Development of amorphous solid dispersions of cannabidiol: Influence of the carrier, the hot-melt extrusion parameters and the use of a crystallization inhibitor
Jennotte, Olivier ; Université de Liège - ULiège > Unités de recherche interfacultaires > Centre Interdisciplinaire de Recherche sur le Médicament (CIRM)
Koch, Nathan ; Université de Liège - ULiège > Unités de recherche interfacultaires > Centre Interdisciplinaire de Recherche sur le Médicament (CIRM)
Lechanteur, Anna ; Université de Liège - ULiège > Département de pharmacie
Evrard, Brigitte ; Université de Liège - ULiège > Unités de recherche interfacultaires > Centre Interdisciplinaire de Recherche sur le Médicament (CIRM)
Language :
English
Title :
Development of amorphous solid dispersions of cannabidiol: Influence of the carrier, the hot-melt extrusion parameters and the use of a crystallization inhibitor
Millar, S.A., Maguire, R.F., Yates, A.S., O'sullivan, S.E., Towards better delivery of cannabidiol (Cbd). Pharmaceuticals 13 (2020), 1–15, 10.3390/ph13090219.
Scuderi, C., De Filippis, D., Iuvone, T., Blasio, A., Steardo, A., Cannabidiol in medicine: a review of its therapeutic potential in CNS disorders. Phyther. Res. 23 (2008), 597–602, 10.1002/ptr.
Corroon, J., Phillips, J.A., A cross-sectional study of cannabidiol users. Cannabis. Cannabinoid. Res. 3 (2018), 152–161, 10.1089/can.2018.0006.
Borges, R.S., Batista, J., Viana, R.B., Baetas, A.C., Orestes, E., Andrade, M.A., Honório, K.M., Da Silva, A.B.F., Understanding the molecular aspects of tetrahydrocannabinol and cannabidiol as antioxidants. Molecules 18 (2013), 12663–12674, 10.3390/molecules181012663.
Costa, B., Colleoni, M., Conti, S., Parolaro, D., Franke, C., Trovato, A.E., Giagnoni, G., Oral anti-inflammatory activity of cannabidiol, a non-psychoactive constituent of cannabis, in acute carrageenan-induced inflammation in the rat paw. Naunyn-Schmiedeberg's Arch. Pharmacol. 369 (2004), 294–299, 10.1007/s00210-004-0871-3.
Blaskovich, M.A.T., Kavanagh, A.M., Elliott, A.G., Zhang, B., Ramu, S., Amado, M., Lowe, G.J., Hinton, A.O., Pham, D.M.T., Zuegg, J., Beare, N., Quach, D., Sharp, M.D., Pogliano, J., Rogers, A.P., Lyras, D., Tan, L., West, N.P., Crawford, D.W., Peterson, M.L., Callahan, M., Thurn, M., The antimicrobial potential of cannabidiol. Commun. Biol., 4, 2021, 10.1038/s42003-020-01530-y.
Almeida, V., Levin, R., Peres, F.F., Niigaki, S.T., Calzavara, M.B., Zuardi, A.W., Hallak, J.E., Crippa, J.A., Abílio, V.C., Cannabidiol exhibits anxiolytic but not antipsychotic property evaluated in the social interaction test. Prog. Neuro-Psychopharmacol. Biol. Psychiatry 41 (2013), 30–35, 10.1016/j.pnpbp.2012.10.024.
Millar, S.A., Stone, N.L., Yates, A.S., O'Sullivan, S.E., A systematic review on the pharmacokinetics of cannabidiol in humans. Front. Pharmacol., 9, 2018, 10.3389/fphar.2018.01365.
Giacoppo, S., Bramanti, P., Mazzon, E., Sativex in the management of multiple sclerosis-related spasticity: an overview of the last decade of clinical evaluation. Mult. Scler. Relat. Disord. 17 (2017), 22–31, 10.1016/j.msard.2017.06.015.
Amidon, G.L., Lennernäs, 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. An Off. J. Am. Assoc. Pharm. Sci. 12 (1995), 413–420, 10.1023/A:1016212804288.
Kalepu, S., Nekkanti, V., Insoluble drug delivery strategies: review of recent advances and business prospects. Acta Pharm. Sin. B. 5 (2015), 442–453, 10.1016/j.apsb.2015.07.003.
