Ethanol effects on apparent solubility of poorly soluble drugs in simulated intestinal fluid

Molecular Pharmaceutics

Volumn 9, Issue 7, 2012, Pages 1942-1952

  Fagerberg, Jonas H ^a   Al Tikriti, Yassir ^a   Ragnarsson, Gert ^b   Bergström, Christel A S ^a,c  

^a UPPSALA UNIVERSITY   (Sweden)

^b MEDICAL PRODUCTS AGENCY   (Sweden)

^c MONASH UNIVERSITY   (Australia)

Author keywords

apparent solubility; biorelevant dissolution medium; dissolution rate; dose number; ethanol; molecular properties; poorly soluble compounds

Indexed keywords

ALBENDAZOLE; ALCOHOL; ASTEMIZOLE; BUFFER; CARVEDILOL; CINNARIZINE; CORTICOSTERONE; DANAZOL; DIPYRIDAMOLE; DISOPYRAMIDE; FELODIPINE; GLIBENCLAMIDE; GRISEOFULVIN; HALOPERIDOL; INDOMETACIN; INDOPROFEN; KETOCONAZOLE; NAPROXEN; OMEPRAZOLE; PHOSPHATE; PHOSPHATIDYLCHOLINE; PROGESTERONE; TAMOXIFEN; TAUROCHOLIC ACID; TERFENADINE; TOLFENAMIC ACID; WARFARIN;

ACIDITY; AREA UNDER THE CURVE; ARTICLE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CORRELATION COEFFICIENT; CRYSTAL STRUCTURE; CYCLOADDITION; DISSOLUTION; DRUG ABSORPTION; DRUG PURITY; DRUG SOLUBILITY; INTESTINE FLUID; LIPOPHILICITY; MAXIMUM PLASMA CONCENTRATION; MOLECULAR WEIGHT; MOLECULE; PH; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; SIMULATION; SOLID STATE;

BODY FLUIDS; ETHANOL; HYDROGEN-ION CONCENTRATION; INTESTINAL ABSORPTION; INTESTINES; PHARMACEUTICAL PREPARATIONS; SOLUBILITY; TRANSITION TEMPERATURE;

EID: 84863318320     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp2006467     Document Type: Article

References (40)

