Drug precipitation inhibitors in supersaturable formulations

International Journal of Pharmaceutics

Volumn 453, Issue 1, 2013, Pages 36-43

  Xua, Sen ^a   Dai, Wei Guo ^b  

^a Drexel University   (United States)

^b JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

Author keywords

Bioavailability; Drug precipitation; Poorly water soluble compounds; Precipitation inhibitors; Supersaturable formulations

Indexed keywords

ALBENDAZOLE SULFOXIDE; BUTYL PARABEN; CARBAMAZEPINE; CELECOXIB; CELLULOSE DERIVATIVE; CYCLODEXTRIN; DODECYL SULFATE SODIUM; HYDROXYPROPYLMETHYLCELLULOSE; HYDROXYPROPYLMETHYLCELLULOSE ACETATE SUCCINATE; INDIRUBIN; ITRACONAZOLE; MACROGOL 6000; MACROGOL DERIVATIVE; METHYLCELLULOSE; PACLITAXEL; POLOXAMER; POLYVINYL ALCOHOL; POVIDONE; SALBUTAMOL SULFATE; SAQUINAVIR; TACROLIMUS;

ATOMIC FORCE MICROSCOPY; CRITICAL MICELLE CONCENTRATION; CRYSTAL STRUCTURE; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DOG; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG SOLUBILITY; DRUG SOLUTION; GASTROINTESTINAL TRACT; HYDROGEN BOND; HYDROPHOBICITY; IN VITRO STUDY; IN VIVO STUDY; INFRARED SPECTROSCOPY; INTESTINE FLUID; MICROFLUIDICS; MOLECULAR WEIGHT; NONHUMAN; PARTICLE SIZE; PHYSICAL CHEMISTRY; PRECIPITATION; PRIORITY JOURNAL; RAMAN SPECTROMETRY; REVIEW; SCANNING ELECTRON MICROSCOPE; STEREOSPECIFICITY; STOMACH JUICE; THERMODYNAMICS; VISCOSITY; WETTABILITY; X RAY DIFFRACTION; X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 84884167268     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2013.05.013     Document Type: Review

References (84)