Koch, N., Jennotte, O., Gasparrini, Y., Vandenbroucke, F., Lechanteur, A., Evrard, B., Cannabidiol aqueous solubility enhancement: comparison of three amorphous formulations strategies using different type of polymers. Int. J. Pharm., 589, 2020, 119812, 10.1016/j.ijpharm.2020.119812.
Perucca, E., Bialer, M., Critical aspects affecting cannabidiol oral bioavailability and metabolic elimination, and related clinical implications. CNS Drugs 34 (2020), 795–800, 10.1007/s40263-020-00741-5.
Hecq, J., Deleers, M., Fanara, D., Vranckx, H., Amighi, K., Preparation and characterization of nanocrystals for solubility and dissolution rate enhancement of nifedipine. Int. J. Pharm. 299 (2005), 167–177, 10.1016/j.ijpharm.2005.05.014.
Rawat, S., Jain, S.K., Solubility enhancement of celecoxib using β-cyclodextrin inclusion complexes. Eur. J. Pharm. Biopharm. 57 (2004), 263–267, 10.1016/j.ejpb.2003.10.020.
Serajuddin, A.T.M., Salt formation to improve drug solubility. Adv. Drug Deliv. Rev. 59 (2007), 603–616, 10.1016/j.addr.2007.05.010.
Pan, X., Julian, T., Augsburger, L., Increasing the dissolution rate of a low-solubility drug through a crystalline-amorphous transition: a case study with indomethicin. Drug Dev. Ind. Pharm. 34 (2008), 221–231, 10.1080/03639040701580606.
Hancock, B.C., Disordered drug delivery: destiny, dynamics and the Deborah number. Pharm. J., 267, 2001, 520, 10.1211/0022357021778989.
Novakovic, D., Isomäki, A., Pleunis, B., Fraser-Miller, S.J., Peltonen, L., Laaksonen, T., Strachan, C.J., Understanding dissolution and crystallization with imaging: a surface point of view. Mol. Pharm. 15 (2018), 5361–5373, 10.1021/acs.molpharmaceut.8b00840.
Skrdla, P.J., Floyd, P.D., Dell'Orco, P.C., Predicting the solubility enhancement of amorphous drugs and related phenomena using basic thermodynamic principles and semi-empirical kinetic models. Int. J. Pharm., 567, 2019, 118465, 10.1016/j.ijpharm.2019.118465.
Alonzo, D.E., Zhang, G.G.Z., Zhou, D., Gao, Y., Taylor, L.S., Understanding the behavior of amorphous pharmaceutical systems during dissolution. Pharm. Res. (N. Y.) 27 (2010), 608–618, 10.1007/s11095-009-0021-1.
Mistry, P., Amponsah-efah, K.K., Suryanarayanan, R., Rapid assessment of the physical stability of amorphous solid dispersions. Cryst. Growth Des. 17 (2017), 2478–2485, 10.1021/acs.cgd.6b01901.
Raina, S.A., Eerdenbrugh, B.V.A.N., Alonzo, D.E., Mo, H., Zhang, G.G.Z., Gao, Y.I., Taylor, L.S., Trends in the precipitation and crystallization behavior of supersaturated aqueous solutions of poorly water-soluble drugs assessed using synchrotron radiation. Pharm. Drug Deliv. Pharm. Technol. Trends., 104, 2015, 1981, 10.1002/jps.24423 1992.
Van Den Mooter, G., The use of amorphous solid dispersions: a formulation strategy to overcome poor solubility and dissolution rate. Drug Discov. Today Technol. 9 (2012), e79–e85, 10.1016/j.ddtec.2011.10.002.
Thiry, J., Kok, M.G.M., Collard, L., Frère, A., Krier, F., Fillet, M., Evrard, B., Bioavailability enhancement of itraconazole-based solid dispersions produced by hot melt extrusion in the framework of the Three Rs rule. Eur. J. Pharmaceut. Sci. 99 (2017), 1–8, 10.1016/j.ejps.2016.12.001.
Sun, D.D., Ju, T.C.R., Lee, P.I., Enhanced kinetic solubility profiles of indomethacin amorphous solid dispersions in poly(2-hydroxyethyl methacrylate) hydrogels. Eur. J. Pharm. Biopharm. 81 (2012), 149–158, 10.1016/j.ejpb.2011.12.016.
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. 70 (2008), 493–499, 10.1016/j.ejpb.2008.05.023.
Ambike, A.A., Mahadik, K.R., Paradkar, A., Spray-dried amorphous solid dispersions of simvastatin, a low T g drug: in vitro and in vivo evaluations. Pharm. Res. (N. Y.) 22 (2005), 990–998, 10.1007/s11095-005-4594-z.