1. 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 Rev. 1997, 23 (1-3) 3-25
2. Benet, L. Z.; Wu, C. Y.; Custodio, J. M. Predicting drug absorption and the effects of food on oral bioavailability Bull. Tech. Gattefosse 2006, 99) 9-16
3. FDA. Guidance for Industry. Waiver of in vivo bioavailability and bioequivalence studies for immediate-release solid oral dosage forms based on a biopharmaceutics classification system. For further information: http://www.fda.gov/downloads/Drugs/GuidanceComplianceRegulatoryInformation/ Guidances/UCM070246.pdf (accessed June 10, 2011), 2000.
4. Yazdanian, M.; Briggs, K.; Jankovsky, C.; Hawi, A. The "High Solubility" Definition of the Current FDA Guidance on Biopharmaceutical Classification System May Be Too Strict for Acidic Drugs Pharm. Res. 2004, 21 (2) 293-299
5. Yu, L. X.; Amidon, G. L.; Polli, J. E.; Zhao, H.; Mehta, M. U.; Conner, D. P.; Shah, V. P.; Lesko, L. J.; Chen, M. L.; Lee, V. H. L.; Hussain, A. S. Biopharmaceutics classification system: The scientific basis for biowaiver extensions Pharm. Res. 2002, 19 (7) 921-925
6. Fagerberg, J. H.; Tsinman, O.; Sun, N.; Tsinman, K.; Avdeef, A.; Bergström, C. A. S. Dissolution rate and apparent solubility of poorly soluble drugs in biorelevant dissolution media Mol. Pharmaceutics 2010, 7 (5) 1419-1430
7. Dressman, J. B.; Reppas, C. In vitro-in vivo correlations for lipophilic, poorly water-soluble drugs Eur. J. Pharm. Sci. 2000, 11 (Suppl. 2) S73-S80
8. 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 (8) 1079-1089
9. Persson, E. M.; Gustafsson, A. S.; Carlsson, A. S.; Nilsson, R. G.; Knutson, L.; Forsell, P.; Hanisch, G.; Lennernäs, 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 (12) 2141-2151
10. Sunesen, V. H.; Pedersen, B. L.; Kristensen, H. G.; Müllertz, A. 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. 2005, 24 (4) 305-313
11. Lehto, P.; Kortejärvi, H.; Liimatainen, A.; Ojala, K.; Kangas, H.; Hirvonen, J.; Tanninen, V. P.; Peltonen, L. Use of conventional surfactant media as surrogates for FaSSIF in simulating in vivo dissolution of BCS class II drugs Eur. J. Pharm. Biopharm. 2011, 78 (3) 531-538
12. Taupitz, T.; Klein, S. Can biorelevant media be simplified by using SLS and Tween 80 to replace bile compounds? Open Drug Delivery J. 2010, 4 (SPEC. ISSUE 1) 30-37
13. Zoeller, T.; Klein, S. Simplified biorelevant media for screening dissolution performance of poorly soluble drugs Dissolution Technol. 2007, 14 (4) 8-13
14. 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 (7) 1663-1676
15. Ilardia-Arana, D.; Kristensen, H. G.; Müllertz, A. Biorelevant dissolution media: Aggregation of amphiphiles and solubility of estradiol J. Pharm. Sci. 2006, 95 (2) 248-255
16. Galia, E.; Nicolaides, E.; Hörter, D.; Löbenberg, 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
17. Boni, J. E.; Brickl, R. S.; Dressman, J.; Pfefferle, M. L. Instant FaSSIF and FeSSIF-Biorelevance meets practicality Dissolution Technol. 2009, 16 (3) 41-45
18. Ottaviani, G.; Gosling, D. J.; Patissier, C.; Rodde, S.; Zhou, L.; Faller, B. What is modulating solubility in simulated intestinal fluids? Eur. J. Pharm. Sci. 2010, 41 (3-4) 452-457
19. Söderlind, E.; Karlsson, E.; Carlsson, A.; Kong, R.; Lenz, A.; Lindborg, S.; Sheng, J. J. Simulating fasted human intestinal fluids: Understanding the roles of lecithin and bile acids Mol. Pharmaceutics 2010, 7 (5) 1498-1507
20. Zaki, N. M.; Artursson, P.; Bergström, C. A. S. A modified physiological BCS for prediction of intestinal absorption in drug discovery Mol. Pharmaceutics 2010, 7 (5) 1478-1487
21. Kawai, Y.; Fujii, Y.; Tabata, F.; Ito, J.; Yukiko, M.; Kameda, A.; Akimoto, K.; Takahashi, M. Profiling and trend analysis of food effects on oral drug absorption considering micelle interaction and solubilization by bile micelles Drug Metab. Pharmacokinet. 2011, 26 (2) 180-191