1. Agüeros, M., Zabaleta, V., Espuelas, S., Campanero, M.A., Irache, J.M., 2010. Increased oral bioavailability of paclitaxel by its encapsulation through complex formation with cyclodextrins in poly(anhydride) nanoparticles. J. Control. Release 145, 2-8.
2. Anby, M.U., Williams, H.D., McIntosh, M., Benameur, H., Edwards, G.A., Pouton, C.W., Porter, C.J.H., 2012. Lipid digestion as a trigger for supersaturation: evaluation of the impact of supersaturation stabilization on the in vitro and in vivo performance of self-emulsifying drug delivery systems. Mol. Pharm. 9, 2063-2079.
3. Balani, P.N., Wong, S.Y., Ng, W.K., Widjaja, E., Tan, R.B.H., Chan, S.Y., 2010. Influence of polymer content on stabilizing milled amorphous salbutamol sulphate. Int. J. Pharm. 391, 125-136.
4. Bevernage, J., Forier, T., Brouwers, J., Tack, J., Annaert, P., Augustijns, P., 2011. Excipient-mediated supersaturation stabilization in human intestinal fluids. Mol. Pharm. 8, 564-570.
5. Bevernage, J., Hens, B., Brouwers, J., Tack, J., Annaert, P., Augustijns, P., 2012. Supersaturation in human gastric fluids. Eur. J. Pharm. Biopharm. 81, 184-189.
6. Bi, M., Kyad, A., Kiang, Y.-H., Alvarez-Nunez, F., Alvarez, F., 2011. Enhancing and sustaining AMG 009 dissolution from a matrix tablet via microenvironmental pH modulation and supersaturation. AAPS PharmSciTech 12, 1157-1162.
7. Brewster, M.E., Vandecruys, R., Peeters, J., Neeskens, P., Verreck, G., Loftsson, T., 2008. Comparative interaction of 2-hydroxypropyl-β- cyclodextrin and sulfobutylether-β-cyclodextrin with itraconazole: phase-solubility behavior and stabilization of supersaturated drug solutions. Eur. J. Pharm. Sci. 34, 94-103.
8. Brouwers, J., Brewster, M.E., Augustijns, P., 2009. Supersaturating drug delivery systems: the answer to solubility-limited oral bioavailability?? J. Pharm. Sci. 98, 2549-2572.
9. Brouwers, J., Vermeire, K., Grammen, C., Schols, D., Augustijns, P., 2011. Early identification of availability issues for poorly water-soluble microbicide candidates in biorelevant media: a case study with saquinavir. Antiviral Res. 91, 217-223.
10. Burda, C., Chen, X., Narayanan, R., El-Sayed, M.A., 2005. Chemistry and properties of nanocrystals of different shapes. Chem. Rev. 105, 1025-1102. (Pubitemid 40600877)
11. Chauhan, H., Hui-Gu, C., Atef, E., 2013. Correlating the behavior of polymers in solution as precipitation inhibitor to its amorphous stabilization ability in solid dispersions. J. Pharm. Sci. 102, 1924-1935.
12. Chen, Z.Q., Liu, Y., Zhao, J.H., Wang, L., Feng, N.P., 2012. Improved oral bioavailability of poorly water-soluble indirubin by a supersaturatable self-microemulsifying drug delivery system. Int. J. Nanomed. 7, 1115-1125.
13. Curatolo, W., Nightingale, J., Herbig, S., 2009. Utility of hydroxypropylmethylcellulose acetate succinate (HPMCAS) for initiation and maintenance of drug supersaturation in the GI milieu. Pharm. Res. 26, 1419-1431.
14. Dai, W.G., 2010. In vitro methods to assess drug precipitation. Int. J. Pharm. 393, 1-16.
15. Dai, W.G., Dong, L.C., Li, S., Deng, Z.Y., 2008. Combination of pluronic/vitamin E TPGS as a potential inhibitor of drug precipitation. Int. J. Pharm. 355, 31-37.
16. Dai, W.G., Dong, L.C., Shi, X., Nguyen, J., Evans, J., Xu, Y., Creasey, A.A., 2007a. Evaluation of drug precipitation of solubility-enhancing liquid formulations using milligram quantities of a new molecular entity (NME). J. Pharm. Sci. 96, 2957-2969. (Pubitemid 350221196)
17. Dai, W.G., Dong, L.C., Song, Y.Q., 2007b. Nanosizing of a drug/carrageenan complex to increase solubility and dissolution rate. Int. J. Pharm. 342, 201-207. (Pubitemid 47259320)
