Simulating fasted human intestinal fluids: Understanding the roles of lecithin and bile acids

Molecular Pharmaceutics

Volumn 7, Issue 5, 2010, Pages 1498-1507

  Söderlind, Erik ^a   Karlsson, Eva ^a   Carlsson, Anders ^a   Kong, Rui ^a   Lenz, Anna ^a   Lindborg, Sara ^a   Sheng, Jennifer J ^b  

^a ASTRAZENECA R AND D   (Sweden)

^b ASTRAZENECA   (United Kingdom)

Author keywords

bile acids; drug solubility; Intestinal fluids; lecithin

Indexed keywords

AMINO ACID; AMIODARONE; ATOVAQUONE; BILE ACID; BILE SALT; CARBAMAZEPINE; CARVEDILOL; CYCLOSPORIN; CYCLOSPORIN A; DANAZOL; DICLOFENAC; DIETHYLSTILBESTROL; DIPYRIDAMOLE; FELODIPINE; FLUFENAMIC ACID; GLYCINE; GLYCOCHENODEOXYCHOLIC ACID; GLYCOCHOLIC ACID; GLYCODEOXYCHOLIC ACID; GRISEOFULVIN; IRBESARTAN; PHOSPHATE; PHOSPHATIDYLCHOLINE; PROBUCOL; RETINOL; STEROID; TAURINE; TAUROCHOLIC ACID; TAURODEOXYCHOLIC ACID; UNINDEXED DRUG;

AQUEOUS SOLUTION; ARTICLE; BILE; CONJUGATION; CONTROLLED STUDY; DRUG FORMULATION; DRUG SOLUBILITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROXYLATION; IN VIVO STUDY; INTESTINE FLUID; LIGHT SCATTERING; PH; PREDICTION; PRIORITY JOURNAL; PRODUCT DEVELOPMENT; SOLUBILIZATION;

BILE ACIDS AND SALTS; BODY FLUIDS; CHEMISTRY, PHARMACEUTICAL; DRUG DISCOVERY; FASTING; HUMANS; HYDROGEN-ION CONCENTRATION; INTESTINAL ABSORPTION; INTESTINE, SMALL; LECITHINS; MODELS, BIOLOGICAL; PHARMACOKINETICS; SOLUBILITY; THERAPEUTIC EQUIVALENCY;

EID: 77957738361     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp100144v     Document Type: Article

References (32)

