Polymeric Precipitation Inhibitor As an Effective Trigger to Convert Supersaturated Into Supersaturable State In Vivo

References

• Brouwers J , BrewsterME , AugustijnsP. Supersaturating drug delivery systems: the answer to solubility-limited oral bioavailability. J. Pharm. Sci.98, 2549–2572 (2009).
   PubMed Web of Science ®Google Scholar
• Patel DD , AndersonBD. Effect of precipitation inhibitors on indomethacin supersaturation maintenance: mechanisms and modeling. Mol. Pharm.11, 1489–1499 (2014).
   PubMedGoogle Scholar
• Fong SYK , Bauer-BrandlA , BrandlM. Oral bioavailability enhancement through supersaturation: an update and meta-analysis. Expert Opin. Drug Deliv.14, 403–426 (2017).
   PubMed Web of Science ®Google Scholar
• Kawakami K . Theory and practice of supersaturatable formulations for poorly soluble drugs. Ther. Deliv.6, 339–352 (2015).
   PubMed Web of Science ®Google Scholar
• Patel DD , AndersonBD. Adsorption of polyvinylpyrrolidone and its impact on maintenance of aqueous supersaturation of indomethacin via crystal growth inhibition. J. Pharm. Sci.104, 2923–2933 (2015).
   PubMed Web of Science ®Google Scholar
• Yang M , GongW , WangY , ShanL , LiY , GaoC. Bioavailability improvement strategies for poorly water-soluble drugs based on the supersaturation mechanism: an update. J. Pharm. Pharm. Sci.19, 208 (2016).
   PubMed Web of Science ®Google Scholar
• Dahan A , BeigA , LindleyD , MillerJH. The solubility permeability interplay and oral formulation degisn: two heads are better than one. Adv. Drug Deliv. Rev.101, 99–107 (2016).
   PubMed Web of Science ®Google Scholar
• Kleppe MS , Forney-StevensKM , HaskellRJ , BognerRH. Mathematical models to explore potential effects of supersaturation and precipitation on oral bioavailability of poorly soluble drugs. AAPS J.17, 902–917 (2015).
   PubMed Web of Science ®Google Scholar
• Price DJ , DitzingerF , KoehlNJet al. Approaches to increase mechanistic understanding and aid in the selection of precipitation inhibitors for supersaturating formulations - a pearrl review. J. Pharm. Pharmacol.71(4), 483–509 (2018).
   PubMed Web of Science ®Google Scholar
• Han YR , LeePI. Effect of extent of supersaturation on the evolution of kinetic solubility profiles. Mol. Pharm.14, 206–220 (2017).
   PubMed Web of Science ®Google Scholar
• Augustijns P , BrewsterME. Supersaturating drug delivery systems: fast is not necessarily good enough. J. Pharm. Sci.101, 7–9 (2012).
   PubMed Web of Science ®Google Scholar
• Patel DD , AndersonBD. Maintenance of supersaturation ii: indomethacin crystal growth kinetics versus degree of supersaturation. J. Pharm. Sci.102, 1544–1553 (2013).
   PubMed Web of Science ®Google Scholar
• Lindfors L , ForssénS , WestergrenJ , OlssonU. Nucleation and crystal growth in supersaturated solutions of a model drug. J. Colloid Interface Sci.325, 404–413 (2008).
   PubMed Web of Science ®Google Scholar
• Otsuka N , UedaK , OhyagiNet al. An Insight into different stabilization mechanisms of phenytoin derivatives supersaturation by HPMC and PVP. J. Pharm. Sci.104, 2574–2582 (2015).
   PubMed Web of Science ®Google Scholar
• Ozaki S , KushidaI , YamashitaT , HasebeT , ShiraiO , KanoK. Inhibition of crystal nucleation and growth by water-soluble polymers and its impact on the supersaturation profiles of amorphous drugs. J. Pharm. Sci.102, 2273–2281 (2013).
   PubMed Web of Science ®Google Scholar
• Fornells E , FuguetE , MañéMet al. Effect of vinylpyrrolidone polymers on the solubility and supersaturation of drugs; a study using the cheqsol method. Eur. J. Pharm. Sci.117, 227–235 (2018).
