Provisional in-silico biopharmaceutics classification (BCS) to guide oral drug product development

Drug Design, Development and Therapy

Volumn 8, Issue , 2014, Pages 1563-1575

  Wolk, Omri ^a   Agbaria, Riad ^a   Dahan, Arik ^a  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

Author keywords

Biopharmaceutics classification system; In silico; Intestinal permeability; Partition coefficient; Solubility

Indexed keywords

ARTICLE; BIOPHARMACEUTICS CLASSIFICATION SYSTEM; COMPUTER ANALYSIS; COMPUTER MODEL; COMPUTER PREDICTION; CONTROLLED STUDY; DATA ANALYSIS SOFTWARE; DRUG CLASSIFICATION; DRUG PENETRATION; DRUG SOLUBILITY; DRUG STRUCTURE; HUMAN; HUMAN TISSUE; MELTING POINT; ORAL DRUG ADMINISTRATION; PHYSICAL CHEMISTRY; PRODUCT DEVELOPMENT; REFERENCE VALUE; THERMODYNAMICS; ALGORITHM; COMPUTER PROGRAM; COMPUTER SIMULATION; DRUG DEVELOPMENT; PERMEABILITY; PHARMACEUTICS; SOLUBILITY;

DRUG;

ADMINISTRATION, ORAL; ALGORITHMS; BIOPHARMACEUTICS; COMPUTER SIMULATION; DRUG DISCOVERY; HUMANS; PERMEABILITY; PHARMACEUTICAL PREPARATIONS; SOFTWARE; SOLUBILITY; THERMODYNAMICS;

EID: 84908073820     PISSN: None     EISSN: 11778881     Source Type: Journal    
DOI: 10.2147/DDDT.S68909     Document Type: Article

References (80)

