Comparison study of physicochemical and biopharmaceutics properties of hydrophobic drugs ground by two dry milling processes

References

• Al-Obaidi H, Lawrence MJ, Shah S, Moghul H, Al-Saden N, Bari F. 2013. Effect of drug–polymer interactions on the aqueous solubility of milled solid dispersions. Int J Pharm. 446(1–2):100–105.
   PubMedGoogle Scholar
• Amidon GL, Lennernäs H, Shah VP, Crison JR. 1995. A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm Res. 12(3):413–420.
   PubMed Web of Science ®Google Scholar
• Borba PAA, Pinotti M, de Campos CEM, Pezzini BR, Stulzer HK. 2016. Sodium alginate as a potential carrier in solid dispersion formulations to enhance dissolution rate and apparent water solubility of BCS II drugs. Carbohydr Polym. 137:350–359.
   PubMed Web of Science ®Google Scholar
• Branham ML, Moyo T, Govender T. 2012. Preparation and solid-state characterization of ball milled saquinavir mesylate for solubility enhancement. Eur J Pharm Biopharm. 80(1):194–202.
   PubMed Web of Science ®Google Scholar
• Chamarthy SP, Pinal R. 2008. The nature of crystal disorder in milled pharmaceutical materials. Colloids Surf A. 331(1–2):68–75.
   Google Scholar
• Chaudhari SP, Dugar RP. 2017. Application of surfactants in solid dispersion technology for improving solubility of poorly water soluble drugs. J Drug Delivery Sci Technol. 41:68–77.
   Web of Science ®Google Scholar
• Chaudhary A, Nagaich U, Gulati N, Sharma VK, Khosa RL. 2012. Enhancement of solubilization and bioavailability of poorly soluble drugs by physical and chemical modifications: a recent review. J Adv Pharm Educ Res. 2:32–67.
   Google Scholar
• Chikhalia V, Forbes RT, Storey RA, Ticehurst M. 2006. The effect of crystal morphology and mill type on milling induced crystal disorder. Eur J Pharm Sci. 27(1):19–26.
   PubMed Web of Science ®Google Scholar
• Columbano A, Buckton G, Wikeley P. 2003. Characterisation of surface modified salbutamol sulphate-alkylpolyglycoside microparticles prepared by spray drying. Int J Pharm. 253(1–2):61–70.
   PubMed Web of Science ®Google Scholar
• Da Silva FLO, Marques MBDF, Kato KC, Carneiro G. 2020. Nanonization techniques to overcome poor water-solubility with drugs. Expert Opin Drug Discov. 15(7):853–864.
   PubMed Web of Science ®Google Scholar
• De Gusseme A, Neves C, Willart JF, Rameau A, Descamps M. 2008. Ordering and disordering of molecular solids upon mechanical milling: the case of fananserine. J Pharm Sci. 97(11):5000–5012.
   PubMed Web of Science ®Google Scholar
• de Paiva Lacerda S, Espitalier F, Hoffart V, Ré MI. 2015. Liquid anti-solvent recrystallization to enhance dissolution of CRS 74, a new antiretroviral drug. Drug Dev Ind Pharm. 41(11):1910–1920.
   PubMed Web of Science ®Google Scholar
• Dedroog S, Huygens C, Van den Mooter G. 2019. Chemically identical but physically different: a comparison of spray drying, hot melt extrusion and cryo-milling for the formulation of high drug loaded amorphous solid dispersions of naproxen. Eur J Pharm Biopharm. 135:1–12.
   PubMed Web of Science ®Google Scholar
• Dujardin N, Willart JF, Dudognon E, Danède F, Descamps M. 2013. Mechanism of solid state amorphization of glucose upon milling. J Phys Chem B. 117(5):1437–1443.
   PubMed Web of Science ®Google Scholar
• Einfalt T, Planinšek O, Hrovat K. 2013. Methods of amorphization and investigation of the amorphous state. Acta Pharm. 63(3):305–334.
   PubMed Web of Science ®Google Scholar
• El-Badry M, Fetih G, Fathy M. 2009. Improvement of solubility and dissolution rate of indomethacin by solid dispersions in gelucire 50/13 and PEG4000. Saudi Pharm J. 17(3):217–225.