   PubMed Web of Science ®Google Scholar
• Alhayali A , SeloMA , EhrhardtC , VelagaS. Investigation of supersaturation and in vitro permeation of the poorly water soluble drug ezetimibe. Eur. J. Pharm. Sci.117, 147–153 (2018).
   PubMed Web of Science ®Google Scholar
• Jackson MJ , KesturUS , HussainMA , TaylorLS. Characterization of supersaturated danazol solutions – impact of polymers on solution properties and phase transitions. Pharm. Res.33, 1276–1288 (2016).
   PubMed Web of Science ®Google Scholar
• Terebetski JL , Michniak-KohnB. Combining ibuprofen sodium with cellulosic polymers: a deep dive into mechanisms of prolonged supersaturation. Int. J. Pharm.475, 536–546 (2014).
   PubMed Web of Science ®Google Scholar
• Xu S , DaiWG. Drug precipitation inhibitors in supersaturable formulations. Int. J. Pharm.453, 36–43 (2013).
   PubMed Web of Science ®Google Scholar
• Raghavan S , TrividicA , DavisA , HadgraftJ. Crystallization of hydrocortisone acetate: influence of polymers. Int. J. Pharm.212, 213–221 (2001).
   PubMed Web of Science ®Google Scholar
• Xie S , PoornacharySK , ChowPS , TanRB. H. Direct precipitation of micron-size salbutamol sulfate: new insights into the action of surfactants and polymeric additives. Cryst. Growth Des.10, 3363–3371 (2010).
   Web of Science ®Google Scholar
• Trasi NS , TaylorLS. Effect of polymers on nucleation and crystal growth of amorphous acetaminophen. Cryst. Eng. Comm.14, 5188 (2012).
   Google Scholar
• Gao P , AkramiA , AlvarezFet al. Characterization and optimization of AMG 517 supersaturatable self-emulsifying drug delivery system (S-SEDDS) for improved oral absorption. J. Pharm. Sci.98, 516–528 (2009).
   PubMed Web of Science ®Google Scholar
• Ilevbare GA , LiuH , EdgarKJ , TaylorLS. 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 (2012).
   Web of Science ®Google Scholar
• Garekani HA , FordJL , RubinsteinMH , Rajabi-SiahboomiAR. Highly compressible paracetamol: I: crystallization and characterization. Int. J. Pharm.208, 87–99 (2000).
   PubMed Web of Science ®Google Scholar
• Kestur US , LeeH , SantiagoD , RinaldiC , WonYY , TaylorLS. 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 (2010).
   Web of Science ®Google Scholar
• Miller DA , DiNunzioJC , YangW , McGinityJW , WilliamsRO. Enhanced in-vivo absorption of itraconazole via stabilization of supersaturation following acidic-to-neutral pH transition. Drug Dev. Ind. Pharm.34(8), 890–902 (2008).
   PubMed Web of Science ®Google Scholar
• Jaisamut P , WiwattanawongsaK , GraidistP , SangsenY , WiwattanapatapeeR. Enhanced oral bioavailability of curcumin using a supersaturatable self-microemulsifying system incorporating a hydrophilic polymer; in vitro and in vivo investigations. AAPS Pharm. Sci. Tech.19, 730–740 (2018).
   PubMed Web of Science ®Google Scholar
• DiNunzio JC , MillerDA , YangW , McGinityJW , WilliamsRO. Amorphous compositions using concentration enhancing polymers for improved bioavailability of itraconazole. Mol. Pharm.5, 968–980 (2008).
   PubMed Web of Science ®Google Scholar
• Usui F , MaedaK , KusaiA , NishimuraK , YamamotoK. Inhibitory effects of water-soluble polymers on precipitation of RS-8359. Int. J. Pharm.154, 59–66 (1997).
   Web of Science ®Google Scholar
• Chavan RB , ThipparaboinaR , KumarD , ShastriNR. Evaluation of the inhibitory potential of HPMC, PVP and HPC polymers on nucleation and crystal growth. RSC Adv.6, 77569–77576 (2016).
   Web of Science ®Google Scholar
• Dai WG . In vitro methods to assess drug precipitation. Int. J. Pharm.393, 1–16 (2010).
   PubMed Web of Science ®Google Scholar
• Bevernage J , ForierT , BrouwersJ , TackJ , AnnaertP , AugustijnsP. Excipient-mediated supersaturation stabilization in human intestinal fluids. Mol. Pharm.8, 564–570 (2011).
