Properties of FDA-approved small molecule protein kinase inhibitors: A 2020 update

Pharmacological Research - Tập 152 - Trang 104609 - 2020
Robert Roskoski1
1Blue Ridge Institute for Medical Research, 3754 Brevard Road, Suite 116, Box 19, Horse Shoe, North Carolina 28742-8814, United States

Tài liệu tham khảo

Roskoski, 2015, A historical overview of protein kinases and their targeted small molecule inhibitors, Pharmacol. Res., 100, 1, 10.1016/j.phrs.2015.07.010 Cohen, 2002, Protein kinases – the major drug targets of the twenty-first century?, Nat. Rev. Drug Discov., 1, 309, 10.1038/nrd773 Kanev, 2019, The landscape of atypical and eukaryotic protein kinases, Trends Pharmacol. Sci., 40, 818, 10.1016/j.tips.2019.09.002 Carles, 2018, PKIDB: a curated, annotated and updated database of protein kinase inhibitors in clinical trials, Molecules, 23, 10.3390/molecules23040908 Fischer, 2017, Approved and experimental small-molecule oncology kinase inhibitor drugs: a mid-2016 overview, Med. Res. Rev., 37, 314, 10.1002/med.21409 Manning, 2002, The protein kinase complement of the human genome, Science, 298, 1912, 10.1126/science.1075762 Myers, 2016, AXL inhibitors in cancer: a medicinal chemistry perspective, J. Med. Chem., 59, 3593, 10.1021/acs.jmedchem.5b01273 Roth, 2004, Magic shotguns versus magic bullets: selectively non-selective drugs for mood disorders and schizophrenia, Nat. Rev. Drug Discov., 3, 353, 10.1038/nrd1346 Roskoski, 2019, Properties of FDA-approved small molecule protein kinase inhibitors, Pharmacol. Res., 144, 19, 10.1016/j.phrs.2019.03.006 Knighton, 1991, Crystal structure of the catalytic subunit of cyclic adenosine monophosphate-dependent protein kinase, Science, 253, 407, 10.1126/science.1862342 Knighton, 1991, Structure of a peptide inhibitor bound to the catalytic subunit of cyclic adenosine monophosphate-dependent protein kinase, Science, 253, 414, 10.1126/science.1862343 Taylor, 2011, Protein kinases: evolution of dynamic regulatory proteins, Trends Biochem. Sci., 36, 65, 10.1016/j.tibs.2010.09.006 Kornev, 2015, Dynamics-driven allostery in protein kinases, Trends Biochem. Sci., 40, 628, 10.1016/j.tibs.2015.09.002 Roskoski, 2019, Cyclin-dependent protein serine/threonine kinase inhibitors as anticancer drugs, Pharmacol. Res., 139, 471, 10.1016/j.phrs.2018.11.035 Hanks, 1995, Protein kinases 6. The eukaryotic protein kinase superfamily: kinase (catalytic) domain structure and classification, FASEB J., 9, 576, 10.1096/fasebj.9.8.7768349 Madhusudan, 1994, cAMP-dependent protein kinase: crystallographic insights into substrate recognition and phosphotransfer, Protein Sci., 3, 176, 10.1002/pro.5560030203 Zhou, 1997, Participation of ADP dissociation in the rate-determining step in cAMP-dependent protein kinase, Biochemistry, 36, 15733, 10.1021/bi971438n Schwartz, 2011, Protein kinase biochemistry and drug discovery, Bioorg. Chem., 39, 192, 10.1016/j.bioorg.2011.07.004 Kornev, 2010, Defining the conserved internal architecture of a protein kinase, Biochim. Biophys. Acta, 1804, 440, 10.1016/j.bbapap.2009.10.017 Kornev, 2006, Surface comparison of active and inactive protein kinases identifies a conserved activation mechanism, Proc. Natl. Acad. Sci. U. S. A., 103, 17783, 10.1073/pnas.0607656103 Kornev, 2008, A helix scaffold for the assembly of active protein kinases, Proc. Natl. Acad. Sci. U. S. A., 105, 14377, 10.1073/pnas.0807988105 Meharena, 2013, Deciphering the structural basis of eukaryotic protein kinase regulation, PLoS Biol., 11, 10.1371/journal.pbio.1001680 Roskoski, 2016, Classification of small molecule protein kinase inhibitors based upon the structures of their drug-enzyme complexes, Pharmacol. Res., 103, 26, 10.1016/j.phrs.2015.10.021 