Liquid anti-solvent recrystallization to enhance dissolution of CRS 74, a new antiretroviral drug

References

• Lipp R. The Innovator pipeline: bioavailability challenges and advanced oral drug delivery opportunities. Am Pharm Rev 2013;16:14–16
   Google Scholar
• 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;11:740–6
   PubMed Web of Science ®Google Scholar
• Woodahl EL, Yang Z, Bui T, et al. MDR1 G1199A polymorphism alters permeability of HIV protease inhibitors across P-glycoprotein-expressing epithelial cells. AIDS 2005;19:1617–25
   PubMed Web of Science ®Google Scholar
• Holmstock N, Annaert P, Augustijns P. Boosting of HIV protease inhibitors by ritonavir in the intestine: the relative role of cytochrome P450 and P-glycoprotein inhibition based on Caco-2 monolayers versus in situ intestinal perfusion in mice. Drug Metab Dispos 2012;40:1473–77
   PubMed Web of Science ®Google Scholar
• Barry M, Mulcahy F, Merry C, et al. Pharmacokinetics and potential interactions amongst antiretroviral agents used to treat patients with HIV infection. Clin Pharmacokinet 1999;36:289–304
   PubMed Web of Science ®Google Scholar
• Pulido F, Matarranz M, Rodríguez-Rivera V, et al. Boosted protease inhibitor monotherapy: what have we learnt after seven years of research? AIDS Rev 2010;12:127–34
   PubMed Web of Science ®Google Scholar
• De Clercq E. Dancing with chemical formulae of antivirals: a panoramic view (Part 2). Biochem Pharmacol 2013;86:1397–410
   PubMed Web of Science ®Google Scholar
• Bockelmann MA, Rosatto SS, Fuzeto CR, et al. Ritonavir analogous compound useful as retroviral protease inhibitor, preparation of the ritonavir analogous compound and pharmaceutical composition for the ritonavir analogous compound. European Patent, WO 2005/111006 2005
   Google Scholar
• Bockelmann MA, Rosatto SS, Fuzeto CR, et al. Ritonavir analogous compound useful as retroviral protease inhibitor, preparation of the ritonavir analogous compound and pharmaceutical composition for the ritonavir analogous compound. United States patent 7763733 2010
   Google Scholar
• Max B, Sherer R. Management of the adverse effects of antiretroviral therapy and medication adherence. Clin Infect Dis 2000;2:96–116
   Google Scholar
• Rodríguez-Spong B, Price CP, Jayasankar A, et al. General principles of polymorphism: a supramolecular perspective. Adv Drug Deliv Rev 2004;56:241–74
   PubMed Web of Science ®Google Scholar
• Giulietti M, Seckler MM, Derenzo S, et al. Industrial crystallization and precipitation from solutions: state of the technique. Braz J Chem Eng 2001;18:423–40
   Web of Science ®Google Scholar
• Azad MA, Knieke C, To D, Davé R. Preparation of concentrated stable fenofibrate suspensions via liquid antisolvent precipitation. Drug Dev Ind Pharm 2014;40:1693–703
   PubMed Web of Science ®Google Scholar
• Wei L, Ji Y, Gong W, et al. Preparation, physical characterization and pharmacokinetic study of paclitaxel nanocrystals. Drug Dev Ind Pharm 2014. [Epub ahead of print]. doi:10.3109/03639045.2014.950272
   Web of Science ®Google Scholar
• Lindenberg C, Schöll J, Vicum, L, et al. Experimental characterization and multi-scale modeling of mixing in static mixers. Chem Eng Sci 2008;63:4135–49
   Web of Science ®Google Scholar
• Lacerda SP. Improvement of dissolution rate of a new antiretroviral drug using an anti-solvent crystallization technology [octoral thesis]. Génie des procédés et de l'Environnement, 01-02-2013, INPT
   Google Scholar
• Asthana R, Sobczak N. Wettability, spreading, and interfacial phenomena in high-temperature coatings. J Met Electronic Ed [Online] 2000;52:1–19. Available from: http://www.tms.org/pubs/journals/JOM/0001/Asthana/Asthana-0001.html [last accessed 24 Jul 2014]
   Google Scholar
• Ali HSM, York P, Blagden N. Preparation of hydrocortisone nanosuspension through a bottom-up nanoprecipitation technique using microfluidic reactors. Int J Pharm 2009;375:107–13
   PubMed Web of Science ®Google Scholar
• Douroumis D, Fahr A. Nano- and micro-particulate formulations of poorly watersoluble drugs by using a novel optimized technique. Eur J Pharm Biopharm 2006;63:173–5
