In vitro-in vivo correlation of the effect of supersaturation on the intestinal absorption of BCS class 2 drugs

Molecular Pharmaceutics

Volumn 11, Issue 3, 2014, Pages 746-754

  Higashino, Haruki ^a   Hasegawa, Tsubasa ^a   Yamamoto, Mari ^a   Matsui, Rie ^a   Masaoka, Yoshie ^a   Kataoka, Makoto ^a   Sakuma, Shinji ^a   Yamashita, Shinji ^a  

^a SETSUNAN UNIVERSITY   (Japan)

Author keywords

in vitro in vivo correlation; oral drug absorption; poorly water soluble drugs; supersaturation

Indexed keywords

1 AMINOBENZOTRIAZOLE; ALBENDAZOLE; CYTOCHROME P450; DIPYRIDAMOLE; GEFITINIB; KETOCONAZOLE; ANTINEOPLASTIC AGENT; CYTOCHROME P450 3A INHIBITOR; QUINAZOLINE DERIVATIVE; SOLVENT; TUBULIN MODULATOR; VASODILATOR AGENT;

ANIMAL MODEL; ARTICLE; CHEMICAL PROCEDURES; CONCENTRATION RESPONSE; CONTROLLED STUDY; CORRELATION ANALYSIS; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DISSOLUTION; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG DOSAGE FORM; DRUG EFFECT; DRUG METABOLISM; DRUG SOLUBILITY; FASTED STATE SIMULATED INTESTINAL FLUID; IN VITRO STUDY; IN VIVO STUDY; INTESTINE ABSORPTION; INTESTINE FLUID; LIVER METABOLISM; MALE; NONHUMAN; POWDER; PRECIPITATION; PRIORITY JOURNAL; RAT; STOMACH PH; ANIMAL; CHEMISTRY; DRUG EFFECTS; DRUG STABILITY; ORAL DRUG ADMINISTRATION; SOLUBILITY; SPRAGUE DAWLEY RAT;

ADMINISTRATION, ORAL; ALBENDAZOLE; ANIMALS; ANTINEOPLASTIC AGENTS; CALORIMETRY, DIFFERENTIAL SCANNING; CYTOCHROME P-450 CYP3A INHIBITORS; DIPYRIDAMOLE; DRUG STABILITY; IN VITRO TECHNIQUES; INTESTINAL ABSORPTION; KETOCONAZOLE; MALE; QUINAZOLINES; RATS; RATS, SPRAGUE-DAWLEY; SOLUBILITY; SOLVENTS; TUBULIN MODULATORS; VASODILATOR AGENTS;

EID: 84901742364     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp400465p     Document Type: Article

References (55)