Chavan, R.B., Thipparaboina, R., Kumar, D., Shastri, N.R., Evaluation of the inhibitory potential of HPMC, PVP and HPC polymers on nucleation and crystal growth. RSC Adv. 6 (2016), 77569–77576, 10.1039/c6ra19746a.
Tajarobi, F., Larsson, A., Matic, H., Abrahmsén-Alami, S., The influence of crystallization inhibition of HPMC and HPMCAS on model substance dissolution and release in swellable matrix tablets. Eur. J. Pharm. Biopharm. 78 (2011), 125–133, 10.1016/j.ejpb.2010.11.020.
Abu-Diak, O.A., Jones, D.S., Andrews, G.P., An investigation into the dissolution properties of celecoxib melt extrudates: understanding the role of polymer type and concentration in stabilizing supersaturated drug concentrations. Mol. Pharm. 8 (2011), 1362–1371, 10.1021/mp200157b.
Konno, H., Taylor, L.S., Ability of different polymers to inhibit the crystallization of amorphous felodipine in the presence of moisture. Pharm. Res. (N. Y.) 25 (2008), 969–978, 10.1007/s11095-007-9331-3.
Ueda, K., Higashi, K., Yamamoto, K., Moribe, K., The effect of HPMCAS functional groups on drug crystallization from the supersaturated state and dissolution improvement. Int. J. Pharm. 464 (2014), 205–213, 10.1016/j.ijpharm.2014.01.005.
B, S., Nollenberger, K., Gryczke, A., Meier, C.H., Dressman, J., Shmidt, M.U., Pair distribution function X-ray analysis explains dissolution characteristics of felodipine melt extrusion products. J. Pharm. Sci. 98 (2008), 1476–1486, 10.1002/jps.
Sarabu, S., Kallakunta, V.R., Bandari, S., Batra, A., Bi, V., Durig, T., Zhang, F., Repka, M.A., Hypromellose acetate succinate based amorphous solid dispersions via hot melt extrusion: effect of drug physicochemical properties. Carbohydr. Polym., 233, 2020, 115828, 10.1016/j.carbpol.2020.115828.
Singh, A., Van Den Mooter, G., Spray drying formulation of amorphous solid dispersions. Adv. Drug Deliv. Rev. 100 (2016), 27–50, 10.1016/j.addr.2015.12.010.
Potter, C., Tian, Y., Walker, G., Mccoy, C., Hornsby, P., Donnelly, C., Jones, D.S., Andrews, G.P., Novel supercritical carbon dioxide impregnation technique for the production of amorphous solid drug dispersions: a comparison to hot melt extrusion. https://doi.org/10.1021/mp500644h, 2015.
Dinunzio, J.C., Brough, C., Miller, D.A., Williams, R.O., Mcginity, J.W., European Journal of Pharmaceutical Sciences Applications of KinetiSol ® Dispersing for the production of plasticizer free amorphous solid dispersions. Eur. J. Pharmaceut. Sci. 40 (2010), 179–187, 10.1016/j.ejps.2010.03.002.
Thiry, J., Krier, F., Ratwatte, S., Thomassin, J., Jerome, C., Evrard, B., Hot-melt extrusion as a continuous manufacturing process to form ternary cyclodextrin inclusion complexes. Eur. J. Pharmaceut. Sci. 96 (2017), 590–597, 10.1016/j.ejps.2016.09.032.
Thiry, J., Krier, F., Evrard, B., A review of pharmaceutical extrusion: critical process parameters and. Int. J. Pharm. 479 (2015), 227–240, 10.1016/j.ijpharm.2014.12.036.
Vynckier, A.K., Dierickx, L., Voorspoels, J., Gonnissen, Y., Remon, J.P., Vervaet, C., Hot-melt co-extrusion: requirements, challenges and opportunities for pharmaceutical applications. J. Pharm. Pharmacol. 66 (2014), 167–179, 10.1111/jphp.12091.
Agrawal, A.M., Dudhedia, M.S., Zimny, E., Hot melt extrusion: development of an amorphous solid dispersion for an insoluble drug from mini-scale to clinical scale. AAPS PharmSciTech 17 (2016), 133–147, 10.1208/s12249-015-0425-7.
