Discovery solubility measurement and assessment of small molecules with drug development in mind

Drug Discovery Today - Tập 27 - Trang 1315-1325 - 2022
Jaclyn A. Barrett1, Wenzhan Yang2, Suzanne M. Skolnik3, Lisa M. Belliveau4, Kellyn M. Patros4
1Synthetic Molecule Design and Development, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, IN 46221, USA
2Advanced Drug Delivery, Pharmaceutical Sciences, R&D, AstraZeneca, Boston, MA, USA
3Global Discovery Chemistry, Novartis Institutes for Biomedical Research, Cambridge, MA 02139, USA
4Drug Product Design, Pharmaceutical Sciences, Pfizer Inc., Groton, CT, USA

Tài liệu tham khảo

Sinha, 2018, Drug discovery and development: an overview, 19 Berdigaliyev, 2020, An overview of drug discovery and development, Future Med Chem., 12, 939, 10.4155/fmc-2019-0307 Sweetana, 1996, Solubility principles and practices for parenteral drug dosage form development, PDA J Pharm Sci Technol., 50, 330 Di, 2012, Bridging solubility between drug discovery and development, Drug Discov Today., 17, 486, 10.1016/j.drudis.2011.11.007 Manssour- Manssour-Triedo, 2016, Molecular and physicochemical factors governing solubility of the HIV gp41 ectodomain, Biophys J., 111, 700, 10.1016/j.bpj.2016.07.022 Bhattachar, 2017, Developability assessment of clinical candidates, 231 Landis, 2018, Commentary: why pharmaceutical scientists in early drug discovery are critical for influencing the design and selection of optimal drug candidates, AAPS PharmSciTech., 19, 1, 10.1208/s12249-017-0849-3 Evers, 2019, Peptide optimization at the drug discovery-development interface: tailoring of physicochemical properties toward specific formulation requirements, J Pharm Sci., 108, 1404, 10.1016/j.xphs.2018.11.043 Yang, 2020, The evolving druggability and developability space: chemically modified new modalities and emerging small molecules, AAPS Journal., 22, 21, 10.1208/s12248-019-0402-2 Gigante, 2021, Global testing of a consensus solubility assessment to enhance robustness of the WHO biopharmaceutical classification system, ADMET DMPK., 9, 23 Avdeef, 2016, Equilibrium solubility measurement of ionizable drugs - consensus recommendations for improving data quality, ADMET DMPK., 4, 117, 10.5599/admet.4.2.292 Yalkowsky, 1999 Sou, 2018, Automated assays for thermodynamic (equilibrium) solubility determination, Drug Discov Today: Tech., 27, 11, 10.1016/j.ddtec.2018.04.004 Vertzoni, 2022, UNGAP best practice for improving solubility data quality of orally administered drugs, Eur J Pharm Sci., 168, 10.1016/j.ejps.2021.106043 Ono, 2019, Harmonizing solubility measurement to lower inter-laboratory variance - progress of consortium of biopharmaceutical tools (CoBiTo) in Japan, ADMET DMPK., 7, 183, 10.5599/admet.704 Mathias, 2013, Assessing the risk of pH-dependent absorption for new molecular entities: a novel in vitro dissolution test, physicochemical analysis, and risk assessment strategy, Mol Pharm., 10, 4063, 10.1021/mp400426f Augustijns, 2012, Supersaturating drug delivery systems: fast is not necessarily good enough, J Pharm Sci., 101, 7, 10.1002/jps.22750 Bevernage, 2013, Evaluation of gastrointestinal drug supersaturation and precipitation: strategies and issues, Int J Pharm., 453, 25, 10.1016/j.ijpharm.2012.11.026 Bergstrom, 2004, Accuracy of calculated pH-dependent aqueous drug solubility, Eur J Pharm Sci., 22, 387, 10.1016/j.ejps.2004.04.006 Serajuddin, 2007, Salt formation to improve drug solubility, Adv Drug Deliv Rev., 59, 603, 10.1016/j.addr.2007.05.010 Dahan, 2012, The solubility-permeability interplay and its implications in formulation design and development for poorly soluble drugs, AAPS J., 14, 244, 10.1208/s12248-012-9337-6 Narang, 2015, Role of self-association and supersaturation in oral absorption of a poorly soluble weakly basic drug, Pharm Res., 32, 2579 Mantik, 2019, Cyclodextrin reduces intravenous toxicity of a model compound, J Pharm Sci., 108, 1934, 10.1016/j.xphs.2019.01.004 Murdande, 2010, Solubility advantage of amorphous pharmaceuticals: I, A thermodynamic analysis. J Pharm Sci., 99, 1254 Hancock, 2000, What is the true solubility advantage for amorphous pharmaceuticals?, Pharm Res., 17, 397, 10.1023/A:1007516718048 Lindfors, 2006, Amorphous drug nanosuspensions. 