Roskoski, 2014, The ErbB/HER family of protein-tyrosine kinases and cancer, Pharmacol. Res., 79, 34, 10.1016/j.phrs.2013.11.002 Roskoski, 2014, ErbB/HER protein-tyrosine kinases: structures and small molecule inhibitors, Pharmacol. Res., 87, 42, 10.1016/j.phrs.2014.06.001 Roskoski, 2019, Small molecule inhibitors targeting the EGFR/ErbB family of protein-tyrosine kinases in human cancers, Pharmacol. Res., 139, 395, 10.1016/j.phrs.2018.11.014 Roskoski, 2018, The role of small molecule platelet-derived growth factor receptor (PDGFR) inhibitors in the treatment of neoplastic disorders, Pharmacol. Res., 129, 65, 10.1016/j.phrs.2018.01.021 Roskoski, 2017, Vascular endothelial growth factor (VEGF) and VEGF receptor inhibitors in the treatment of renal cell carcinomas, Pharmacol. Res., 120, 116, 10.1016/j.phrs.2017.03.010 Roskoski, 2018, The role of small molecule Kit protein-tyrosine kinase inhibitors in the treatment of neoplastic disorders, Pharmacol. Res., 133, 35, 10.1016/j.phrs.2018.04.020 Roskoski, 2017, ROS1 protein-tyrosine kinase inhibitors in the treatment of ROS1 fusion protein-driven non-small cell lung cancers, Pharmacol. Res., 121, 202, 10.1016/j.phrs.2017.04.022 Roskoski, 2018, Role of RET protein-tyrosine kinase inhibitors in the treatment RET-driven thyroid and lung cancers, Pharmacol. Res., 128, 1, 10.1016/j.phrs.2017.12.021 Roskoski, 2013, Anaplastic lymphoma kinase (ALK): structure, oncogenic activation, and pharmacological inhibition, Pharmacol. Res., 68, 68, 10.1016/j.phrs.2012.11.007 Roskoski, 2017, Anaplastic lymphoma kinase (ALK) inhibitors in the treatment of ALK-driven lung cancers, Pharmacol. Res., 117, 343, 10.1016/j.phrs.2017.01.007 Roskoski, 2020, The role of fibroblast growth factor receptor (FGFR) protein-tyrosine kinase inhibitors in the treatment of cancers including those of the urinary bladder, Pharmacol. Res., 151, 10.1016/j.phrs.2019.104567 Roskoski, 2016, Janus kinase (JAK) inhibitors in the treatment of inflammatory and neoplastic diseases, Pharmacol. Res., 111, 784, 10.1016/j.phrs.2016.07.038 Roskoski, 2016, Cyclin-dependent protein kinase inhibitors including palbociclib as anticancer drugs, Pharmacol. Res., 107, 249, 10.1016/j.phrs.2016.03.012 Roskoski, 2018, Targeting oncogenic Raf protein-serine/threonine kinases in human cancers, Pharmacol. Res., 135, 239, 10.1016/j.phrs.2018.08.013 Roskoski, 2012, ERK1/2 MAP kinases: structure, function, and regulation, Pharmacol. Res., 66, 105, 10.1016/j.phrs.2012.04.005 Roskoski, 2019, Targeting ERK1/2 protein-serine/threonine kinases in human cancers, Pharmacol. Res., 142, 151, 10.1016/j.phrs.2019.01.039 Roskoski, 2017, Allosteric MEK1/2 inhibitors including cobimetanib and trametinib in the treatment of cutaneous melanomas, Pharmacol. Res., 117, 20, 10.1016/j.phrs.2016.12.009 Roskoski, 2015, Src protein-tyrosine kinase structure, mechanism, and small molecule inhibitors, Pharmacol. Res., 94, 9, 10.1016/j.phrs.2015.01.003 Liu, 1998, A molecular gate which controls unnatural ATP analogue recognition by the tyrosine kinase v-Src, Bioorg. Med. Chem., 6, 1219, 10.1016/S0968-0896(98)00099-6 Dar, 2011, The evolution of protein kinase inhibitors from antagonists to agonists of cellular signaling, Annu. Rev. Biochem., 80, 769, 10.1146/annurev-biochem-090308-173656 Ung, 2018, Redefining the protein kinase conformational space with machine learning, Cell Chem. Biol., 25, 10.1016/j.chembiol.2018.05.002 Zuccotto, 2010, Through the "gatekeeper door": exploiting the active kinase conformation, J. Med. Chem., 53, 2691, 10.1021/jm901443h Gavrin, 2013, Approaches to discover non-ATP site inhibitors, Med. Chem. Res., 4, 41 Lamba, 2012, New directions in targeting protein kinases: focusing upon true