A review of drug solubility in human intestinal fluids: Implications for the prediction of oral absorption

European Journal of Pharmaceutical Sciences

Volumn 57, Issue 1, 2014, Pages 322-332

  Augustijns, Patrick ^a   Wuyts, Benjamin ^a   Hens, Bart ^a   Annaert, Pieter ^a   Butler, James ^b   Brouwers, Joachim ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Duodenal solubility; Human intestinal fluid; Jejunal solubility; Oral absorption; Simulated intestinal fluid; Solubility

Indexed keywords

ACCURACY; AGE DISTRIBUTION; CORRELATION ANALYSIS; DRUG ABSORPTION; DRUG DEVELOPMENT; DRUG SOLUBILITY; DUODENUM; FOOD; HIGH THROUGHPUT SCREENING; HUMAN; INTESTINE ABSORPTION; INTESTINE FLUID; IONIZATION; JEJUNUM; LIPID DEGRADATION; MICELLE; ORAL DRUG ADMINISTRATION; PREDICTIVE VALUE; PRIORITY JOURNAL; REVIEW; SIMULATION; STOMACH PH; BIOLOGICAL MODEL; CHEMISTRY; DIET RESTRICTION; DRUG DOSAGE FORM; FOOD DRUG INTERACTION; INTESTINAL SECRETIONS; METABOLISM; PERMEABILITY; PHARMACEUTICS; PHARMACOKINETICS; POSTPRANDIAL STATE; PROCEDURES; SMALL INTESTINE; SOLUBILITY;

DRUG; DRUG DOSAGE FORM;

ADMINISTRATION, ORAL; BIOPHARMACEUTICS; DOSAGE FORMS; FASTING; FOOD-DRUG INTERACTIONS; HUMANS; INTESTINAL ABSORPTION; INTESTINAL SECRETIONS; INTESTINE, SMALL; MODELS, BIOLOGICAL; PERMEABILITY; PHARMACEUTICAL PREPARATIONS; PHARMACOKINETICS; POSTPRANDIAL PERIOD; SOLUBILITY;

EID: 84899631569     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2013.08.027     Document Type: Review

References (41)

