Improving Oral Bioavailability of Sorafenib by Optimizing the "spring" and "parachute" Based on Molecular Interaction Mechanisms

Molecular Pharmaceutics

Volumn 13, Issue 2, 2016, Pages 599-608

  Liu, Chengyu ^a   Chen, Zhen ^a   Chen, Yuejie ^a   Lu, Jia ^b   Li, Yuan ^b   Wang, Shujing ^a   Wu, Guoliang ^a   Qian, Feng ^a  

^a TSINGHUA UNIVERSITY   (China)

^b SOOCHOW UNIVERSITY   (China)

Author keywords

bioavailability; molecular interaction; polymer surfactant complex; poorly water soluble drugs; sorafenib

Indexed keywords

DODECYL SULFATE SODIUM; POLY(VINYLPYRROLIDONE VINYL ACETATE); POLYMER; SORAFENIB; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; CARBANILAMIDE DERIVATIVE; NICOTINAMIDE; TABLET;

AREA UNDER THE CURVE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CRYSTALLIZATION; DRUG BIOAVAILABILITY; DRUG SOLUBILITY; IN VITRO STUDY; INFRARED SPECTROSCOPY; MAXIMUM PLASMA CONCENTRATION; MICELLIZATION; MOLECULAR INTERACTION; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; TABLET; TABLET FORMULATION; ANALOGS AND DERIVATIVES; ANIMAL; BIOAVAILABILITY; CHEMISTRY; DOG; MALE; MEDICINAL CHEMISTRY; ORAL DRUG ADMINISTRATION; SOLUBILITY; TISSUE DISTRIBUTION;

ADMINISTRATION, ORAL; ANIMALS; ANTINEOPLASTIC AGENTS; BIOLOGICAL AVAILABILITY; CHEMISTRY, PHARMACEUTICAL; DOGS; MALE; NIACINAMIDE; PHENYLUREA COMPOUNDS; POLYMERS; SOLUBILITY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TABLETS; TISSUE DISTRIBUTION;

EID: 84957309260     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/acs.molpharmaceut.5b00837     Document Type: Article

References (34)