   PubMedGoogle Scholar
• Feng T, Pinal R, Carvajal MT. 2008. Process induced disorder in crystalline materials: differentiating defective crystals from the amorphous form of griseofulvin. J Pharm Sci. 97(8):3207–3221.
   PubMed Web of Science ®Google Scholar
• Fix I, Steffens K. 2004. Quantifying low amorphous or crystalline amounts of alpha-lactose-monohydrate using X-ray powder diffraction, near-infrared spectroscopy, and differential scanning calorimetry. Drug Dev Ind Pharm. 30(5):513–523.
   PubMed Web of Science ®Google Scholar
• Friedrich H, Nada A, Bodmeier R. 2005. Solid state and dissolution rate characterization of co-ground mixtures of nifedipine and hydrophilic carriers. Drug Dev Ind Pharm. 31(8):719–728.
   PubMed Web of Science ®Google Scholar
• Garg A, Singh S, Rao VU, Bindu K, Balasubramaniam J. 2009. Solid state interaction of raloxifene HCl with different hydrophilic carriers during co-grinding and its effect on dissolution rate. Drug Dev Ind Pharm. 35(4):455–470.
   PubMed Web of Science ®Google Scholar
• Gotor FJ, Achimovicova M, Real C, Balaz P. 2013. Influence of the milling parameters on the mechanical work intensity in planetary mills. Powder Technol. 233:1–7.
   Web of Science ®Google Scholar
• Guo Y, Shalaev E, Smith S. 2013. Physical stability of pharmaceutical formulations: solid-state characterization of amorphous dispersions. TrAC Trends Anal Chem. 49:137–144.
   Web of Science ®Google Scholar
• Hadjittofis E, Isbell MA, Karde V, Varghese S, Ghoroi C, Heng JYY. 2018. Influences of crystal anisotropy in pharmaceutical process development. Pharm Res. 35(5):100.
   PubMed Web of Science ®Google Scholar
• Hagbani TA, Nazzal S. 2017. Curcumin complexation with cyclodextrins by the autoclave process: method development and characterization of complex formation. Int J Pharm. 520(1–2):173–180.
   PubMedGoogle Scholar
• Han X, Ghoroi C, To D, Chen Y, Davé R. 2011. Simultaneous micronization and surface modification for improvement of flow and dissolution of drug particles. Int J Pharm. 415(1–2):185–195.
   PubMed Web of Science ®Google Scholar
• Humayun HY, Shaarani MNNM, Warrior A, Abdullah B, Salam MA. 2016. The effect of co-solvent on the solubility of a sparingly soluble crystal of benzoic acid. Proc Eng. 148:1320–1325.
   Google Scholar
• Hussain A, Smith G, Khan KA, Bukhari NI, Pedge NI, Ermolina I. 2018. Solubility and dissolution rate enhancement of ibuprofen by co-milling with polymeric excipients. Eur J Pharm Sci. 123:395–403.
   PubMed Web of Science ®Google Scholar
• Jermain SV, Brough C, Williams RO. 2018. Amorphous solid dispersions and nanocrystal technologies for poorly water-soluble drug delivery – an update. Int J Pharm. 535(1–2):379–392.
   PubMedGoogle Scholar
• Jójárt I, Sovány T, Pintye-Hódi K, Kása P. 2012. Study of the behaviour of magnesium stearate with different specific surface areas on the surface of particles during mixing. J Adhes Sci Technol. 26(24):2737–2744.
   Web of Science ®Google Scholar
• Junyaprasert VB, Morakul B. 2015. Nanocrystals for enhancement of oral bioavailability of poorly water-soluble drugs. Asian J Pharm Sci. 10(1):13–23.
   Web of Science ®Google Scholar
• Kacso I, Rus L, Pop M, Borodi G, Bratu I. 2012. Structural characterization of ambazone salt with niflumic acid. Spectroscopy. 27(1):49–58.
   Web of Science ®Google Scholar
• Kho HX, Bae S, Bae S, Kim B-W, Kim JS. 2014. Planetary ball mill process in aspect of milling energy. J Korean Powder Metall Inst. 21(2):155–164.