   PubMed Web of Science ®Google Scholar
• Bevernage J , HensB , BrouwersJ , TackJ , AnnaertP , AugustijnsP. Supersaturation in human gastric fluids. Eur. J. Pharm. Biopharm.81, 184–189 (2012).
   PubMed Web of Science ®Google Scholar
• Bi M , KyadA , KiangYH , Alvarez-NunezF , AlvarezF. Enhancing and sustaining AMG 009 dissolution from a matrix tablet via microenvironmental pH modulation and supersaturation. AAPS PharmSciTech12, 1157–1162 (2011).
   PubMed Web of Science ®Google Scholar
• Sun DD , LeePI. Haste makes waste: the interplay between dissolution and precipitation of supersaturating formulations. AAPS J.17, 1317–1326 (2015).
   PubMed Web of Science ®Google Scholar
• Zhang S , SunM , ZhaoYet al. Molecular mechanism of polymer-assisting supersaturation of poorly water-soluble loratadine based on experimental observations and molecular dynamic simulations. Drug. Deliv. Transl. Res.7, 738–749 (2017).
   PubMed Web of Science ®Google Scholar
• Ueda K , HigashiK , YamamotoK , MoribeK. In situ molecular elucidation of drug supersaturation achieved by nano-sizing and amorphization of poorly water-soluble drug. Eur. J. Pharm. Sci.77, 79–89 (2015).
   PubMed Web of Science ®Google Scholar
• Gao P , RushBD , PfundWPet al. Development of a supersaturable SEDDS (S-SEDDS) formulation of paclitaxel with improved oral bioavailability. J. Pharm. Sci.92, 2386–2398 (2003).
   PubMed Web of Science ®Google Scholar
• Bevernage J , BrouwersJ , BrewsterME , AugustijnsP. Evaluation of gastrointestinal drug supersaturation and precipitation: strategies and issues. Int. J. Pharm.453, 25–35 (2013).
   PubMed Web of Science ®Google Scholar
• Sun DD , LeePI. Evolution of supersaturation of amorphous pharmaceuticals: nonlinear rate of supersaturation generation regulated by matrix diffusion. Mol. Pharm.12, 1203–1215 (2015).
   PubMed Web of Science ®Google Scholar
• Patel DD , AndersonBD. Maintenance of supersaturation ii: indomethacin crystal growth kinetics versus degree of supersaturation. J. Pharm. Sci.102(5), 1544–1553 (2013).
   PubMed Web of Science ®Google Scholar
• Kostewicz ES , WunderlichM , BraunsU , BeckerR , BockT , DressmanJB. Predicting the precipitation of poorly soluble weak bases upon entry in the small intestine. J. Pharm. Pharmacol.56, 43–51 (2004).
   PubMed Web of Science ®Google Scholar
• Gao P , ShiY. Characterization of supersaturatable formulations for improved absorption of poorly soluble drugs. AAPS J.14, 703–713 (2012).
   PubMed Web of Science ®Google Scholar
• Shin DJ , ChaeBR , GooYTet al. Improved dissolution and oral bioavailability of valsartan using a solidified supersaturable self-microemulsifying drug delivery system containing Gelucire 44/14. Pharmaceutics11, 1–19 (2019).
   Web of Science ®Google Scholar
• Suys EJA , ChalmersDK , PoutonCW , PorterCJH. Polymeric precipitation inhibitors promote fenofibrate supersaturation and enhance drug absorption from a type iv lipid-based formulation. Mol. Pharm.15, 2355–2371 (2018).
   PubMed Web of Science ®Google Scholar
• Jain A , KaurR , BegS , KushwahV , JainS , SinghB. Novel cationic nanomicellar supersaturable systems of raloxifene hyrochloride with enhanced biopharmaceutical attributes. Drug Dev. Trans. Res.8, 670–692 (2018).
   PubMed Web of Science ®Google Scholar
• Xie T , GaoW , TaylorLS. Impact of eudragit epo and hydroxypropyl methylcellulose on drug release rate, supersaturation, precipitation outcome and redissolution rate of indomethacin amorphous solid dispersions. Int. J. Pharm.531, 313–323 (2017).
   PubMed Web of Science ®Google Scholar
• Madsen CM , BoydB , RadesT , MullertzA. Supersaturation of Zafirlukast in fasted and fed intestinal media with and without precipitation inhibitors. Eur. J. Pharm.91, 31–39 (2016).