allosteric and bivalent inhibitors, Curr. Pharm. Des., 18, 2936, 10.2174/138161212800672813 Johnson, 2016, Bivalent inhibitors of c-Src tyrosine kinase that bind a regulatory domain, Bioconjug. Chem., 27, 1745, 10.1021/acs.bioconjchem.6b00243 Copeland, 2016, The drug-target residence time model: a 10-year retrospective, Nat. Rev. Drug Discov., 15, 87, 10.1038/nrd.2015.18 van Linden, 2014, KLIFS: a knowledge-based structural database to navigate kinase-ligand interaction space, J. Med. Chem., 57, 249, 10.1021/jm400378w Liao, 2007, Molecular recognition of protein kinase binding pockets for design of potent and selective kinase inhibitors, J. Med. Chem., 50, 409, 10.1021/jm0608107 Kooistra, 2017, Kinase-centric computational drug development, Ann Rep Med Chem, 50, 197 Bajusz, 2017, Structure-based virtual screening approaches in kinase-directed drug discovery, Curr. Top. Med. Chem., 17, 2235, 10.2174/1568026617666170224121313 Wu, 2015, FDA-approved small-molecule kinase inhibitors, Trends Pharmacol. Sci., 36, 422, 10.1016/j.tips.2015.04.005 Lipinski, 2001, Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Deliv. Rev., 46, 3, 10.1016/S0169-409X(00)00129-0 Menichincheri, 2016, Discovery of entrectinib: a new 3-aminoindazole as a potent anaplastic lymphoma kinase (ALK), c-ros oncogene 1 kinase (ROS1), and pan-tropomyosin receptor kinases (pan-TRKs) inhibitor, J. Med. Chem., 59, 3392, 10.1021/acs.jmedchem.6b00064 No authors listed. Entrectinib OK’d for cancers with NTRK fusions, NSCLC. Cancer Discov. 2019;9:OF2. doi: 10.1158/2159-8290.CD-NB2019-101. Cocco, 2018, NTRK fusion-positive cancers and TRK inhibitor therapy, Nat. Rev. Clin. Oncol., 15, 731, 10.1038/s41571-018-0113-0 Solomon, 2019, NTRK fusion detection across multiple assays and 33,997 cases: diagnostic implications and pitfalls, Mod. Pathol. Al-Salama, 2019, Entrectinib: first global approval, Drugs, 79, 1477, 10.1007/s40265-019-01177-y Scott, 2019, Larotrectinib: first global approval, Drugs Drilon, 2018, Efficacy of larotrectinib in TRK fusion-positive cancers in adults and children, N. Engl. J. Med., 378, 731, 10.1056/NEJMoa1714448 Loriot, 2019, Erdafitinib in locally advanced or metastatic urothelial carcinoma, N. Engl. J. Med., 381, 338, 10.1056/NEJMoa1817323 Hanna, 2019, Erdafitinib to treat urothelial carcinoma, Drugs Today, 55, 495, 10.1358/dot.2019.55.8.3010573 Patani, 2016, Landscape of activating cancer mutations in FGFR kinases and their differential responses to inhibitors in clinical use, Oncotarget, 7, 24252, 10.18632/oncotarget.8132 Dienstmann, 2014, Genomic aberrations in the FGFR pathway: opportunities for targeted therapies in solid tumors, Ann. Oncol., 25, 552, 10.1093/annonc/mdt419 Gattineni, 2014, Regulation of renal phosphate transport by FGF23 is mediated by FGFR1 and FGFR4, Am. J. Physiol. Renal Physiol., 306, 10.1152/ajprenal.00232.2013 Kim, 2019, First-in-human phase I study of fisogatinib (BLU-554) validates aberrant fibroblast growth factor 19 signaling as a driver event in hepatocellular carcinoma, Cancer Discov., 10.1158/2159-8290.CD-19-0555 Han, 2016, Conditional deletion of Fgfr1 in the proximal and distal tubule identifies distinct roles in phosphate and calcium transport, PLoS One, 11, 10.1371/journal.pone.0147845 Facchinetti, 2019, Facts and new hopes on selective FGFR inhibitors in solid tumors, Clin. Cancer Res., 10.1158/1078-0432.CCR-19-2035 Lamb, 2019, Pexidartinib: first approval, Drugs Tap, 2019, Pexidartinib versus placebo for advanced tenosynovial giant cell tumour (ENLIVEN): a randomised phase 3 trial, Lancet, 394, 478, 10.1016/S0140-6736(19)30764-0 Tap, 2015, Structure-guided blockade of CSF1R kinase in tenosynovial giant-cell tumor, N. Engl. J. Med., 373, 428, 