   Google Scholar
• Kumar D, Worku ZA, Gao Y, Kamaraju VK, Glennon B, Babu RP, Healy AM. 2018. Comparison of wet milling and dry milling routes for ibuprofen pharmaceutical crystals and their impact on pharmaceutical and biopharmaceutical properties. Powder Technol. 330:228–238.
   Web of Science ®Google Scholar
• Kumar R, Thakur AK, Chaudhari P, Banerjee N. 2022. Particle size reduction techniques of pharmaceutical compounds for the enhancement of their dissolution rate and bioavailability. J Pharm Innov. 17(2):333–352.
   Web of Science ®Google Scholar
• Li J, Yang Y, Zhao M, Xu H, Ma J, Wang S. 2017. Improved oral bioavailability of probucol by dry media-milling. Mater Sci Eng C Mater Biol Appl. 78:780–786.
   PubMed Web of Science ®Google Scholar
• Ling Z, Wang T, Makarem M, Santiago Cintrón M, Cheng HN, Kang X, Bacher M, Potthast A, Rosenau T, King H, et al. 2019. Effects of ball milling on the structure of cotton cellulose. Cellulose. 26(1):305–328.
   Web of Science ®Google Scholar
• Loftsson T, Brewster ME. 2010. Pharmaceutical applications of cyclodextrins: basic science and product development. J Pharm Pharmacol. 62(11):1607–1621.
   PubMed Web of Science ®Google Scholar
• Loh ZH, Samanta AK, Heng PWS. 2015. Overview of milling techniques for improving the solubility of poorly water-soluble drugs. Asian J Pharm Sci. 10(4):255–274.
   Web of Science ®Google Scholar
• Mallick S, Pattnaik S, Swain K, De PK, Saha A, Ghoshal G, Mondal A. 2008. Formation of physically stable amorphous phase of ibuprofen by solid state milling with kaolin. Eur J Pharm Biopharm. 68(2):346–351.
   PubMed Web of Science ®Google Scholar
• Mallick S, Pradhan SK, Mohapatra R. 2013. Effects of microcrystalline cellulose based comilled powder on the compression and dissolution of ibuprofen. Int J Biol Macromol. 60:148–155.
   PubMed Web of Science ®Google Scholar
• Mártha C, Kürti L, Farkas G, Jójárt-Laczkovich O, Szalontai B, Glässer E, Deli MA, Szabó-Révész P. 2013. Effects of polymers on the crystallinity of nanonized meloxicam during a co-grinding process. Eur Polym J. 49(9):2426–2432.
   Web of Science ®Google Scholar
• Mennini N, Maestrelli F, Cirri M, Mura P. 2016. Analysis of physicochemical properties of ternary systems of oxaprozin with randomly methylated-β-cyclodextrin and l-arginine aimed to improve the drug solubility. J Pharm Biomed Anal. 129:350–358.
   PubMed Web of Science ®Google Scholar
• Mir M, Hayat K, Hussain T, Waqas MK, Bukhari NI. 2018. Ball mill based on co-milling, a promising way to enhance solubility of poorly soluble drugs employing norfloxacin as model drug. Acta Pol Pharm. 75(1):155–168.
   Web of Science ®Google Scholar
• Newman A, Zografi G. 2014. Critical considerations for the qualitative and quantitative determination of process-induced disorder in crystalline solids. J Pharm Sci. 103(9):2595–2604.
   PubMed Web of Science ®Google Scholar
• Noyes AA, Whitney WR. 1897. The rate of solution of solid substances in their own solutions. J Am Chem Soc. 19(12):930–934.
   Google Scholar
• Nugrahani I, Jessica MA. 2021. Amino acids as the potential co-former for co-crystal development: a review. Molecules. 26(11):3279.
   PubMed Web of Science ®Google Scholar
• Patterson JE, James MB, Forster AH, Lancaster RW, Butler JM, Rades T. 2007. Preparation of glass solutions of three poorly water soluble drugs by spray drying, melt extrusion and ball milling. Int J Pharm. 336(1):22–34.