   PubMed Web of Science ®Google Scholar
• Thakur RK, Vial C, Nigam KDP, et al. Static mixers in the process industries – a review. Chem Eng Res Des 2003;81:787–826
   Web of Science ®Google Scholar
• Vippagunta SR, Wang Z, Hornung S, Krill SL. Factors affecting the formation of eutectic solid dispersions and their dissolution behavior. J Pharm Sci 2007;96:294–304
   PubMed Web of Science ®Google Scholar
• Wu L, Zhang J, Watanabe W. Physical and chemical stability of drug nanoparticles. Adv Drug Deliv Rev 2011;63:456–69
   PubMed Web of Science ®Google Scholar
• Thorat AA, Dalvi SV. Liquid antisolvent precipitation and stabilization of nanoparticles of poorly water soluble drugs in aqueous suspensions: recent developments and future perspective. Chem Eng J 2012;181–2:1–34
   Web of Science ®Google Scholar
• Pardeike J, Strohmeier DM, Schrödl N, et al. Nanosuspensions as advanced printing ink for accurate dosing of poorly soluble drugs in personalized medicines. Int J Pharm 2011;420:93–100
   PubMed Web of Science ®Google Scholar
• Shi J. Steric stabilization: literature review: steric stabilization. Ohio State University. Group Inorganic Materials- Literature Review [Online] 2002;1–43. Available from: http://muri.lci.kent.edu/References/NIM_Papers/stabilization_of_NP_suspensions/2002_Shi_steric_stabilization.pdf [last accessed 4 Aug 2014]
   Google Scholar
• Grahame DC. The electrical double layer and the theory of electrocapillarity. Chem Rev 1947;41:441–501
   PubMed Web of Science ®Google Scholar
• Laurier LS, Elaine NS, Marangoni DG. Surfactants and their applications. Annu Rep Prog Chem C 2003;99:3–48
   Google Scholar
• Claesson PM, Ninham BW. pH-dependent interactions between adsorbed chitosan layers. Langmuir 1992;8:1406–12
   Web of Science ®Google Scholar
• Zhang Z, Le Y, Wang J, et al. Irbesartan drug formulated as nanocomposite particles for the enhancement of the dissolution rate. Particuology 2012;10:462–67
   Web of Science ®Google Scholar
• Yue PF, Yuan HL, Yang M, et al. Preparation, characterization, and pharmacokinetic evaluation of puerarin submicron emulsion. PDA J Pharm Sci Technol 2008;62:32–45
   PubMedGoogle Scholar
• Patel VR, Agrawal YK. Nanosuspension: an approach to enhance solubility of drugs. J Adv Pharm Technol Res 2011;2:81–7
   PubMedGoogle Scholar
• Sun Y, Zhu L, Wu T, et al. Stability of amorphous pharmaceutical solids: crystal growth mechanisms and effect of polymer additives. AAPS J 2012;14:380–8
   PubMed Web of Science ®Google Scholar
• Silva R, Ferreira H, Carvalho AC, et al. Protein microspheres as suitable devices for piroxicam release. Colloid Surface B 2012;92:277–85
   PubMed Web of Science ®Google Scholar
• Viçosa A, Letourneau J-J, Espitalier F, Ré MI. An innovative antisolvent precipitation process as a promising technique to prepare ultrafine rifampicin particles. J Cryst Growth 2012;342:80–7
   Web of Science ®Google Scholar
• Bilati U, Allémann E, Doelker E. Development of a nanoprecipitation method intended for the entrapment of hydrophilic drugs into nanoparticles. Eur J Pharm Sci 2005;24:67–75
   PubMed Web of Science ®Google Scholar
• Kipp JE. The role of solid nanoparticle technology in the parenteral delivery of poorly water-soluble drugs. Int J Phar 2004;284:109–22
   PubMed Web of Science ®Google Scholar
• Cho E, Cho W, Cha KH, et al. Enhanced dissolution of megestrol acetate microcrystals prepared by antisolvent precipitation process using hydrophilic additives. Int J Pharm 2010;396:91–8
   PubMed Web of Science ®Google Scholar
• Salvalaglio M, Vetter T, Giberti F, et al. Uncovering molecular details of urea crystal growth in the presence of additives. J Am Chem Soc 2012;134:17221–33
   PubMed Web of Science ®Google Scholar
• Lechuga-Ballesteros D, Rodríguez-Hornedo N. The relation between adsorption of additives and crystal growth rate of L-alanine. J Colloid Interf Sci 1993;157:147–53
   Web of Science ®Google Scholar
• Takehara A, Fukuzaki S. Effect of the surface charge of stainless steel on adsorption behavior of pectin. Biocontrol Sci 2002;7:9–15
   Google Scholar