10.1056/NEJMoa1411366 Blair, 2019, Fedratinib: first approval, Drugs, 79, 1719, 10.1007/s40265-019-01205-x Pardanani, 2011, Safety and efficacy of TG101348, a selective JAK2 inhibitor, in myelofibrosis, J. Clin. Oncol., 29, 789, 10.1200/JCO.2010.32.8021 Ciceri, 2014, Dual kinase-bromodomain inhibitors for rationally designed polypharmacology, Nat. Chem. Biol., 10, 305, 10.1038/nchembio.1471 Sahni, 2018, Targeting bromodomain and extraterminal proteins in breast cancer, Pharmacol. Res., 129, 156, 10.1016/j.phrs.2017.11.015 Siu, 2013, 2-Amino-[1,2,4]triazolo[1,5-a]pyridines as JAK2 inhibitors, Bioorg. Med. Chem. Lett., 23, 5014, 10.1016/j.bmcl.2013.06.008 Hopkins, 2004, Ligand efficiency: a useful metric for lead selection, Drug Discov. Today, 9, 430, 10.1016/S1359-6446(04)03069-7 Smith, 2009, Medicinal chemistry by the numbers: the physicochemistry, thermodynamics and kinetics of modern drug design, Prog. Med. Chem., 48, 1, 10.1016/S0079-6468(09)04801-2 Leeson, 2007, The influence of drug-like concepts on decision-making in medicinal chemistry, Nat. Rev. Drug Discov., 6, 881, 10.1038/nrd2445 Ekins, 2016, Thermodynamic proxies to compensate for biases in drug discovery methods, Pharm. Res., 33, 194, 10.1007/s11095-015-1779-y Hopkins, 2014, The role of ligand efficiency metrics in drug discovery, Nat. Rev. Drug Discov., 13, 105, 10.1038/nrd4163 Leeson, 2016, Molecular inflation, attrition, and the rule of five, Adv. Drug Deliv. Rev., 101, 22, 10.1016/j.addr.2016.01.018 Veber, 2002, Molecular properties that influence the oral bioavailability of drug candidates, J. Med. Chem., 45, 2615, 10.1021/jm020017n Oprea, 2000, Property distribution of drug-related chemical databases, J. Comput. Aided Mol. Des., 14, 251, 10.1023/A:1008130001697 Bertz, 1981, The first general index of molecular complexity, J. Am. Chem. Soc., 1103, 3559 Hendrickson, 1987, Molecular complexity: a simplified formula adapted to individual atoms, J Chem Inf Compout Sci, 27, 63, 10.1021/ci00054a004 Bechman, 2019, The new entries in the therapeutic armamentarium: the small molecule JAK inhibitors, Pharmacol. Res., 147, 10.1016/j.phrs.2019.104392 K. Bechman, G.B. Galloway, K.L. Winthrop, Small-molecule protein kinase inhibitors and the risk of fungal infections. Curr. Fungal Infect. Rep. https://doi.org/10.1007/s12281-019-00350-w. Kantarjian, 2013, Cancer drugs in the United States: justum pretium–the just price, J. Clin. Oncol., 31, 3600, 10.1200/JCO.2013.49.1845 Smalley, 2019, Pharmacological research and cancer: a call to arms, Pharmacol. Res., 146, 10.1016/j.phrs.2019.104291 Yezefski, 2018, Patient assistance programs: a valuable, yet imperfect, way to ease the financial toxicity of cancer care, Semin. Hematol., 55, 185, 10.1053/j.seminhematol.2017.07.004 Kesselheim, 2016, The high cost of prescription drugs in the United States: origins and prospects for reform, JAMA, 316, 858, 10.1001/jama.2016.11237 Papanicolas, 2018, Health care spending in the United States and other high-income countries, JAMA, 319, 1024, 10.1001/jama.2018.1150 Zafar, 2013, The financial toxicity of cancer treatment: a pilot study assessing out-of-pocket expenses and the insured cancer patient’s experience, Oncologist, 18, 381, 10.1634/theoncologist.2012-0279 Dusetzina, 2014, Cost sharing and adherence to tyrosine kinase inhibitors for patients with chronic myeloid leukemia, J. Clin. Oncol., 32, 306, 10.1200/JCO.2013.52.9123 Gilligan, 2018, Death or debt? National estimates of financial toxicity in persons with newly-diagnosed cancer, Am. J. Med., 131, 1187, 10.1016/j.amjmed.2018.05.020 Roskoski, 2017, Guidelines for preparing color figures for everyone including the colorblind, Pharmacol. Res., 119, 240, 10.1016/j.phrs.2017.02.005