUG SOLUBILITY; DRUG TRANSPORT; IN VITRO STUDY; IN VIVO STUDY; INTESTINE MEMBRANE; INTESTINE MUCOSA PERMEABILITY; INTESTINE PERFUSION; LIPOPHILICITY; MALE; MEMBRANE; MEMBRANE TRANSPORT; NONHUMAN; POWDER; RAT; X RAY DIFFRACTION;

ADMINISTRATION, ORAL; ANIMALS; CALORIMETRY, DIFFERENTIAL SCANNING; CHEMISTRY, PHARMACEUTICAL; CRYSTALLOGRAPHY, X-RAY; DESICCATION; DRUG COMPOUNDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INTESTINAL ABSORPTION; JEJUNUM; MALE; MEMBRANES, ARTIFICIAL; METHYLCELLULOSE; NIFEDIPINE; PERMEABILITY; POVIDONE; POWDER DIFFRACTION; PYRROLIDINES; RATS; RATS, WISTAR; SOLUBILITY; TECHNOLOGY, PHARMACEUTICAL; TIME FACTORS; VINYL COMPOUNDS;

EID: 84877077844     PISSN: 15507416     EISSN: None     Source Type: Journal    
DOI: 10.1208/s12248-012-9445-3     Document Type: Article

References (30)