1. J. Alsenz, and M. Kansy High throughput solubility measurement in drug discovery and development Adv. Drug Deliv. Rev. 59 2007 546 567 (Pubitemid 47285404)
2. P. Annaert, J. Brouwers, A. Bijnens, F. Lammert, J. Tack, and P. Augustijns Ex vivo permeability experiments in excised rat intestinal tissue and in vitro solubility measurements in aspirated human intestinal fluids support age-dependent oral drug absorption Eur. J. Pharm. Sci. 39 2010 15 22
3. V. Bakatselou, R.C. Oppenheim, and J.B. Dressman Solubilization and wetting effects of bile salts on the dissolution of steroids Pharm. Res. 8 1991 1461 1469
4. L.Z. Benet, F. Broccatelli, and T.I. Oprea BDDCS applied to over 900 drugs AAPS J. 13 2011 519 547
5. E. Bergman, P. Forsell, E.M. Persson, L. Knutson, P. Dickinson, R. Smith, H. Swaisland, M.R. Farmer, M.V. Cantarini, and H. Lennernäs Pharmacokinetics of gefitinib in humans: the influence of gastrointestinal factors Int. J. Pharm. 341 2007 134 142 (Pubitemid 47096678)
6. J. Bevernage, J. Brouwers, S. Clarysse, M. Vertzoni, J. Tack, P. Annaert, and P. Augustijns Drug supersaturation in simulated and human intestinal fluids representing different nutritional states J. Pharm. Sci. 99 2010 4525 4534
7. J. Bevernage, T. Forier, J. Brouwers, J. Tack, P. Annaert, and P. Augustijns Excipient-mediated supersaturation stabilization in human intestinal fluids Mol. Pharm. 8 2011 564 570
8. J.E. Boni, R.S. Brickl, and J. Dressman Is bicarbonate buffer suitable as a dissolution medium? J. Pharm. Pharmacol. 59 2007 1375 1382 (Pubitemid 47606452)
9. L. Bønløkke, L. Hovgaard, H.G. Kristensen, L. Knutson, and H. Lennernäs Direct estimation of the in vivo dissolution of spironolactone, in two particle size ranges, using the single-pass perfusion technique (Loc-I-Gut) in humans Eur. J. Pharm. Sci. 12 2001 239 250
10. J. Brouwers, J. Tack, and P. Augustijns In vitro behavior of a phosphate ester prodrug of amprenavir in human intestinal fluids and in the Caco-2 system: illustration of intraluminal supersaturation Int. J. Pharm. 336 2007 302 309 (Pubitemid 46670658)
11. S. Carlert, A. Pålsson, G. Hanisch, C. von Corswant, C. Nilsson, L. Lindfors, H. Lennernäs, and B. Abrahamsson Predicting intestinal precipitation: a case example for a basic BCS class II drug Pharm. Res. 27 2010 2119 2130
12. S. Clarysse, D. Psachoulias, J. Brouwers, J. Tack, P. Annaert, G. Duchateau, C. Reppas, and P. Augustijns Postprandial changes in solubilizing capacity of human intestinal fluids for BCS class II drugs Pharm. Res. 26 2009 1456 1466
13. S. Clarysse, J. Brouwers, J. Tack, P. Annaert, and P. Augustijns Intestinal drug solubility estimation based on simulated intestinal fluids: comparison with solubility in human intestinal fluids Eur. J. Pharm. Sci. 43 2011 260 269
14. P.A. Dickinson, R. Abu Rmaileh, L. Ashworth, R.A. Barker, W.M. Burke, C.M. Patterson, N. Stainforth, and M. Yasin An investigation into the utility of a multi-compartmental, dynamic, system of the upper gastrointestinal tract to support formulation development and establish bioequivalence of poorly soluble drugs AAPS J. 14 2012 196 205
15. J.B. Dressman, M. Vertzoni, K. Goumas, and C. Reppas Estimating drug solubility in the gastrointestinal tract Adv. Drug Deliv. Rev. 59 2007 591 602 (Pubitemid 47287780)
16. H.M. Fadda, T. Sousa, A.S. Carlsson, B. Abrahamsson, J.G. Williams, D. Kumar, and A.W. Basit Drug solubility in luminal fluids from different regions of the small and large intestine of humans Mol. Pharm. 7 2010 1527 1532
17. E. Galia, E. Nicolaides, D. Hörter, R. Löbenberg, C. Reppas, and J.B. Dressman Evaluation of various dissolution media for predicting in vivo performance of class I and II drugs Pharm. Res. 15 1998 698 705 (Pubitemid 28275645)
18. P. Gribbon, and A. Sewing High-throughput drug discovery: what can we expect from HTS? Drug Discov. Today 10 2005 17 22 (Pubitemid 40164815)
19. T. Heikkilä, M. Karjalainen, K. Ojala, K. Partola, F. Lammert, P. Augustijns, A. Urtti, M. Yliperttula, L. Peltonen, and J. Hirvonen Equilibrium drug solubility measurements in 96-well plates reveal similar drug solubilities in phosphate buffer pH 6.8 and human intestinal fluid Int. J. Pharm. 405 2011 132 136
20. N. Holmstock, R. Mols, P. Annaert, and P. Augustijns In situ intestinal perfusion in knockout mice demonstrates inhibition of intestinal p-glycoprotein by ritonavir causing increased darunavir absorption Drug Metab. Dispos. 38 2010 1407 1410