1. Lipinski, C. A. Drug-like properties and the causes of poor solubility and poor permeability J. Pharmacol. Toxicol. Methods 2000, 44 (1) 235-249
2. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery 2001, 46 (1-3) 3-26
3. Brouwers, J.; Brewster, M. E.; Augustijns, P. Supersaturating drug delivery systems: the answer to solubility-limited oral bioavailability? J. Pharm. Sci. 2009, 98 (8) 2549-2572
4. Bevernage, J.; Brouwers, J.; Brewster, M. E.; Augustijns, P. Evaluation of gastrointestinal drug supersaturation and precipitation: Strategies and issues Int. J. Pharmaceutics 2013, 453 (1) 25-35
5. Kohri, N.; Yamayoshi, Y.; Xin, H.; Iseki, K.; Sato, N.; Todo, S.; Miyazaki, K. Improving the oral bioavailability of albendazole in rabbits by the solid dispersion technique J. Pharm. Pharmacol. 1999, 51 (2) 159-164
6. Tao, T.; Zhao, Y.; Wu, J.; Zhou, B. Preparation and evaluation of itraconazole dihydrochloride for the solubility and dissolution rate enhancement Int. J. Pharmaceutics 2009, 367 (1-2) 109-114
7. Takano, R.; Takata, N.; Saito, R.; Furumoto, K.; Higo, S.; Hayashi, Y.; Machida, M.; Aso, Y.; Yamashita, S. Quantitative analysis of the effect of supersaturation on in vivo drug absorption Mol. Pharmaceutics 2010, 7 (5) 1431-1440
8. Lu, G. W.; Hawley, M.; Smith, M.; Geiger, B. M.; Pfund, W. Characterization of a novel polymorphic form of celecoxib J. Pharm. Sci. 2006, 95 (2) 305-317
9. Verreck, G.; Six, K.; Van den Mooter, G.; Baert, L.; Peeters, J.; Brewster, M. E. Characterization of solid dispersions of itraconazole and hydroxypropylmethylcellulose prepared by melt extrusion-Part I Int. J. Pharmaceutics 2003, 251 (1-2) 165-174
10. Oshima, T.; Sonoda, R.; Ohkuma, M.; Sunada, H. Preparation of rapidly disintegrating tablets containing itraconazole solid dispersions Chem. Pharm. Bull. 2007, 55 (11) 1557-1562
11. Kennedy, M.; Hu, J.; Gao, P.; Li, L.; Ali-Reynolds, A.; Chal, B.; Gupta, V.; Ma, C.; Mahajan, N.; Akrami, A.; Surapaneni, S. Enhanced bioavailability of a poorly soluble VR1 antagonist using an amorphous solid dispersion approach: a case study Mol. Pharmaceutics 2008, 5 (6) 981-993
12. Shiraki, K.; Takata, N.; Takano, R.; Hayashi, Y.; Terada, K. Dissolution improvement and the mechanism of the improvement from cocrystallization of poorly water-soluble compounds Pharm. Res. 2008, 25 (11) 2581-2592
13. Bak, A.; Gore, A.; Yanez, E.; Stanton, M.; Tufekcic, S.; Syed, R.; Akrami, A.; Rose, M.; Surapaneni, S.; Bostick, T.; King, A.; Neervannan, S.; Ostovic, D.; Koparkar, A. The co-crystal approach to improve the exposure of a water-insoluble compound: AMG 517 sorbic acid co-crystal characterization and pharmacokinetics J. Pharm. Sci. 2008, 97 (9) 3942-3956
14. Castillo, J. A.; Palomo-Canales, J.; Garcia, J. J.; Lastres, J. L.; Bolas, F.; Torrado, J. J. Preparation and characterization of albendazole beta-cyclodextrin complexes Drug Dev. Ind. Pharm. 1999, 25 (12) 1241-1248
15. Phillip Lee, Y. H.; Sathigari, S.; Jean Lin, Y. J.; Ravis, W. R.; Chadha, G.; Parsons, D. L.; Rangari, V. K.; Wright, N.; Babu, R. J. Gefitinib-cyclodextrin inclusion complexes: physico-chemical characterization and dissolution studies Drug Dev. Ind. Pharm. 2009, 35 (9) 1113-1120
16. Gao, P.; Rush, B. D.; Pfund, W. P.; Huang, T.; Bauer, J. M.; Morozowich, W.; Kuo, M. S.; Hageman, M. J. Development of a supersaturable SEDDS (S-SEDDS) formulation of paclitaxel with improved oral bioavailability J. Pharm. Sci. 2003, 92 (12) 2386-2398
17. Carlert, S.; PaÌŠlsson, A.; Hanisch, G.; von Corswant, C.; Nilsson, C.; Lindfors, L.; Lennernäs, H.; Abrahamsson, B. Predicting intestinal precipitation-a case example for a basic BCS class II drug Pharm. Res. 2010, 27 (10) 2119-2130
18. Bevernage, J.; Brouwers, J.; Clarysse, S.; Vertzoni, M.; Tack, J.; Annaert, P.; Augustijns, P. Drug supersaturation in simulated and human intestinal fluids representing different nutritional states J. Pharm. Sci. 2010, 99 (11) 4525-4534
19. Ozaki, S.; Minamisono, T.; Yamashita, T.; Kato, T.; Kushida, I. Supersaturation-nucleation behavior of poorly soluble drugs and its impact on the oral absorption of drugs in thermodynamically high-energy forms J. Pharm. Sci. 2012, 101 (1) 214-222