2. Experimental determination of bulk monomer concentrations, Langmuir., 22, 911, 10.1021/la052367t Kuentz, 2013, In silico prediction of the solubility advantage for amorphous drugs - are there property-based rules for drug discovery and early pharmaceutical development?, Eur J Pharm Sci., 48, 554, 10.1016/j.ejps.2012.11.015 Luder, 2009, In silico prediction of drug solubility: 4. Will simple potentials suffice?, J Comput Chem., 30, 1859, 10.1002/jcc.21173 Murdande, 2011, Solubility advantage of amorphous pharmaceuticals: part 3: is maximum solubility advantage experimentally attainable and sustainable?, J Pharm Sci., 100, 4349, 10.1002/jps.22643 Manchanda, 2019, Nuances in the calculation of amorphous solubility enhancement ratio, J Pharm Sci., 108, 3560, 10.1016/j.xphs.2019.06.020 Trasi, 2017, Non-sink dissolution behavior and solubility limit of commercial tacrolimus amorphous formulations, J Pharm Sci., 106, 264, 10.1016/j.xphs.2016.09.016 Štukelj, 2019, Direct measurement of amorphous solubility, Anal Chem., 91, 7411, 10.1021/acs.analchem.9b01378 Almeida e Sousa L, Reutzel-Edens SM, Stephenson GA, Taylor LS. Assessment of the amorphous ‘solubility’ of a group of diverse drugs using new experimental and theoretical approaches. Mol Pharm. 2015; 12(2): 484–495. Alsenz, 2007, High throughput solubility measurement in drug discovery and development, Adv Drug Deliv Rev., 59, 546, 10.1016/j.addr.2007.05.007 Könczöl, 2018, Brief overview of solubility methods: recent trends in equilibrium solubility measurement and predictive models, Drug Discov Today: Tech., 27, 3, 10.1016/j.ddtec.2018.06.001 Wyttenbach, 2007, Miniaturized assay for solubility and residual solid screening (SORESOS) in early drug development, Pharm Res., 24, 888, 10.1007/s11095-006-9205-0 Sugano, 2006, High throughput solubility measurement with automated polarized light microscopy analysis, J Pharm Sci., 95, 2115, 10.1002/jps.20628 Macfaul, 2016, On the utility of coupling polarised light microscopy to a solubility assay in drug discovery, J Med Chem Comm., 7, 1123, 10.1039/C6MD00138F Pudipeddi, 2005, Trends in solubility of polymorphs, J Pharm Sci., 94, 929, 10.1002/jps.20302 Saal, 2012, Optimizing solubility: kinetic versus thermodynamic solubility temptations and risks, Eur J Pharm Sci., 47, 589, 10.1016/j.ejps.2012.07.019 Pike, 2020, Optimising proteolysis-targeting chimeras (PROTACs) for oral drug delivery: a drug metabolism and pharmacokinetics perspective, Drug Discov Today., 25, 1793, 10.1016/j.drudis.2020.07.013 Berghausen, 2016, Simulated rat intestinal fluid improves oral exposure prediction for poorly soluble compounds over a wide dose range, ADMET DMPK., 4, 35, 10.5599/admet.4.1.258 Hoelke, 2009, Comparison of nephelometric, UV-spectroscopic, and HPLC methods for high-throughput determination of aqueous drug solubility in microtiter plates, Anal Chem., 81, 3165, 10.1021/ac9000089 Skolnik, 2018, Automated supersaturation stability assay to differentiate poorly soluble compounds in drug discovery, J Pharm Sci., 107, 84, 10.1016/j.xphs.2017.05.025 Zhang, 2020, Preformulation studies and enabling formulation selection for an insoluble compound at preclinical stage—from in vitro, in silico to in vivo, J Pharm Sci., 109, 950, 10.1016/j.xphs.2019.10.023 Plum, 2020, Comparison of induction methods for supersaturation: pH shift versus solvent shift, Int J Pharm., 573, 10.1016/j.ijpharm.2019.118862 Danielson, 2017, In silico ADME techniques used in early-phase drug Discovery, 81 Göller, 2020, Bayer’s in silico ADMET platform: a journey of machine learning over the past two decades, Drug Discov Today., 25, 1702, 10.1016/j.drudis.2020.07.001 Bunally, 2019, Using physicochemical measurements to influence better compound design, SLAS Discov., 24, 791, 10.1177/2472555219859845 Avdeef, 2020, Prediction of aqueous intrinsic solubility of druglike molecules using Random Forest regression trained with Wiki-pS0 database, ADMET DMPK., 8, 29, 10.5599/admet.766 Berghausen, 2014, Diagnosing solubility limitations - the example of hydrate formation, ADMET DMPK., 2, 115, 10.5599/admet.2.2.36 Pissot Soldermann, 2020, Discovery of potent, highly selective, and in vivo efficacious, allosteric MALT1 inhibitors by iterative scaffold morphing, J Med Chem., 63, 14576, 10.1021/acs.jmedchem.0c01245 Faller, 2007, Computational approaches to determine drug solubility, Adv Drug Deliv Rev., 59, 533, 10.1016/j.addr.2007.05.005 Wuelfing, 2015, Preclinical dose number and its application in understanding drug absorption risk and formulation design for preclinical species, Mol Pharm., 12, 1031, 10.1021/mp500504q Butler, 2010, The developability classification system: application of biopharmaceutics concepts to formulation development, J Pharm Sci., 99, 4940, 10.1002/jps.22217 Bayliss, 2016, Quality guidelines for oral drug candidates: dose, solubility and lipophilicity, Drug Discov Today., 21, 1719, 10.1016/j.drudis.2016.07.007 Ding, 2012, Developability assessment of clinical drug products with maximum absorbable doses, Int J Pharm., 427, 260, 10.1016/j.ijpharm.2012.02.003