18. Dai, W.G., Liang, C.D., Creasey, A.A., 2011. Inhibiting the precipitation of poorly water-soluble drugs from labrasol formulations. Pharm. Technol. 35, 50-54.
19. Dias, M.M.R., Raghavan, S.L., Pellett, M.A., Hadgraft, J., 2003. The effect of β-cyclodextrins on the permeation of diclofenac from supersaturated solutions. Int. J. Pharm. 263, 173-181. (Pubitemid 37087944)
20. DiNunzio, J.C., Hughey, J.R., Brough, C., Miller, D.A., Williams III, R.O., McGinity, J.W., 2010. Production of advanced solid dispersions for enhanced bioavailability of itraconazole using KinetiSol® dispersing. Drug Dev. Ind. Pharm. 36, 1064-1078.
21. DiNunzio, J.C., Miller, D.A., Yang, W., McGinity, J.W., Williams, R.O., 2008. Amorphous compositions using concentration enhancing polymers for improved bioavailability of itraconazole. Mol. Pharm. 5, 968-980.
22. Douroumis, D., Fahr, A., 2007. Stable carbamazepine colloidal systems using the cosolvent technique. Eur. J. Pharm. Sci. 30, 367-374. (Pubitemid 46436452)
23. Edwards, F., Tsakmaka, C., Mohr, S., Fielden, P.R., Goddard, N.J., Booth, J., Tam, K.Y., 2013. Using droplet-based microfluidic technology to study the precipitation of a poorly water-soluble weakly basic drug upon a pH-shift. Analyst 138, 339-345.
24. Engers, D., Teng, J., Jimenez-Novoa, J., Gent, P., Hossack, S., Campbell, C., Thomson, J., Ivanisevic, I., Templeton, A., Byrn, S., Newman, A., 2010. A solid-state approach to enable early development compounds: selection and animal bioavailability studies of an itraconazole amorphous solid dispersion. J. Pharm. Sci. 99, 3901-3922.
25. Erdemir, D., Lee, A.Y., Myerson, A.S., 2009. Nucleation of crystals from solution: classical and two-step models. Acc. Chem. Res. 42, 621-629.
26. Friesen, D.T., Shanker, R., Crew, M., Smithey, D.T., Curatolo, W.J., Nightingale, J.A.S., 2008. Hydroxypropyl methylcellulose acetate succinate-based spray-dried dispersions: an overview. Mol. Pharm. 5, 1003-1019.
27. Gao, P., Akrami, A., Alvarez, F., Hu, J., Li, L., Ma, C., Surapaneni, S., 2009. Characterization and optimization of AMG 517 supersaturatable self-emulsifying drug delivery system (S-SEDDS) for improved oral absorption. J. Pharm. Sci. 98, 516-528.
28. Gao, P., Guyton, M.E., Huang, T.H., Bauer, J.M., Stefanski, K.J., Lu, Q., 2004. Enhanced oral bioavailability of a poorly water soluble drug PNU-91325 by supersaturatable formulations. Drug Dev. Ind. Pharm. 30, 221-229. (Pubitemid 38420267)
29. Gao, P., Rush, B.D., Pfund, W.P., Huang, T.H., Bauer, J.M., Morozowich, W., Kuo, M.S., Hageman, M.J., 2003. Development of a supersaturable SEDDS (S-SEDDS) formulation of paclitaxel with improved oral bioavailability. J. Pharm. Sci. 92, 2386-2398. (Pubitemid 37484765)
30. Gao, P., Shi, Y., 2012. Characterization of supersaturatable formulations for improved absorption of poorly soluble drugs. AAPS J. 14, 703-713.
31. Garekani, H.A., Ford, J.L., Rubinstein, M.H., Rajabi-Siahboomi, A.R., 2000. Highly compressible paracetamol. I. Crystallization and characterization. Int. J. Pharm. 208, 87-99.
32. Ghosh, I., Snyder, J., Vippagunta, R., Alvine, M., Vakil, R., Tong, W.-Q., Vippagunta, S., 2011. Comparison of HPMC based polymers performance as carriers for manufacture of solid dispersions using the melt extruder. Int. J. Pharm. 419, 12-19.
33. Gosangari, S., Dyakonov, T., 2013. Enhanced dissolution performance of curcumin with the use of supersaturatable formulations. Pharm. Dev. Technol. 18, 475-480.