20. Ozaki, S.; Kushida, I.; Yamashita, T.; Hasebe, T.; Shirai, O.; Kano, K. Evaluation of drug supersaturation by thermodynamic and kinetic approaches for the prediction of oral absorbability in amorphous pharmaceuticals J. Pharm. Sci. 2012, 101 (11) 4220-4230
21. Yeap, Y. Y.; Trevaskis, N. L.; Quach, T.; Tso, P.; Charman, W. N.; Porter, C. J. Intestinal bile secretion promotes drug absorption from lipid colloidal phases via induction of supersaturation Mol. Pharmaceutics 2013, 10 (5) 1874-1889
22. Psachoulias, D.; Vertzoni, M.; Goumas, K.; Kalioras, V.; Beato, S.; Butler, J.; Reppas, C. Precipitation in and supersaturation of contents of the upper small intestine after administration of two weak bases to fasted adults Pharm. Res. 2011, 28 (12) 3145-3158
23. Kostewicz, E. S.; Brauns, U.; Becker, R.; Dressman, J. B. Forecasting the oral absorption behavior of poorly soluble weak bases using solubility and dissolution studies in biorelevant media Pharm. Res. 2002, 19 (3) 345-349
24. Vertzoni, M.; Dressman, J.; Butler, J.; Hempenstall, J.; Reppas, C. Simulation of fasting gastric conditions and its importance for the in vivo dissolution of lipophilic compounds Eur. J. Pharm. Biopharm. 2005, 60 (3) 413-417
25. Sugawara, M.; Kadomura, S.; He, X.; Takekuma, Y.; Kohri, N.; Miyazaki, K. The use of an in vitro dissolution and absorption system to evaluate oral absorption of two weak bases in pH-independent controlled-release formulations Eur. J. Pharm. Sci. 2005, 26 (1) 1-8
26. Vertzoni, M.; Pastelli, E.; Psachoulias, D.; Kalantzi, L.; Reppas, C. Estimation of intragastric solubility of drugs: in what medium? Pharm. Res. 2007, 24 (5) 909-917
27. Wagner, C.; Jantratid, E.; Kesisoglou, F.; Vertzoni, M.; Reppas, C.; Dressman, J. B. Predicting the oral absorption of a poorly soluble, poorly permeable weak base using biorelevant dissolution and transfer model tests coupled with a physiologically based pharmacokinetic model Eur. J. Pharm. Biopharm. 2012, 82 (1) 127-138
28. Sugano, K. Computational oral absorption simulation of free base drugs Int. J. Pharmaceutics 2010, 398 (1-2) 73-82
29. Lelawongs, P.; Barone, J. A.; Colaizzi, J. L.; Hsuan, A. T.; Mechlinski, W.; Legendre, R.; Guarnieri, J. Effect of food and gastric acidity on absorption of orally administered ketoconazole Clin. Pharm. 1988, 7 (3) 228-235
30. Blum, R. A.; D'Andrea, D. T.; Florentino, B. M.; Wilton, J. H.; Hilligoss, D. M.; Gardner, M. J.; Henry, E. B.; Goldstein, H.; Schentag, J. J. Increased gastric pH and the bioavailability of fluconazole and ketoconazole Ann. Intern. Med. 1991, 114 (9) 755-757
31. Kataoka, M.; Itsubata, S.; Masaoka, Y.; Sakuma, S.; Yamashita, S. In vitro dissolution/permeation system to predict the oral absorption of poorly water-soluble drugs: effect of food and dose strength on it Biol. Pharm. Bull. 2011, 34 (3) 401-407
32. Kataoka, M.; Yokoyama, T.; Masaoka, Y.; Sakuma, S.; Yamashita, S. Estimation of P-glycoprotein-mediated efflux in the oral absorption of P-gp substrate drugs from simultaneous analysis of drug dissolution and permeation Eur. J. Pharm. Sci. 2011, 44 (4) 544-551
33. Kataoka, M.; Sugano, K.; da Costa Mathews, C.; Wong, J. W.; Jones, K. L.; Masaoka, Y.; Sakuma, S.; Yamashita, S. Application of dissolution/permeation system for evaluation of formulation effect on oral absorption of poorly water-soluble drugs in drug development Pharm. Res. 2012, 29 (6) 1485-1494
34. Vandecruys, R.; Peeters, J.; Verreck, G.; Brewster, M. E. Use of a screening method to determine excipients which optimize the extent and stability of supersaturated drug solutions and application of this system to solid formulation design Int. J. Pharmaceutics 2007, 342 (1-2) 168-175
35. Yamashita, T.; Ozaki, S.; Kushida, I. Solvent shift method for anti-precipitant screening of poorly soluble drugs using biorelevant medium and dimethyl sulfoxide Int. J. Pharmaceutics 2011, 419 (1-2) 170-174
36. Bevernage, J.; Forier, T.; Brouwers, J.; Tack, J.; Annaert, P.; Augustijns, P. Excipient-mediated supersaturation stabilization in human intestinal fluids Mol. Pharmaceutics 2011, 8 (2) 564-570
37. Bevernage, J.; Hens, B.; Brouwers, J.; Tack, J.; Annaert, P.; Augustijns, P. Supersaturation in human gastric fluids Eur. J. Pharm. Biopharm. 2012, 81 (1) 184-189