   Google Scholar
• Wang C , TongQ , HouX , HuS , FangJ , SunCC. Enhancing bioavailability of dihydromyricetin through inhibiting precipitation of soluble cocrystals by a crystallization inhibitor. Cryst. Growth Des.16, 5030–5039 (2016).
   Web of Science ®Google Scholar
• Vora C , PatadiaR , MittalK , MashruR. Preparation and characterization of dipyridamole solid dispersions for stabilization of supersaturation: effect of precipitation inhibitors type and molecular weight. Pharm. Dev. Technol.21, 847–855 (2016).
   PubMed Web of Science ®Google Scholar
• Lee DH , YeomDW , SongYSet al. Improved oral absorption of dutasteride via Soluplus®-based supersaturable self-emulsifying drug delivery system (S-SEDDS). Int. J. Pharm.478, 341–347 (2015).
   PubMed Web of Science ®Google Scholar
• Yang X , ShenB , HuangY. Mechanistic study of HPMC-prolonged supersaturation of hydrocortisone. Cryst. Growth Des.15, 546–551 (2015).
   Web of Science ®Google Scholar
• Bandyopadhyay S , KatareOP , SinghB. Development of optimized supersaturable self-nanoemulsifying systems of ezetimibe: effect of polymers and efflux transporters. Expert. Opin. Drug. Deliv.11(4), 479–492 (2014).
   PubMed Web of Science ®Google Scholar
• Chauhan H , Hui-GuC , AtefE. Correlating the behavior of polymers in solution as precipitation inhibitor to its amorphous stabilization ability in solid dispersions. J. Pharm. Sci.102, 1924–1935 (2013).
   PubMed Web of Science ®Google Scholar
• Song WH , ParkJH , YeomDWet al. Enhanced dissolution of celecoxib by supersaturating self-emulsifying drug delivery system (S-SEDDS) Formulation. Arch. Pharm. Res.36, 69–78 (2013).
   PubMed Web of Science ®Google Scholar
• Dahan A , MillerJM. The solubility-permeability interplay and its implications in formulation design and development for poorly soluble drugs. AAPS J.14(2), 244–251 (2012).
   PubMed Web of Science ®Google Scholar
• Miller JM , BeigA , KriegBJet al. The solubility-permeability interplay: mechanistic modeling and predictive application of the impact of micellar solubilization on intestinal permeation. Mol. Pharm.8(5), 1848–1856 (2011).
   PubMedGoogle Scholar
• Guzman HR , TawaM , ZhangZet al. Combined use of crystalline salt forms and precipitation inhibitors to improve oral absorption of celecoxib from solid oral formulations. J. Pharm. Sci.96(10), 2686–2702 (2007).
   PubMed Web of Science ®Google Scholar
• Overhoff KA , McConvilleJT , YangW , JohnstonKP , PetersJI , WilliamsRO. Effect of stabilizer on the maximum degree and extent of supersaturation and oral absorption of tacrolimus made by ultra-rapid freezing. Pharm. Res.25(1), 167–175 (2008).
   PubMed Web of Science ®Google Scholar
• Miao L , LiangY , PanWet al. Effect of supersaturation on the oral bioavailability of paclitaxel/polymer amorphous solid dispersion. Drug. Deliv. Transl. Res.9(1), 344–356 (2019).
   PubMed Web of Science ®Google Scholar
• Bai A , WuC , LiuXet al. Development of a tin oxide carrier with mesoporous structure for improving the dissolution rate and oral relative bioavailability of fenofibrate. Drug. Des. Devel. Ther.12, 2129–2138 (2018).
   PubMed Web of Science ®Google Scholar
• Guivarc’h PH , VachonMG , FordyceDA. New fenofibrate formulation: results of six single-dose, clinical studies of bioavailability under fed and fasting conditions. Clin. Ther.26(9), 1456–1469 (2004).
   PubMed Web of Science ®Google Scholar
• Do TT , SpeybroeckM , MolsRet al. The conflict between in vitro release studies in human biorelevant media and the in-vivo exposure in rats of the lipophilic compound fenofibrate. Int. J. Pharm.414, 118–124 (2011).
   PubMed Web of Science ®Google Scholar