34. Guzman, H.R., Tawa, M., Zhang, Z., Ratanabanangkoon, P., Shaw, P., Gardner, C.R., Chen, H., Moreau, J.P., Almarsson, O., Remenar, J.F., 2007. Combined use of crystalline salt forms and precipitation inhibitors to improve oral absorption of celecoxib from solid oral formulations. J. Pharm. Sci. 96, 2686-2702. (Pubitemid 47597818)
35. Han, H.-K., Lee, B.-J., Lee, H.-K., 2011. Enhanced dissolution and bioavailability of biochanin A via the preparation of solid dispersion: in vitro and in vivo evaluation. Int. J. Pharm. 415, 89-94.
36. Iervolino, M., Raghavan, S.L., Hadgraft, J., 2000. Membrane penetration enhancement of ibuprofen using supersaturation. Int. J. Pharm. 198, 229-238. (Pubitemid 30184859)
37. Ilevbare, G.A., Liu, H., Edgar, K.J., Taylor, L.S., 2012a. Maintaining supersaturation in aqueous drug solutions: impact of different polymers on induction times. Cryst. Growth Des. 13, 740-751.
38. Ilevbare, G.A., Liu, H., Edgar, K.J., Taylor, L.S., 2012b. Understanding polymer properties important for crystal growth inhibition-impact of chemically diverse polymers on solution crystal growth of ritonavir. Cryst. Growth Des. 12, 3133-3143.
39. Kashchiev, D., van Rosmalen, G.M., 2003. Review: nucleation in solutions revisited. Cryst. Res. Technol. 38, 555-574.
40. Kataoka, M., Sugano, K., Mathews, C., Wong, J., Jones, K., Masaoka, Y., Sakuma, S., Yamashita, S., 2012. Application of dissolution/permeation system for evaluation of formulation effect on oral absorption of poorly water-soluble drugs in drug development. Pharm. Res. 29, 1485-1494.
41. Kestur, U.S., Lee, H., Santiago, D., Rinaldi, C., Won, Y.-Y., Taylor, L.S., 2010. Effects of the molecular weight and concentration of polymer additives, and temperature on the melt crystallization kinetics of a small drug molecule. Cryst. Growth Des. 10, 3585-3595.
42. Kim, M.-S., Kim, J.-S., Cho, W., Cha, K.-H., Park, H.-J., Park, J., Hwang, S.-J., 2013. Supersaturatable formulations for the enhanced oral absorption of sirolimus. Int. J. Pharm. 445, 108-116.
43. Konno, H., Handa, T., Alonzo, D.E., Taylor, L.S., 2008. Effect of polymer type on the dissolution profile of amorphous solid dispersions containing felodipine. Eur. J. Pharm. Biopharm. 70, 493-499.
44. Kramarenko, E.Y., Winkler, R.G., Khalatur, P.G., Khokhlov, A.R., Reineker, P., 1996. Molecular dynamics simulation study of adsorption of polymer chains with variable degree of rigidity. I. Static properties. J. Chem. Phys. 104, 4806-4813. (Pubitemid 126715655)
45. Lechuga-Ballesteros, D., Rodríguez-Hornedo, N., 1995. The influence of additives on the growth kinetics and mechanism of l-alanine crystals. Int. J. Pharm. 115, 139-149.
46. Leuner, C., Dressman, J., 2000. Improving drug solubility for oral delivery using solid dispersions. Eur. J. Pharm. Biopharm. 50, 47-60. (Pubitemid 30326688)
47. Li, S., Pollock-Dove, C., Dong, L.C., Chen, J., Creasey, A.A., Dai, W.-G., 2012. Enhanced bioavailability of a poorly water-soluble weakly basic compound using a combination approach of solubilization agents and precipitation inhibitors: a case study. Mol. Pharm. 9, 1100-1108.
48. Lindfors, L., Forssén, S., Westergren, J., Olsson, U., 2008. Nucleation and crystal growth in supersaturated solutions of a model drug. J. Colloid Interface Sci. 325, 404-413.
49. Loftsson, T., Brewster, M.E., 1996. Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J. Pharm. Sci. 85, 1017-1025. (Pubitemid 26338912)
50. Loftsson, T., Brewster, M.E., 2012. Cyclodextrins as functional excipients: methods to enhance complexation efficiency. J. Pharm. Sci. 101, 3019-3032.
51. Loftsson, T., Fria??riksd?3ttir, H.n., Gua??mundsd?3ttir, T.r.K., 1996. The effect of water-soluble polymers on aqueous solubility of drugs. Int. J. Pharm. 127, 293-296.