1. Wilhelm, S.; Carter, C.; Lynch, M.; Lowinger, T.; Dumas, J.; Smith, R. A.; Schwartz, B.; Simantov, R.; Kelley, S. Discovery and development of sorafenib: a multikinase inhibitor for treating cancer Nat. Rev. Drug Discovery 2006, 5 (10) 835-44 10.1038/nrd2130
2. Liu, L.; Cao, Y.; Chen, C.; Zhang, X.; McNabola, A.; Wilkie, D.; Wilhelm, S.; Lynch, M.; Carter, C. Sorafenib blocks the RAF/MEK/ERK pathway, inhibits tumor angiogenesis, and induces tumor cell apoptosis in hepatocellular carcinoma model PLC/PRF/5 Cancer Res. 2006, 66 (24) 11851-8 10.1158/0008-5472.CAN-06-1377
3. Wilhelm, S. M.; Adnane, L.; Newell, P.; Villanueva, A.; Llovet, J. M.; Lynch, M. Preclinical overview of sorafenib, a multikinase inhibitor that targets both Raf and VEGF and PDGF receptor tyrosine kinase signaling Mol. Cancer Ther. 2008, 7 (10) 3129-40 10.1158/1535-7163.MCT-08-0013
4. Smalley, K. S.; Xiao, M.; Villanueva, J.; Nguyen, T. K.; Flaherty, K. T.; Letrero, R.; Van Belle, P.; Elder, D. E.; Wang, Y.; Nathanson, K. L.; Herlyn, M. CRAF inhibition induces apoptosis in melanoma cells with non-V600E BRAF mutations Oncogene 2009, 28 (1) 85-94 10.1038/onc.2008.362
5. US Food and Drug Administration. Sorafenib (Nexavar) prescribing information (2005).
6. Llovet, J. M.; Ricci, S.; Mazzaferro, V.; Hilgard, P.; Gane, E.; Blanc, J.-F. Sorafenib in Advanced Hepatocellular Carcinoma N. Engl. J. Med. 2008, 359, 378-390 10.1056/NEJMoa0708857
7. Nexavar: European Public Assessment Reports (EPAR)-Scientific Discussion. European Medicines Agency (EMA). Available at http://www.ema.europa.eu/docs/en-GB/document-library/EPAR-Scientific-Discussion/human/000690/WC500027707.pdf.
8. 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 10.1023/A:1016212804288
9. Gongora, C. Sorafenib inhibits ABCG2 and overcomes irinotecan resistance - response Mol. Cancer Ther. 2014, 13 (3) 764 10.1158/1535-7163.MCT-13-1026
10. Zhang, L.; Xia, W.; Wang, B.; Luo, Y.; Lu, W. Convenient Synthesis of Sorafenib and Its Derivatives Synth. Commun. 2011, 41 (21) 3140-3146 10.1080/00397911.2010.517372
11. Lind, J. S. W. et al. A multicenter phase II study of erlotinib and sorafenib in chemotherapy-naive patients with advanced non-small cell lung cancer Clin. Cancer Res. 2010, 16, 3078-3087 10.1158/1078-0432.CCR-09-3033
12. Bock, C.; Lengauer, T. Managing drug resistance in cancer: lessons from HIV therapy Nat. Rev. Cancer 2012, 12 (7) 494-501 10.1038/nrc3297
13. Serajuddin, A. T. Salt formation to improve drug solubility Adv. Drug Delivery Rev. 2007, 59 (7) 603-16 10.1016/j.addr.2007.05.010
14. Stella, V. J.; Nti-Addae, K. W. Prodrug strategies to overcome poor water solubility Adv. Drug Delivery Rev. 2007, 59 (7) 677-94 10.1016/j.addr.2007.05.013
15. Müller, R. H.; Peters, K. Nanosuspensions for the formulation of poorly soluble drugs I. Preparation by a size-reduction technique Int. J. Pharm. 1998, 160, 229-237 10.1016/S0378-5173(97)00311-6
16. Shegokar, R.; Muller, R. H. Nanocrystals: industrially feasible multifunctional formulation technology for poorly soluble actives Int. J. Pharm. 2010, 399 (1-2) 129-39 10.1016/j.ijpharm.2010.07.044
17. Yalkowsky, S. H. Solubility and solubilization in aqueous media; Oxford University Press: New York, 1999.
18. Sethia, S.; Squillante, E. Solid dispersions: revival with greater possibilities and applications in oral drug delivery Crit. Rev. Ther. Drug Carrier Syst. 2003, 20, 215-247 10.1615/CritRevTherDrugCarrierSyst.v20.i23.40
19. Vasconcelos, T.; Sarmento, B.; Costa, P. Solid dispersions as strategy to improve oral bioavailability of poor water soluble drugs Drug Discovery Today 2007, 12 (23-24) 1068-75 10.1016/j.drudis.2007.09.005
20. Brouwers, J.; Brewster, M. E.; Augustijns, P. Supersaturating drug delivery systems: the answer to solubility-limited oral bioavailability? J. Pharm. Sci. 2009, 98 (8) 2549-72 10.1002/jps.21650
21. Ilevbare, G. A.; Liu, H.; Edgar, K. J.; Taylor, L. S. Maintaining Supersaturation in Aqueous Drug Solutions: Impact of Different Polymers on Induction Times Cryst. Growth Des. 2013, 13 (2) 740-751 10.1021/cg301447d
22. Ueda, K.; Higashi, K.; Yamamoto, K.; Moribe, K. Inhibitory Effect of Hydroxypropyl Methylcellu lose Acetate Succinate on Drug Recrystallization from a Supersaturated Solution Assessed Using Nuclear Magnetic Resonance Measurements Mol. Pharmaceutics 2013, 10 (10) 3801-3811 10.1021/mp400278j
23. Konno, H.; Handa, T.; Alonzo, D. E.; Taylor, L. S. Effect of polymer type on the dissolution profile of amorphous solid dispersions containing felodipine Eur. J. Pharm. Biopharm. 2008, 70 (2) 493-499 10.1016/j.ejpb.2008.05.023
24. Guzman, H. R.; Tawa, M.; Zhang, Z.; Ratanabanangkoon, P.; Shaw, P.; Gardner, C. R.; Chen, H.; Moreau, J. P.; Almarsson, O.; Remenar, J. F. Combined use of crystalline salt forms and precipitation inhibitors to improve oral absorption of celecoxib from solid oral formulations J. Pharm. Sci. 2007, 96 (10) 2686-702 10.1002/jps.20906
25. Chen, Y.; Liu, C.; Chen, Z.; Su, C.; Hageman, M.; Hussain, M.; Haskell, R.; Stefanski, K.; Qian, F. Drug-polymer-water interaction and its implication for the dissolution performance of amorphous solid dispersions Mol. Pharmaceutics 2015, 12 (2) 576-89 10.1021/mp500660m
26. Ioakimidis, L.; Thoukydidis, L.; Mirza, A.; Naeem, S.; Reynisson, J. Benchmarking the Reliability of QikProp. Correlation between Experimental and Predicted Values QSAR Comb. Sci. 2008, 27 (4) 445-456 10.1002/qsar.200730051
27. Yu, L. X.; Carlin, A. S.; Amidon, G. L.; Hussain, A. S. Feasibility studies of utilizing disk intrinsic dissolution rate to classify drugs Int. J. Pharm. 2004, 270 (1-2) 221-227 10.1016/j.ijpharm.2003.10.016
28. Wood, J. H.; Syarto, J. E.; Letterman, H. Improved holder for intrinsic dissolution rate studies J. Pharm. Sci. 1965, 54, 1068 10.1002/jps.2600540730
29. Chari, K.; Lenhart, W. C. Effect of Polyvinylpyrrolidone on the Self-Assembly of Model Hydrocarbon Amphiphiles J. Colloid Interface Sci. 1989, 137 (1) 204-216 10.1016/0021-9797(90)90057-U
30. Macomber, R. S. A complete introduction to modern NMR spectroscopy; John Wiley & Sons, Ltd.: 1998.
31. Roscigno, P.; Asaro, F.; Pellizer, G.; Ortona, O.; Paduano, L. Complex Formation between Poly(vinylpyrrolidone) and Sodium Decyl Sulfate Studied through NMR Langmuir 2003, 19, 9638-9644 10.1021/la034928r
32. Anwar, J.; Boateng, P. K.; Tamaki, R.; Odedra, S. Mode of action and design rules for additives that modulate crystal nucleation Angew. Chem., Int. Ed. 2009, 48 (9) 1596-600 10.1002/anie.200804553
33. Qi, S.; Roser, S.; Edler, K. J.; Pigliacelli, C.; Rogerson, M.; Weuts, I.; Van Dycke, F.; Stokbroekx, S. Insights into the role of polymer-surfactant complexes in drug solubilisation/stabilisation during drug release from solid dispersions Pharm. Res. 2013, 30 (1) 290-302 10.1007/s11095-012-0873-7
34. Kwak, J. C. T., Ed. Polymer-surfactant systems; Marcel Dekker, Inc.: New York, 1998.