Thiry, J., Lebrun, P., Vinassa, C., Adam, M., Netchacovitch, L., Ziemons, E., Hubert, P., Krier, F., Evrard, B., Continuous production of itraconazole-based solid dispersions by hot melt extrusion: preformulation, optimization and design space determination. Int. J. Pharm. 515 (2016), 114–124, 10.1016/j.ijpharm.2016.10.003.
Tian, Y., Jacobs, E., Jones, D.S., McCoy, C.P., Wu, H., Andrews, G.P., The design and development of high drug loading amorphous solid dispersion for hot-melt extrusion platform. Int. J. Pharm., 586, 2020, 119545, 10.1016/j.ijpharm.2020.119545.
Shibata, Y., Fujii, M., Sugamura, Y., Yoshikawa, R., Fujimoto, S., Nakanishi, S., Motosugi, Y., Koizumi, N., Yamada, M., Ouchi, K., Watanabe, Y., The preparation of a solid dispersion powder of indomethacin with crospovidone using a twin-screw extruder or kneader. Int. J. Pharm. 365 (2009), 53–60, 10.1016/j.ijpharm.2008.08.023.
Liu, H., Wang, P., Zhang, X., Shen, F., Gogos, C.G., Effects of extrusion process parameters on the dissolution behavior of indomethacin in Eudragit. E PO. Solid. dispersions. 383 (2010), 161–169, 10.1016/j.ijpharm.2009.09.003.
Pawar, J., Suryawanshi, D., Moravkar, K., Aware, R., Shetty, V., Maniruzzaman, M., Amin, P., Study the influence of formulation process parameters on solubility and dissolution enhancement of efavirenz solid solutions prepared by hot-melt extrusion: a QbD methodology. Drug Deliv. Transl. Res. 8 (2018), 1644–1657, 10.1007/s13346-018-0481-0.
Qian, F., Huang, J., Hussain, M.A., Drug-polymer solubility and miscibility: stability consideration and practical challenges in amorphous solid dispersion development. J. Pharm. Sci. 99 (2010), 2941–2947, 10.1002/jps.22074.
Pestieau, A., Krier, F., Brouwers, A., Streel, B., Evrard, B., Selection of a Discriminant and Biorelevant in Vitro Dissolution Test for the Development of Fenofibrate Self-Emulsifying Lipid-Based Formulations. 2016, Elsevier B.V., 10.1016/j.ejps.2016.04.038.
Versantvoort, C.H.M., Oomen, A.G., Van De Kamp, E., Rompelberg, C.J.M., Sips, A.J.A.M., Applicability of an in vitro digestion model in assessing the bioaccessibility of mycotoxins from food. Food Chem. Toxicol. 43 (2005), 31–40, 10.1016/j.fct.2004.08.007.
Mistry, P., Mohapatra, S., Gopinath, T., Vogt, F.G., Suryanarayanan, R., Role of the strength of drug-polymer interactions on the molecular mobility and crystallization inhibition in ketoconazole solid dispersions. Mol. Pharm. 12 (2015), 3339–3350, 10.1021/acs.molpharmaceut.5b00333.
Tres, F., Treacher, K., Booth, J., Hughes, L.P., Wren, S.A.C., Aylott, J.W., Burley, J.C., Indomethacin-kollidon VA64 extrudates: a mechanistic study of pH-dependent controlled release. https://doi.org/10.1021/acs.molpharmaceut.5b00979, 2016.
Wei, C., Solanki, N.G., Vasoya, J.M., Shah, A.V., Serajuddin, A.T.M., Development of 3D printed tablets by fused deposition modeling using polyvinyl alcohol as polymeric matrix for rapid drug release. J. Pharm. Sci. 109 (2020), 1558–1572, 10.1016/j.xphs.2020.01.015.
Leuner, C., Dressman, J., Improving drug solubility for oral delivery using solid dispersions. Eur. J. Pharm. Biopharm. 50 (2000), 47–60, 10.1016/S0939-6411(00)00076-X.
Bavishi, D.D., Borkhataria, C.H., Spring and parachute: how cocrystals enhance solubility. Prog. Cryst. Growth Char. Mater. 62 (2016), 1–8, 10.1016/j.pcrysgrow.2016.07.001.
Li, J., Lee, I.W., Shin, G.H., Chen, X., Park, H.J., Curcumin-Eudragit® E PO solid dispersion: a simple and potent method to solve the problems of curcumin. Eur. J. Pharm. Biopharm. 94 (2015), 322–332, 10.1016/j.ejpb.2015.06.002.