   PubMed Web of Science ®Google Scholar
• Perissutti B, Passerini N, Trastullo R, Keiser J, Zanolla D, Zingone G, Voinovich D, Albertini B. 2017. An explorative analysis of process and formulation variables affecting comilling in a vibrational mill: the case of praziquantel. Int J Pharm. 533(2):402–412.
   PubMed Web of Science ®Google Scholar
• Phillips EM. 1997. An approach to estimate the amorphous content of pharmaceutical powders using calorimetry with no calibration standards. Int J Pharm. 149(2):267–271.
   Google Scholar
• Qin L, Niu Y, Wang Y, Chen X. 2018. Combination of phospholipid complex and submicron emulsion techniques for improving oral bioavailability and therapeutic efficacy of water-insoluble drug. Mol Pharm. 15(3):1238–1247.
   PubMedGoogle Scholar
• Sakher E, Loudjani N, Benchiheub M, Bououdina M. 2018. Influence of milling time on structural and microstructural parameters of Ni50 Ti50 prepared by mechanical alloying using Rietveld analysis. J Nanomater. 2018:1–11.
   Web of Science ®Google Scholar
• Saleki-Gerhardt A, Ahlneck C, Zografi G. 1994. Assessment of disorder in crystalline solids. Int J Pharm. 101(3):237–247.
   Web of Science ®Google Scholar
• Saravanan D, Muthudoss P, Khullar P, Venis R. 2021. Micronization and agglomeration: understanding the impact of API particle properties on dissolution and permeability using solid state and biopharmaceutical "Toolbox". J Pharm Innov. 16(1):136–151.
   Web of Science ®Google Scholar
• Serajuddin ATM. 2007. Salt formation to improve drug solubility. Adv Drug Deliv Rev. 59(7):603–616.
   PubMed Web of Science ®Google Scholar
• Sheng JJ, Kasim NA, Chandrasekharan R, Amidon GL. 2006. Solubilization and dissolution of insoluble weak acid, ketoprofen: effects of pH combined with surfactant. Eur J Pharm Sci. 29(3–4):306–314.
   PubMed Web of Science ®Google Scholar
• Sud S, Kamath A. 2013. Methods of size reduction and factors affecting size reduction in pharmaceutics. Int Res J Pharm. 4(8):57–64.
   Google Scholar
• Szunyogh T, Ambrus R, Szabó-Révész P. 2012. Formation of niflumic acid particle size by solvent diffusion and solvent evaporation as precipitation methods. J Drug Delivery Sci Technol. 22(4):307–312.
   Web of Science ®Google Scholar
• Szunyogh T, Ambrus R, Szabó-Révész P. 2013. Nanonization of niflumic acid by co-grinding. Adv Nanopart. 2(4):329–335.
   Google Scholar
• Taniguchi C, Kawabata Y, Wada K, Yamada S, Onoue S. 2014. Microenvironmental pH-modification to improve dissolution behavior and oral absorption for drugs with pH-dependent solubility. Expert Opin Drug Deliv. 11(4):505–516.
   PubMed Web of Science ®Google Scholar
• Tawfeek HM, Chavan T, Kunda NK. 2020. Effect of spray drying on amorphization of indomethacin nicotinamide cocrystals; optimization, characterization, and stability study. AAPS PharmSciTech. 21:181.
   PubMed Web of Science ®Google Scholar
• Van Duong T, Lüdeker D, Van Bockstal P-J, De Beer T, Van Humbeeck J, Van den Mooter G. 2018. Polymorphism of indomethacin in semicrystalline dispersions: formation, transformation, and segregation. Mol Pharm. 15(3):1037–1051.
   PubMedGoogle Scholar
• Venkatesh S, Li J, Xu Y, Vishnuvajjala R, Anderson BD. 1996. Intrinsic solubility estimation and pH-solubility behavior of cosalane NSC 658586, an extremely hydrophobic diprotic acid. Pharm Res. 13(10):1453–1459.
   PubMed Web of Science ®Google Scholar
• Wadhwa J, Nair A, Kumria R. 2012. Emulsion forming drug delivery system for lipophilic drugs. Acta Pol Pharm. 69:179–191.
   PubMed Web of Science ®Google Scholar