1. Lindahl, A.; Ungell, A. L.; Knutson, L.; Lennernas, H. Characterization of fluids from the stomach and proximal jejunum in men and women Pharm. Res. 1997, 14, 497-502
2. Dressman, J. B.; Amidon, G. L.; Reppas, C.; Shah, V. P. Dissolution testing as a prognostic tool for oral drug absorption: immediate release dosage forms Pharm. Res. 1998, 15, 11-22
3. Pedersen, B. L.; Brondsted, H.; Lennernas, H.; Christensen, F. N.; Mullertz, A.; Kristensen, H. G. Dissolution of hydrocortisone in human and simulated intestinal fluids Pharm. Res. 2000, 17, 183-189
4. 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, 345-349
5. Vertzoni, M.; Fotaki, N.; Kostewicz, E.; Stippler, E.; Leuner, C.; Nicolaides, E.; Dressman, J.; Reppas, C. Dissolution media simulating the intralumenal composition of the small intestine: physiological issues and practical aspects J. Pharm. Pharmacol. 2004, 56, 453-462
6. Persson, E. M.; Gustafsson, A. S.; Carlsson, A. S.; Nilsson, R. G.; Knutson, L.; Forsell, P.; Hanisch, G.; Lennernas, H.; Abrahamsson, B. The effects of food on the dissolution of poorly soluble drugs in human and in model small intestinal fluids Pharm. Res. 2005, 22, 2141-2151
7. Perez de la Cruz Moreno, M.; Oth, M.; Deferme, S.; Lammert, F.; Tack, J.; Dressman, J.; Augustijns, P. Characterization of fasted-state human intestinal fluids collected from duodenum and jejunum J. Pharm. Pharmacol. 2006, 58, 1079-1089
8. Gray, V. A.; Dressman, J. B. Change of pH requirements for simulated intestinal fluid TS Pharmacopeial Forum 1996, 22, 1943-1945
9. Galia, E.; Nicolaides, E.; Horter, D.; Lobenberg, R.; Reppas, C.; Dressman, J. B. Evaluation of various dissolution media for predicting in vivo performance of class I and II drugs Pharm. Res. 1998, 15, 698-705
10. Kalantzi, L.; Goumas, K.; Kalioras, V.; Abrahamsson, B.; Dressman, J. B.; Reppas, C. Characterization of the human upper gastrointestinal contents under conditions simulating bioavailability/bioequivalence studies Pharm. Res. 2006, 23, 165-176
11. Kalantzi, L.; Persson, E.; Polentarutti, B.; Abrahamsson, B.; Goumas, K.; Dressman, J. B.; Reppas, C. Canine intestinal contents vs. simulated media for the assessment of solubility of two weak bases in the human small intestinal contents Pharm. Res. 2006, 23, 1373-1381
12. Jantratid, E.; Janssen, N.; Reppas, C.; Dressman, J. B. Dissolution media simulating conditions in the proximal human gastrointestinal tract: an update Pharm. Res. 2008, 25, 1663-1676
13. Lennernas, H.; Ahrenstedt, O.; Hallgren, R.; Knutson, L.; Ryde, M.; Paalzow, L. K. Regional jejunal perfusion, a new in vivo approach to study oral drug absorption in man Pharm. Res. 1992, 9, 1243-1251
14. Knutson, L.; Odlind, B.; Hallgren, R. A new technique for segmental jejunal perfusion in man Am. J. Gastroenterol. 1989, 84, 1278-1284
15. Söderlind, E.; Dressman, J. B. Physiological factors affecting drug release and absorption in the gastrointestinal tract. In Oral Drug Absorption: Prediction and Assessment, 2nd ed.; Dressman, J. B.; Reppas, C., Eds.; Informa Healthcare: New York, 2010; pp 1 - 20.
16. Small, D. In The physical chemistry of lipids: from alkanes to phospholipids; Plenum Press: New York, 1986.
17. Mazer, N. A.; Benedek, G. B.; Carey, M. C. Quasielastic light-scattering studies of aqueous biliary lipid systems. Mixed micelle formation in bile salt-lecithin solutions Biochemistry 1980, 19, 601-615
18. Dressman, J. B.; Vertzoni, M.; Goumas, K.; Reppas, C. Estimating drug solubility in the gastrointestinal tract Adv. Drug Delivery Rev. 2007, 59, 591-602
19. Balakrishnan, A.; Rege, B. D.; Amidon, G. L.; Polli, J. E. Surfactant-mediated dissolution: contributions of solubility enhancement and relatively low micelle diffusivity J. Pharm. Sci. 2004, 93, 2064-2075
20. Granero, G. E.; Ramachandran, C.; Amidon, G. L. Dissolution and solubility behavior of fenofibrate in sodium lauryl sulfate solutions Drug Dev. Ind. Pharm. 2005, 31, 917-922
21. Sheng, J. J.; Kasim, N. A.; Chandrasekharan, R.; Amidon, G. L. Solubilization and dissolution of insoluble weak acid, ketoprofen: effects of pH combined with surfactant Eur. J. Pharm. Sci. 2006, 29, 306-314
22. Clarysse, S.; Psachoulias, D.; Brouwers, J.; Tack, J.; Annaert, P.; Duchateau, G.; Reppas, C.; Augustijns, P. Postprandial changes in solubilizing capacity of human intestinal fluids for BCS class II drugs Pharm. Res. 2009, 26, 1456-1466
23. Clarysse, S.; Tack, J.; Lammert, F.; Duchateau, G.; Reppas, C.; Augustijns, P. Postprandial evolution in composition and characteristics of human duodenal fluids in different nutritional states J. Pharm. Sci. 2009, 98, 1177-1192
24. Nicolaides, E.; Galia, E.; Efthymiopoulos, C.; Dressman, J. B.; Reppas, C. Forecasting the in vivo performance of four low solubility drugs from their in vitro dissolution data Pharm. Res. 1999, 16, 1876-1882
25. Llinàs, A.; Glen, R. C.; Goodman, J. M. Solubility challenge: Can you predict solubilities of 32 molecules using a database of 100 reliable measurements? J. Chem. Inf. Model. 2008, 48, 1289-1303
26. Tosco, P.; Rolando, B.; Fruttero, R.; Henchoz, Y.; Martel, S.; Carrupt, P.-A.; Gasco, A. Physicochemical profiling of sartans: A detailed study of ionization constants and distribution coefficients Helv. Chim. Acta 2008, 91, 468-482
27. Dellis, D.; Giaginis, C.; Tsantili-Kakoulidou, A. Physicochemical profile of nimesulide. Exploring the interplay of lipophilicity, solubility and ionization J. Pharm. Biomed. Anal. 2007, 44, 57-62
28. Zhou, C.; Jin, Y.; Kenseth, J. R.; Stella, M.; Wehmeyer, K. R.; Heineman, W. R. Rapid pKa estimation using vacuum-assisted multiplexed capillary electrophoresis (VAMCE) with ultraviolet detection J. Pharm. Sci. 2005, 94, 576-589
29. Bergstrom, C. A. S.; Luthman, K.; Artursson, P. Accuracy of calculated pH-dependent aqueous drug solubility Eur. J. Pharm. Sci. 2004, 22, 387-398
30. Kochansky, C. J.; McMasters, D. R.; Lu, P.; Koeplinger, K. A.; Kerr, H. H.; Shou, M.; Korzekwa, K. R. Impact of pH on plasma protein binding in equilibrium dialysis Mol. Pharmaceutics 2008, 5, 438-448
31. Vertzoni, M.; Pastelli, E.; Psachoulias, D.; Kalantzi, L.; Reppas, C. Estimation of intragastric solubility of drugs: In what medium Pharm. Res. 2007, 24, 909-917
32. Sköld, C.; Winiwarter, S.; Wernevik, J.; Bergström, F.; Engström, L.; Allen, R.; Box, K.; Comer, J.; Mole, J.; Hallberg, A.; Lennernäs, H.; Lundstedt, T.; Ungell, A.-L.; Karlén, A. Presentation of structurally diverse and commercially available drug data set for correlation and benchmarking studies J. Med. Chem. 2006, 49, 6660-6671