1. Dahan A, Hoffman A. Rationalizing the selection of oral lipid based drug delivery systems by an in vitro dynamic lipolysis model for improved oral bioavailability of poorly water soluble drugs. J Control Release. 2008;129(1):1-10. doi: 10.1016/j.jconrel.2008.03.021.
2. Gao P, Shi Y. Characterization of supersaturatable formulations for improved absorption of poorly soluble drugs. AAPS J. 2012. doi:10.1208/s12248- 012-9389-7.
3. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev. 2001;46(1-3):3-26. doi: 10.1016/s0169-409x(00)00129-0.
4. Brouwers J, Brewster ME, Augustijns P. Supersaturating drug delivery systems: The answer to solubility-limited oral bioavailability? J Pharm Sci. 2009;98(8):2549-72. doi: 10.1002/jps.21650.
5. Dahan A, Miller J, Amidon G. Prediction of solubility and permeability class membership: provisional BCS classification of the world's top oral drugs. AAPS J. 2009;11(4):740-6. doi: 10.1208/s12248-009-9144-x.
6. Gao Y, Carr RA, Spence JK, Wang WW, Turner TM, Lipari JM, et al. A pH-dilution method for estimation of biorelevant drug solubility along the gastrointestinal tract: Application to physiologically based pharmacokinetic modeling. Mol Pharm. 2010;7(5):1516-26. doi: 10.1021/mp100157s.
7. Beig A, Miller JM, Dahan A. Accounting for the solubility-permeability interplay in oral formulation development for poor water solubility drugs: The effect of PEG-400 on carbamazepine absorption. Eur J Pharm Biopharm. 2012;81:386-91. doi: 10.1016/j.ejpb.2012.02.012.
8. Dahan A, Miller J. The solubility-permeability interplay and its implications in formulation design and development for poorly soluble drugs. AAPS J. 2012;14(2):244-51. doi: 10.1208/s12248-012-9337-6.
9. Dahan A, Miller JM, Hoffman A, Amidon GE, Amidon GL. The solubility-permeability interplay in using cyclodextrins as pharmaceutical solubilizers: mechanistic modeling and application to progesterone. J Pharm Sci. 2010;99(6):2739-49. doi: 10.1002/jps.22033.
10. Miller JM, Beig A, Carr RA, Webster GK, Dahan A. The solubility- permeability interplay when using cosolvents for solubilization: Revising the way we use solubility-enabling formulations. Mol Pharm. 2012;9(3):581-90. doi: 10.1021/mp200460u.
11. Miller JM, Beig A, Krieg BJ, Carr RA, Borchardt TB, Amidon GE, et al. The solubility-permeability interplay: mechanistic modeling and predictive application of the impact of micellar solubilization on intestinal permeation. Mol Pharm. 2011;8(5):1848-56. doi: 10.1021/mp200181v.
12. Miller JM, Dahan A. Predicting the solubility-permeability interplay when using cyclodextrins in solubility-enabling formulations: model validation. Int J Pharm. 2012;430(1-2):388-91. doi: 10.1016/j.ijpharm.2012.03.017.
13. Alonzo D, Zhang G, Zhou D, Gao Y, Taylor L. Understanding the behavior of amorphous pharmaceutical systems during dissolution. Pharm Res. 2010;27(4):608-18. doi: 10.1007/s11095-009-0021-1.
14. Alonzo DE, Gao Y, Zhou D, Mo H, Zhang GGZ, Taylor LS. Dissolution and precipitation behavior of amorphous solid dispersions. J Pharm Sci. 2011;100(8):3316-31. doi: 10.1002/jps.22579.
15. Frank KJ, Rosenblatt KM, Westedt U, Hölig P, Rosenberg J, Mägerlein M, et al. Amorphous solid dispersion enhances permeation of poorly soluble ABT-102: True supersaturation vs. apparent solubility enhancement. Int J Pharm. 2012;437(1-2):288-93. doi: 10.1016/j.ijpharm.2012.08. 014.
16. Gardner CR, Walsh CT, Almarsson O. Drugs as materials: Valuing physical form in drug discovery. Nat Rev Drug Discov. 2004;3(11):926-34.
17. Miller JM, Beig A, Carr RA, Spence JK, Dahan A. A win-win solution in oral delivery of lipophilic drugs: Supersaturation via amorphous solid dispersions increases apparent solubility without sacrifice of intestinal membrane permeability. Mol Pharm. 2012;9(7):2009-16. doi: 10.1021/mp300104s.
18. Newman A, Knipp G, Zografi G. Assessing the performance of amorphous solid dispersions. J Pharm Sci. 2012;101(4):1355-77. doi: 10.1002/jps.23031.
19. Wohnsland F, Faller B. High-throughput permeability pH profile and high-throughput alkane/water log P with artificial membranes. J Med Chem. 2001;44(6):923-30.
20. Miller JM, Dahan A, Gupta D, Varghese S, Amidon GL. Quasi-equilibrium analysis of the ion-pair mediated membrane transport of low-permeability drugs. J Control Release. 2009;137(1):31-7. doi: 10.1016/j.jconrel.2009.02.018.
21. Dahan A, Amidon G. Grapefruit juice and its constituents augment colchicine intestinal absorption: potential hazardous interaction and the role of P-glycoprotein. Pharm Res. 2009;26(4):883-92. doi: 10.1007/s11095-008-9789-7.
22. Dahan A, Amidon GL. Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting. Am J Physiol Gastrointest Liver Physiol. 2009;297(2):G371-7. doi: 10.1152/ajpgi.00102.2009.
23. Dahan A, Sabit H, Amidon GL. Multiple efflux pumps are involved in the transepithelial transport of colchicine: Combined effect of P-gp and MRP2 leads to decreased intestinal absorption throughout the entire small intestine. Drug Metab Dispos. 2009;37(10):2028-36. doi: 10.1124/dmd.109.028282.
24. Dahan A, Amidon GL. Segmental dependent transport of low permeability compounds along the small intestine due to P-glycoprotein: The role of efflux transport in the oral absorption of BCS class III drugs. Mol Pharm. 2009;6(1):19-28. doi: doi:10.1021/mp800088f.
25. Dahan A, Sabit H, Amidon G. The H2 receptor antagonist nizatidine is a P-glycoprotein substrate: Characterization of its intestinal epithelial cell efflux transport. AAPS J. 2009;11(2):205-13. doi: 10.1208/s12248-009-9092-5.
26. Dahan A, West BT, Amidon GL. Segmental-dependent membrane permeability along the intestine following oral drug administration: Evaluation of a triple single-pass intestinal perfusion (TSPIP) approach in the rat. Eur J Pharm Sci. 2009;36(2-3):320-9. doi: 10.1016/j.ejps.2008.10.013.
27. Amidon GL, Lennernas H, Shah VP, Crison JR. A theoretical basis for a biopharmaceutic drug classification: The correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm Res. 1995;12(3):413.
28. Dahan A, Lennernäs H, Amidon GL. The fraction dose absorbed, in humans, and high jejunal human permeability relationship. Mol Pharm. 2012;9(6):1847-51. doi: 10.1021/mp300140h.
29. Dahan A, Miller JM, Hilfinger JM, Yamashita S, Yu LX, Lennernäs H, et al. High-permeability criterion for BCS classification: Segmental/pH dependent permeability considerations. Mol Pharm. 2010;7(5):1827-34. doi: 10.1021/mp100175a.
30. Lennernäs H. Intestinal permeability and its relevance for absorption and elimination. Xenobiotica. 2007;37(10-11):1015-51.