22. Lennernäs, H. Ethanol-drug absorption interaction: Potential for a significant effect on the plasma pharmacokinetics of ethanol vulnerable formulations Mol. Pharmaceutics 2009, 6 (5) 1429-1440
23. Hendeles, L.; Iafrate, R. P.; Weinberger, M. A clinical and pharamacokinetic basis for the selection and use of slow release theophylline products Clin. Pharmacokinet. 1984, 9 (2) 95-135
24. Yeh, K. C. Indomethacin and indomethacin sustained release - A comparison of their pharmacokinetic profiles Semin. Arthritis Rheum. 1982, 12 (2, Suppl. 1) 136-141
25. Walden, M.; Nicholls, F. A.; Smith, K. J.; Tucker, G. T. The effect of ethanol on the release of opioids from oral prolonged-release preparations Drug Dev. Ind. Pharm. 2007, 33 (10) 1101-1111
26. Fadda, H. M.; Mohamed, M. A. M.; Basit, A. W. Impairment of the in vitro drug release behaviour of oral modified release preparations in the presence of alcohol Int. J. Pharm. 2008, 360 (1-2) 171-176
27. Levina, M.; Vuong, H.; Rajabi-Siahboomi, A. R. The influence of hydro-alcoholic media on hypromellose matrix systems Drug Dev. Ind. Pharm. 2007, 33 (10) 1125-1134
28. Traynor, M. J.; Brown, M. B.; Pannala, A.; Beck, P.; Martin, G. P. Influence of alcohol on the release of tramadol from 24-h controlled-release formulations during in vitro dissolution experiments Drug Dev. Ind. Pharm. 2008, 34 (8) 885-889
29. FDA. Suggests Dissolution tests of MR products in acidic media containing 5%, 20% and 40% ethanol in Draft Guidances on Bupropion Hydrochloride, Desvenlafaxine Succinate, Lamotrigine, Morphine Sulfate, Quetiapine Fumarate, Ropinirole Hydrochloride, Trazodone Hydrochloride, Trospium Chloride and Venlafaxine Hydrochloride. For further information: http://www.fda.gov/ downloads/Drugs/GuidanceComplianceRegulatoryInformation/Guidances/... UCM082973.pdf, UCM179177.pdf, UCM209231.pdf, UCM234971.pdf, UCM089520.pdf, UCM194667.pdf, UCM261531.pdf, UCM090751.pdf and UCM091259.pdf (accessed June 10, 2011).
30. Avdeef, A.; Tsinman, O. Miniaturized rotating disk intrinsic dissolution rate measurement: Effects of buffer capacity in comparisons to traditional wood's apparatus Pharm. Res. 2008, 25 (11) 2613-2627
31. Bijlani, V.; Yuonayel, D.; Katpally, S.; Chukwumezie, B. N.; Adeyeye, M. C. Monitoring ibuprofen release from multiparticulates: In situ fiber-optic technique versus the HPLC method: A technical note. AAPS PharmSciTech 2007, 8 (3).
32. Tsinman, K.; Avdeef, A.; Tsinman, O.; Voloboy, D. Powder dissolution method for estimating rotating disk intrinsic dissolution rates of low solubility drugs Pharm. Res. 2009, 26 (9) 2093-2100
33. Amidon, G. L.; Lennernaes, 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
34. Mithani, S. D.; Bakatselou, V.; TenHoor, C. N.; Dressman, J. B. Estimation of the increase in solubility of drugs as a function of bile salt concentration Pharm. Res. 1996, 13 (1) 163-167
35. Åkerlöf, G. Dielectric constants of some organic solvent-water mixtures at various temperatures J. Am. Chem. Soc. 1932, 54 (11) 4125-4139
36. Kawakami, K.; Oda, N.; Miyoshi, K.; Funaki, T.; Ida, Y. Solubilization behavior of a poorly soluble drug under combined use of surfactants and cosolvents Eur. J. Pharm. Sci. 2006, 28 (1-2) 7-14
37. Suzuki, H. Studies of the Effect of Ethanol and Sodium Chloride on the Micellization of Sodium Dodecyl Sulfate by Gel Filtration Bull. Chem. Soc. Jpn. 1976, 49 (6) 1470-1474
38. Zana, R. Aqueous surfactant-alcohol systems: A review Adv. Colloid Interface Sci. 1995, 57 (C) 1-64
39. O'Neil, M. J., Ed. The Merck Index, 13 th ed.; Merck: 2001
40. Bergström, C. A. S.; Wassvik, C. M.; Johansson, K.; Hubatsch, I. Poorly soluble marketed drugs display solvation limited solubility J. Med. Chem. 2007, 50 (23) 5858-5862