38. Balani, S. K.; Zhu, T.; Yang, T. J.; Liu, Z.; He, B.; Lee, F. W. Effective dosing regimen of 1-aminobenzotriazole for inhibition of antipyrine clearance in rats, dogs, and monkeys Drug Metab. Dispos. 2002, 30 (10) 1059-1062
39. Emoto, C.; Murase, S.; Sawada, Y.; Jones, B. C.; Iwasaki, K. In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations catalyzed by human cytochrome P450 enzymes: a comparison with SKF-525A and ketoconazole Drug Metab. Pharmacokinet. 2003, 18 (5) 287-295
40. El-Kattan, A. F.; Poe, J.; Buchholz, L.; Thomas, H. V.; Brodfuehrer, J.; Clark, A. The use of 1-aminobenzotriazole in differentiating the role of CYP-mediated first pass metabolism and absorption in limiting drug oral bioavailability: a case study Drug Metab. Lett. 2008, 2 (2) 120-124
41. Takahashi, M.; Washio, T.; Suzuki, N.; Igeta, K.; Yamashita, S. Investigation of the intestinal permeability and first-pass metabolism of drugs in cynomolgus monkeys using single-pass intestinal perfusion Biol. Pharm. Bull. 2010, 33 (1) 111-116
42. Bylund, J.; Bueters, T. Presystemic metabolism of AZ′0908, a novel mPGES-1 inhibitor: an in vitro and in vivo cross-species comparison J. Pharm. Sci. 2013, 102 (3) 1106-1115
43. Takano, R.; Sugano, K.; Higashida, A.; Hayashi, Y.; Machida, M.; Aso, Y.; Yamashita, S. Oral absorption of poorly water-soluble drugs: computer simulation of fraction absorbed in humans from a miniscale dissolution test Pharm. Res. 2006, 23 (6) 1144-1156
44. Takano, R.; Kataoka, M.; Yamashita, S. Integrating drug permeability with dissolution profile to develop IVIVC Biopharm. Drug Dispos. 2012, 33 (7) 354-365
45. Daniel-Mwambete, K.; Torrado, S.; Cuesta-Bandera, C.; Ponce-Gordo, F.; Torrado, J. J. The effect of solubilization on the oral bioavailability of three benzimidazole carbamate drugs Int. J. Pharmaceutics 2004, 272 (1-2) 29-36
46. Gibbs, M. A.; Thummel, K. E.; Shen, D. D.; Kunze, K. L. Inhibition of cytochrome P-450 3A (CYP3A) in human intestinal and liver microsomes: comparison of Ki values and impact of CYP3A5 expression Drug Metab. Dispos. 1999, 27 (2) 180-187
47. Amidon, G. L.; Lennernas, H.; Shah, V. P.; Crison, J. R. 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) 413-420
48. Sugano, K. A simulation of oral absorption using classical nucleation theory Int. J. Pharmaceutics 2009, 378 (1-2) 142-145
49. Lindfors, L.; Forssén, S.; Westergren, J.; Olsson, U. Nucleation and crystal growth in supersaturated solutions of a model drug J. Colloid Interface Sci. 2008, 325 (2) 404-413
50. Patterson, J. E.; James, M. B.; Forster, A. H.; Lancaster, R. W.; Butler, J. M.; Rades, T. The influence of thermal and mechanical preparative techniques on the amorphous state of four poorly soluble compounds J. Pharm. Sci. 2005, 94 (9) 1998-2012
51. Elsby, R.; Gillen, M.; Butters, C.; Imisson, G.; Sharma, P.; Smith, V.; Surry, D. D. The utility of in vitro data in making accurate predictions of human P-glycoprotein-mediated drug-drug interactions: a case study for AZD5672 Drug Metab. Dispos. 2011, 39 (2) 275-282
52. Khaliq, Y.; Gallicano, K.; Venance, S.; Kravcik, S.; Cameron, D. W. Effect of ketoconazole on ritonavir and saquinavir concentrations in plasma and cerebrospinal fluid from patients infected with human immunodeficiency virus Clin. Pharmacol. Ther. 2000, 68 (6) 637-646
53. Lu, C.; Hatsis, P.; Berg, C.; Lee, F. W.; Balani, S. K. Prediction of pharmacokinetic drug-drug interactions using human hepatocyte suspension in plasma and cytochrome P450 phenotypic data. II. In vitro-in vivo correlation with ketoconazole Drug Metab. Dispos. 2008, 36 (7) 1255-1260
54. Abbas, R.; Hug, B. A.; Leister, C.; Burns, J.; Sonnichsen, D. Pharmacokinetics of oral neratinib during co-administration of ketoconazole in healthy subjects Br. J. Clin. Pharmacol. 2011, 71 (4) 522-527
55. An, G.; Liu, W.; Katz, D. A.; Marek, G.; Awni, W.; Dutta, S. Effect of ketoconazole on the pharmacokinetics of the 11β-hydroxysteroid dehydrogenase type 1 inhibitor ABT-384 and its two active metabolites in healthy volunteers: population analysis of data from a drug-drug interaction study Drug Metab. Dispos. 2013, 41 (5) 1035-1045