1. Dahan A, Lennernäs H, Amidon GL. The fraction dose absorbed, in humans, and high jejunal human permeability relationship. Mol Pharm. 2012;9(6):1847-1851.
2. Lennernäs H, Abrahamsson B. The use of biopharmaceutic classification of drugs in drug discovery and development: current status and future extension. J Pharm Pharmacol. 2005;57(3):273-285.
3. Amidon GL, Lennernäs 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): 413-420.
4. Amidon KS, Langguth P, Lennernäs H, Yu LX, Amidon GL. Bioequivalence of oral products and the biopharmaceutics classification system: science, regulation, and public policy. Clin Pharmacol Ther. 2011; 90(3):467-470.
5. Dahan A, Miller JM, Amidon GL. Prediction of solubility and permeability class membership: provisional BCS classification of the world's top oral drugs. AAPS J. 2009;11(4):740-746.
6. Löbenberg R, Amidon GL. Modern bioavailability, bioequivalence and biopharmaceutics classification system. New scientific approaches to international regulatory standards. Eur J Pharm Biopharm. 2000; 50(1):3-12.
7. Martinez MN, Amidon GL. A mechanistic approach to understanding the factors affecting drug absorption: a review of fundamentals. J Clin Pharmacol. 2002;42(6):620-643.
8. Center for Drug Evaluation and Research, US Food and Drug Administration. Guidance for Industry: Waiver of In Vivo Bioavailability and Bioequivalence Studies for Immediate-release Solid Oral Dosage Forms Based on a Biopharmaceutics Classification System. Rockville (MD): FDA; 2000.
9. Yu LX, Amidon G, Polli J, et al. Biopharmaceutics classification system: the scientific basis for biowaiver extensions. Pharm Res. 2002; 19(7):921-925.
10. Cook J, Addicks W, Wu Y. Application of the biopharmaceutical classification system in clinical drug development-an industrial view. AAPS J. 2008;10(2):306-310.
11. Ku MS. Use of the biopharmaceutical classification system in early drug development. AAPS J. 2008;10(1):208-212.
12. Pham-The H, Garrigues T, Bermejo M, González-Álvarez I, Monteagudo MC, Cabrera-Pérez MÁ. Provisional classification and in silico study of biopharmaceutical system based on caco-2 cell permeability and dose number. Mol Pharm. 2013;10(6):2445-2461.
13. Dahan A, Wolk O, Kim YH, et al. Purely in silico BCS classification: science based quality standards for the world's drugs. Mol Pharm. 2013; 10(11):4378-4390.
14. Lennernäs H, Aarons L, Augustijns P, et al. Oral biopharmaceutics tools - time for a new initiative - an introduction to the IMI project OrBiTo. Eur J Pharm Sci. 2014;16(57):292-299.
15. Fairstein M, Swissa R, Dahan A. Regional-dependent intestinal permeability and BCS classification: elucidation of pH-related complexity in rats using pseudoephedrine. AAPS J. 2013;15(2):589-597.
16. 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):2009-2016.
17. 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): 581-590.
18. 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):388-391.
19. Lennernäs H. Human intestinal permeability. J Pharm Sci. 1998;87(4): 403-410.
20. Lennernäs H. Regional intestinal drug permeation: biopharmaceutics and drug development. Eur J Pharm Sci. 2014;16(57):333-341.
21. Lennernäs H. Human in vivo regional intestinal permeability: importance for pharmaceutical drug development. Mol Pharm. 2014;11(1):12-23.
22. Dahan A, Amidon GL. MRP2 mediated drug-drug interaction: indomethacin increases sulfasalazine absorption in the small intestine, potentially decreasing its colonic targeting. Int J Pharm. 2010;386(1-2):216-220.
23. Dahan A, Sabit H, Amidon GL. The H2 receptor antagonist nizatidine is a P-glycoprotein substrate: characterization of its intestinal epithelial cell efflux transport. AAPS J. 2009;11(2):205-213.
24. Dahan A, Sabit H, Amidon GL. Multiple efflux pumps are involved in the transepithelial transport of colchicine: combined effect of P-glycoprotein and multidrug resistance-associated protein 2 leads to decreased intestinal absorption throughout the entire small intestine. Drug Metab Dispos. 2009;37(10):2028-2036.
25. Miller JM, Dahan A, Gupta D, Varghese S, Amidon GL. Enabling the intestinal absorption of highly polar antiviral agents: ion-pair facilitated membrane permeation of zanamivir heptyl ester and guanidino oseltamivir. Mol Pharm. 2010;7(4):1223-1234.
26. Lipinski CA. Drug-like properties and the causes of poor solubility and poor permeability. J Pharmacol Toxicol Methods. 2000;44(1): 235-249.
27. 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.
28. Winiwarter S, Ax F, Lennernäs H, Hallberg A, Pettersson C, Karlén A. Hydrogen bonding descriptors in the prediction of human in vivo intestinal permeability. J Mol Graph Model. 2003;21(4):273-287.