52. Loftsson, T., Vogensen, S.B., Brewster, M.E., Konráosdó ttir, F., 2007. Effects of cyclodextrins on drug delivery through biological membranes. J. Pharm. Sci. 96, 2532-2546. (Pubitemid 47597809)
53. Ma, X., Taw, J., Chiang, C.-M., 1996. Control of drug crystallization in transdermal matrix system. Int. J. Pharm. 142, 115-119. (Pubitemid 26343836)
54. Miller, D.A., DiNunzio, J.C., Yang, W., McGinity, J.W., Williams, R.O., 2008. Enhanced in vivo absorption of itraconazole via stabilization of supersaturation following acidic-to-neutral pH transition. Drug Dev. Ind. Pharm. 34, 890-902.
55. Morgen, M., Bloom, C., Beyerinck, R., Bello, A., Song, W., Wilkinson, K., Steenwyk, R., Shamblin, S., 2012. Polymeric nanoparticles for increased oral bioavailability and rapid absorption using celecoxib as a model of a low-solubility, high-permeability drug. Pharm. Res. 29, 427-440.
56. Overhoff, K.A., McConville, J.T., Yang, W., Johnston, K.P., Peters, J.I., Williams, R.O., 2008. Effect of stabilizer on the maximum degree and extent of supersaturation and oral absorption of tacrolimus made by ultra-rapid freezing. Pharm. Res. 25, 167-175.
57. Palermo, R., Anderson, C., Drennen III, J., 2012. Review: use of thermal, diffraction, and vibrational analytical methods to determine mechanisms of solid dispersion stability. J. Pharm. Innov. 7, 2-12.
58. Plaizier-Vercammen, J.A., 1983. Interaction of povidone with aromatic compounds IV: effects of macromolecule molecular weight, solvent dielectric constant, and ligand solubility on complex formation. J. Pharm. Sci. 72, 1042-1044.
59. Pouton, C.W., 2000. Lipid formulations for oral administration of drugs: non-emulsifying, self-emulsifying and 'self-microemulsifying' drug delivery systems. Eur. J. Pharm. Sci. 11, S93-S98.
60. Pouton, C.W., 2006. Formulation of poorly water-soluble drugs for oral administration: physicochemical and physiological issues and the lipid formulation classification system. Eur. J. Pharm. Sci. 29, 278-287. (Pubitemid 44740131)
61. Pouton, C.W., Porter, C.J.H., 2008. Formulation of lipid-based delivery systems for oral administration: materials, methods and strategies. Adv. Drug Del. Rev. 60, 625-637.
62. Qian, F., Wang, J., Hartley, R., Tao, J., Haddadin, R., Mathias, N., Hussain, M., 2012. Solution behavior of PVP-VA and HPMC-AS-based amorphous solid dispersions and their bioavailability implications. Pharm. Res. 29, 2766-2776.
63. Raghavan, S.L., Trividic, A., Davis, A.F., Hadgraft, J., 2001. Crystallization of hydrocortisone acetate: influence of polymers. Int. J. Pharm. 212, 213-221. (Pubitemid 32119447)
64. Rasenack, N., Hartenhauer, H., Müller, B.W., 2003. Microcrystals for dissolution rate enhancement of poorly water-soluble drugs. Int. J. Pharm. 254, 137-145. (Pubitemid 36298822)
65. Serajuddin, A.T.M., 1999. Solid dispersion of poorly water-soluble drugs: early promises, subsequent problems, and recent breakthroughs. J. Pharm. Sci. 88, 1058-1066.
66. Simonelli, A.P., Mehta, S.C., Higuchi, W.I., 1970. Inhibition of sulfathiazole crystal growth by polyvinylpyrrolidone. J. Pharm. Sci. 59, 633-638.
67. Tajarobi, F., Larsson, A., Matic, H., Abrahmsén-Alami, S., 2011. The influence of crystallization inhibition of HPMC and HPMCAS on model substance dissolution and release in swellable matrix tablets. Eur. J. Pharm. Biopharm. 78, 125-133.
68. Tian, F., Saville, D.J., Gordon, K.C., Strachan, C.J., Zeitler, J.A., Sandler, N., Rades, T., 2007. The influence of various excipients on the conversion kinetics of carbamazepine polymorphs in aqueous suspension. J. Pharm. Pharmacol. 59, 193-201. (Pubitemid 46203058)