21. N. Holmstock, T. De Bruyn, J. Bevernage, P. Annaert, R. Mols, J. Tack, and P. Augustijns Exploring food effects on indinavir absorption with human intestinal fluids in the mouse intestine Eur. J. Pharm. Sci. 49 2013 27 32
22. E. Jantratid, N. Janssen, C. Reppas, and J.B. Dressman Dissolution media simulating conditions in the proximal human gastrointestinal tract: an update Pharm. Res. 25 2008 1663 1676
23. L. Kalantzi, K. Goumas, V. Kalioras, B. Abrahamsson, J.B. Dressman, and C. Reppas Characterization of the human upper gastrointestinal contents under conditions simulating bioavailability/bioequivalence studies Pharm. Res. 23 2006 165 176 (Pubitemid 43214673)
24. E.H. Kerns High throughput physicochemical profiling for drug discovery J. Pharm. Sci. 90 2001 1838 1858 (Pubitemid 33062605)
25. C.A. Lipinski Drug-like properties and the causes of poor solubility and poor permeability J. Pharmacol. Toxicol. Methods 44 2000 235 249 (Pubitemid 32239479)
26. D.F. McGinnity, J. Collington, R.P. Austin, and R.J. Riley Evaluation of human pharmacokinetics, therapeutic dose and exposure predictions using marketed oral drugs Curr. Drug Metab. 8 2007 463 479 (Pubitemid 47603410)
27. L.J. Naylor, V. Bakatselou, and J.B. Dressman Comparison of the mechanism of dissolution of hydrocortisone in simple and mixed micelle systems Pharm. Res. 10 1993 865 870 (Pubitemid 23167569)
28. B.L. Pedersen, H. Brøndsted, H. Lennernäs, F.N. Christensen, A. Müllertz, and H.G. Kristensen Dissolution of hydrocortisone in human and simulated intestinal fluids Pharm. Res. 17 2000 183 189 (Pubitemid 30158367)
29. B.L. Pedersen, A. Müllertz, H. Brøndsted, and H.G. Kristensen A comparison of the solubility of danazol in human and simulated gastrointestinal fluids Pharm. Res. 17 2000 891 894 (Pubitemid 30666973)
30. M. Perez de la Cruz Moreno, M. Oth, S. Deferme, F. Lammert, J. Tack, J. Dressman, and P. Augustijns Characterization of fasted-state human intestinal fluids collected from duodenum and jejunum J. Pharm. Pharmacol. 58 2006 1079 1089 (Pubitemid 44213641)
31. E.M. Persson, A.-S. Gustafsson, A.S. Carlsson, R.G. Nilsson, L. Knutson, P. Forsell, G. Hanisch, H. Lennernäs, and B. Abrahamsson The effects of food on the dissolution of poorly soluble drugs in human and in model small intestinal fluids Pharm. Res. 22 2005 2141 2151 (Pubitemid 41821594)
32. D. Psachoulias, M. Vertzoni, K. Goumas, V. Kalioras, S. Beato, J. Butler, and C. Reppas Precipitation in and supersaturation of contents of the upper small intestine after administration of two weak bases to fasted adults Pharm. Res. 28 2011 3145 3158
33. D. Psachoulias, M. Vertzoni, J. Butler, D. Busby, M. Symillides, J. Dressman, and C. Reppas 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 2012 3486 3498
34. C. Rupp, H. Steckel, and B.W. Müller Solubilization of poorly water-soluble drugs by mixed micelles based on hydrogenated phosphatidylcholine Int. J. Pharm. 395 2010 272 280
35. E. Söderlind, E. Karlsson, A. Carlsson, R. Kong, A. Lenz, S. Lindborg, and J.J. Sheng Simulating fasted human intestinal fluids: understanding the roles of lecithin and bile acids Mol. Pharm. 7 2010 1498 1507
36. S. Stegemann, F. Leveiller, D. Franchi, H. de Jong, and H. Lindén When poor solubility becomes an issue: from early stage to proof of concept Eur. J. Pharm. Sci. 31 2007 249 261 (Pubitemid 47079001)
37. V.H. Sunesen, B.L. Pedersen, H.G. Kristensen, and A. Müllertz In vivo in vitro correlations for a poorly soluble drug, danazol, using the flow-through dissolution method with biorelevant dissolution media Eur. J. Pharm. Sci. 24 2005 305 313 (Pubitemid 40283513)
38. M. Vertzoni, C. Markopoulos, M. Symillides, C. Goumas, G. Imanidis, and C. Reppas Luminal lipid phases after administration of a triglyceride solution of danazol in the fed state and their contribution to the flux of danazol across caco-2 cell monolayers Mol. Pharm. 9 2012 1189 1198
39. W.P. Walters, J. Green, J.R. Weiss, and M.A. Murcko What do medicinal chemists actually make? A 50-year retrospective J. Med. Chem. 54 2011 6405 6416
40. M.C. Wenlock, R.P. Austin, P. Barton, A.M. Davis, and P.D. Leeson A comparison of physiochemical property profiles of development and marketed oral drugs J. Med. Chem. 46 2003 1250 1256 (Pubitemid 36428230)
41. T.S. Wiedmann, and L. Kamel Examination of the solubilization of drugs by bile salt micelles J. Pharm. Sci. 91 2002 1743 1764 (Pubitemid 34810521)