29. Benet LZ, Broccatelli F, Oprea TI. BDDCS applied to over 900 drugs. AAPS J. 2011;13(4):519-547.
30. Hansch C, Leo AJ. Substituent Constants for Correlation Analysis in Chemistry and Biology. New York: Wiley; 1979.
31. Leo AJ. Calculating log Poct from structures. Chemical Reviews. 1993; 93(4):1281-1306.
32. O'Neil MJ, editor. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 13th ed. Rahway (NJ): Merck; 2001.
33. Ghose AK, Crippen GM. Atomic physicochemical parameters for three-dimensional-structure-directed quantitative structure-activity relationships. 2. Modeling dispersive and hydrophobic interactions. J Chem Inf Comput Sci. 1987;27(1):21-35.
34. Wildman SA, Crippen GM. Prediction of physicochemical parameters by atomic contributions. J Chem Inf Comput Sci. 1999;39(5):868-873.
35. Lennernäs H. Intestinal permeability and its relevance for absorption and elimination. Xenobiotica. 2007;37(10-11):1015-1051.
36. Dahan A, Miller JM, Hilfinger JM, et al. High-permeability criterion for BCS classification: segmental/pH dependent permeability considerations. Mol Pharm. 2010;7(5):1827-1834.
37. Regardh CG, Borg KO, Johansson R, Johnsson G, Palmer L. Pharmacokinetic studies on the selective beta1-receptor antagonist metoprolol in man. J Pharmacokinet Biopharm. 1974;2(4):347-364.
38. Zur M, Gasparini M, Wolk O, Amidon GL, Dahan A. The low/high BCS permeability class boundary: physicochemical comparison of metoprolol and labetalol. Mol Pharm. 2014;11(5):1707-1714.
39. Klasco RK, editor. USP DI® Drug Information for the Health Care Professional. Greenwood Village (CO): Thomson Micromedex; 2004.
40. Amidon GL, Williams NA. A solubility equation for non-electrolytes in water. International Journal of Pharmaceutics. 1982;11(3):249-256.
41. Chu XY, Bleasby K, Yabut J, et al. Transport of the dipeptidyl peptidase-4 inhibitor sitagliptin by human organic anion transporter 3, organic anion transporting polypeptide 4C1, and multidrug resistance P-glycoprotein. J Pharmacol Exp Ther. 2007;321(2):673-683.
42. Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH. Differential recognition of beta-lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995; 270(43):25672-25677.
43. Han HK, Rhie JK, Oh DM, et al. CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999;88(3):347-350.
44. Kanai Y, Endou H. Functional properties of multispecific amino acid transporters and their implications to transporter-mediated toxicity. J Toxicol Sci. 2003;28(1):1-17.
45. Friedman DI, Amidon GL. Oral absorption of peptides: influence of pH and inhibitors on the intestinal hydrolysis of leu-enkephalin and analogues. Pharm Res. 1991;8(1):93-96.
46. Amidon GL, Chang M, Fleisher D, Allen R. Intestinal absorption of amino acid derivatives: importance of the free alpha-amino group. J Pharm Sci. 1982;71(10):1138-1141.
47. Dahan A, Khamis M, Agbaria R, Karaman R. Targeted prodrugs in oral drug delivery: the modern molecular biopharmaceutical approach. Expert Opin Drug Deliv. 2012;9(8):1001-1013.
48. Yang, B, Hu Y, Smith DE. Impact of peptide transporter 1 on the intestinal absorption and pharmacokinetics of valacyclovir after oral dose escalation in wild-type and PepT1 knockout mice. Drug Metab Dispos. 2013;41(10):1867-1874.
49. Yang B, Smith DE. Significance of peptide transporter 1 in the intestinal permeability of valacyclovir in wild-type and PepT1 knockout mice. Drug Metab Dispos. 2013;41(3):608-614.
50. Soldner A, Benet LZ, Mutschler E, Christians U. Active transport of the angiotensin-II antagonist losartan and its main metabolite EXP 3174 across MDCK-MDR1 and caco-2 cell monolayers. Br J Pharmacol. 2000;129(6):1235-1243.
51. Weiss J, Sauer A, Divac N, et al. Interaction of angiotensin receptor type 1 blockers with ATP-binding cassette transporters. Biopharm Drug Dispos. 2010;31(2-3):150-161.
52. Broccatelli F, Cruciani G, Benet LZ, Oprea TI. BDDCS class prediction for new molecular entities. Mol Pharm. 2012;9(3):570-580.
53. Incecayir T, Tsume Y, Amidon GL. Comparison of the permeability of metoprolol and labetalol in rat, mouse, and Caco-2 cells: use as a reference standard for BCS classification. Mol Pharm. 2013;10(3): 958-966.
54. Kasim NA, Whitehouse M, Ramachandran C, et al. Molecular properties of WHO essential drugs and provisional biopharmaceutical classification. Mol Pharm. 2004;1(1):85-96.
55. Takagi T, Ramachandran C, Bermejo M, Yamashita S, Yu LX, Amidon GL. A provisional biopharmaceutical classification of the top 200 oral drug products in the United States, Great Britain, Spain, and Japan. Mol Pharm. 2006;3(6):631-643.