69. Trasi, N.S., Taylor, L.S., 2012. Effect of additives on crystal growth and nucleation of amorphous flutamide. Cryst. Growth Des. 12, 3221-3230.
70. Usui, F., Maeda, K., Kusai, A., Nishimura, K., Keiji, Y., 1997. Inhibitory effects of water-soluble polymers on precipitation of RS-8359. Int. J. Pharm. 154, 59-66. (Pubitemid 27326820)
71. Van Speybroeck, M., Mols, R., Mellaerts, R., Thi, T.D., Martens, J.A., Humbeeck, J.V., Annaert, P., Mooter, G.V.d., Augustijns, P., 2010. Combined use of ordered mesoporous silica and precipitation inhibitors for improved oral absorption of the poorly soluble weak base itraconazole. Eur. J. Pharm. Biopharm. 75, 354-365.
72. Verma, S., Huey, B.D., Burgess, D.J., 2009. Scanning probe microscopy method for nanosuspension stabilizer selection. Langmuir 25, 12481-12487.
73. Vetter, T., Mazzotti, M., Brozio Jr., 2011. Slowing the growth rate of ibuprofen crystals using the polymeric additive Pluronic F127. Cryst. Growth Des. 11, 3813-3821.
74. Warren, D.B., Benameur, H., Porter, C.J.H., Pouton, C.W., 2010. Using polymeric precipitation inhibitors to improve the absorption of poorly water-soluble drugs: a mechanistic basis for utility. J. Drug Target. 18, 704-731.
75. Wei, Y., Ye, X., Shang, X., Peng, X., Bao, Q., Liu, M., Guo, M., Li, F., 2012. Enhanced oral bioavailability of silybin by a supersaturatable self-emulsifying drug delivery system (S-SEDDS). Colloids Surf. A 396, 22-28.
76. Won, D.-H., Kim, M.-S., Lee, S., Park, J.-S., Hwang, S.-J., 2005. Improved physico-chemical characteristics of felodipine solid dispersion particles by supercritical anti-solvent precipitation process. Int. J. Pharm. 301, 199-208. (Pubitemid 41206604)
77. Wu, Z., Tucker, I.G., Razzak, M., Yang, L., McSporran, K., Medlicott, N.J., 2010. Absorption and tissue tolerance of ricobendazole in the presence of hydroxypropyl-β-cyclodextrin following subcutaneous injection in sheep. Int. J. Pharm. 397, 96-102.
78. Xie, S., Poornachary, S.K., Chow, P.S., Tan, R.B.H., 2010. Direct precipitation of micronsize salbutamol sulfate: new insights into the action of surfactants and polymeric additives. Cryst. Growth Des. 10, 3363-3371.
79. Yamashita, K., Nakate, T., Okimoto, K., Ohike, A., Tokunaga, Y., Ibuki, R., Higaki, K., Kimura, T., 2003. Establishment of new preparation method for solid dispersion formulation of tacrolimus. Int. J. Pharm. 267, 79-91. (Pubitemid 37352952)
80. Yang, W., Johnston, K.P., Williams Iii, R.O., 2010. Comparison of bioavailability of amorphous versus crystalline itraconazole nanoparticles via pulmonary administration in rats. Eur. J. Pharm. Biopharm. 75, 33-41.
81. Yani, Y., Chow, P.S., Tan, R.B.H., 2011. Molecular simulation study of the effect of various additives on salbutamol sulfate crystal habit. Mol. Pharm. 8, 1910-1918.
82. Zhang, N., Zhang, W., Jin, Y., Quan, D.-Q., 2011. Studies on preparation of carbamazepine (CBZ) supersaturatable self-microemulsifying (S-SMEDDS) formulation and relative bioavailability in beagle dogs. Pharm. Dev. Technol. 16, 415-421.
83. Ziller, K.H., Rupprecht, H., 1988. Conteol of crystal growth in drug suspensions: (1 design of a conteol unit and application to acetaminophen suspensions). Drug Dev. Ind. Pharm. 14, 2341-2370.
84. Zimmermann, A., Millqvist-Fureby, A., Elema, M.R., Hansen, T., Müllertz, A., Hovgaard, L., 2009. Adsorption of pharmaceutical excipients onto microcrystals of siramesine hydrochloride: effects on physicochemical properties. Eur. J. Pharm. Biopharm. 71, 109-116.