56. Bergström CAS, Norinder U, Luthman K, Artursson P. Molecular descriptors influencing melting point and their role in classification of solid drugs. J Chem Inf Comput Sci. 2003;43(4):1177-1185.
57. Preiss U, Bulut S, Krossing I. In silico prediction of the melting points of ionic liquids from thermodynamic considerations: a case study on 67 salts with a melting point range of 337 degrees C. J Phys Chem B. 2010;114(34):11133-11140.
58. Zhang Y, Maginn EJ. A comparison of methods for melting point calculation using molecular dynamics simulations. J Chem Phys. 2012; 136(14):144116.
59. Wu CY, Benet LZ. Predicting drug disposition via application of BCS: transport/absorption/elimination interplay and development of a biopharmaceutics drug disposition classification system. Pharm Res. 2005;22(1):11-23.
60. Custodio JM, Wu CY, Benet LZ. Predicting drug disposition, absorption/elimination/transporter interplay and the role of food on drug absorption. Adv Drug Deliv Rev. 2008;60(6):717-733.
61. Benet LZ. The role of BCS (biopharmaceutics classification system) and BDDCS (biopharmaceutics drug disposition classification system) in drug development. J Pharm Sci. 2013;102(1):34-42.
62. Dahan A, Beig A, Ioffe-Dahan V, Agbaria R, Miller J. 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 J. 2013;15(2):347-353.
63. Dahan A, Miller JM. The solubility-permeability interplay and its implications in formulation design and development for poorly soluble drugs. AAPS J. 2012;14(2):244-251.
64. Morgen M, Bloom C, Beyerinck R, et al. Polymeric nanoparticles for increased oral bioavailability and rapid absorption using celecoxib as a model of a low-solubility, high-permeability drug. Pharm Res. 2012; 29(2):427-440.
65. 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(2):386-391.
66. Miller JM, Beig A, Krieg BJ, 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): 1848-1856.
67. Dahan A, Hoffman A. Use of a dynamic in vitro lipolysis model to rationalize oral formulation development for poor water soluble drugs: Correlation with in vivo data and the relationship to intra-enterocyte processes in rats. Pharm Res. 2006;23(9):2165-2174.
68. Dahan A, Hoffman A. The effect of different lipid based formulations on the oral absorption of lipophilic drugs: the ability of in vitro lipolysis and consecutive ex vivo intestinal permeability data to predict in vivo bioavailability in rats. Eur J Pharm Biopharm. 2007;67(1):96-105.
69. 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.
70. Koga K, Takarada N, Takada K. Nano-sized water-in-oil-in-water emulsion enhances intestinal absorption of calcein, a high solubility and low permeability compound. Eur J Pharm Biopharm. 2010;74(2): 223-232.
71. Beig A, Agbaria R, Dahan A. Oral delivery of lipophilic drugs: the tradeoff between solubility increase and permeability decrease when using cyclodextrin-based formulations. PLoS One. 2013;8(7):e68237.
72. Beig A, Miller JM, Dahan A. The interaction of nifedipine with selected cyclodextrins and the subsequent solubility-permeability trade-off. Eur J Pharm Biopharm. 2013;85(3):1293-1299.
73. 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):2739-2749.
74. 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):31-37.
75. Sharma P, Varma MV, Chawla HP, Panchagnula R. In situ and in vivo efficacy of peroral absorption enhancers in rats and correlation to in vitro mechanistic studies. Farmaco. 2005;60(11-12):874-883.
76. Sun J, Dahan A, Amidon GL. Enhancing the intestinal absorption of molecules containing the polar guanidino functionality: a double-targeted prodrug approach. J Med Chem. 2010;53(2):624-632.
77. Gupta D, Varghese Gupta S, Dahan A, et al. Increasing oral absorption of polar neuraminidase inhibitors: a prodrug transporter approach applied to oseltamivir analogue. Mol Pharm. 2013;10(2):512-522.
78. Varghese Gupta S, Gupta D, Sun J, et al. Enhancing the intestinal membrane permeability of zanamivir: a carrier mediated prodrug approach. Mol Pharm. 2011;8(6):2358-2367.
79. Radwan A, Amidon GL, Langguth P. Mechanistic investigation of food effect on disintegration and dissolution of BCS class III compound solid formulations: the importance of viscosity. Biopharm Drug Dispos. 2012; 33(7):403-416.
80. Dahan A, Duvdevani R, Shapiro I, Elmann A, Finkelstein E, Hoffman A. The oral absorption of phospholipid prodrugs: in vivo and in vitro mechanistic investigation of trafficking of a lecithin-valproic acid conjugate following oral administration. J Control Release. 2008; 126(1):1-9.