Physicochemical drug properties associated with in vivo toxicological outcomes: a review

Bibliography

• Blagg J. Structure-activity relationships for in vitro and in vivo toxicity. Annu Rep Med Chem 2006;41:353-68
   Web of Science ®Google Scholar
• Kramer JA, Sagartz JE, Morris DL. The application of discovery toxicology and pathology towards the design of safer pharmaceutical lead candidates. Nat Rev Drug Discov 2007;6:636-49
   PubMed Web of Science ®Google Scholar
• Kola I, Landis J. Can the pharmaceutical industry reduce attrition rates? Nat Rev Drug Discov 2004;3:711-5
   PubMed Web of Science ®Google Scholar
• Stevens JL, Baker TK. The future of drug safety testing: expanding the view and narrowing the focus. Drug Discov Today 2009;14:162-7
   PubMed Web of Science ®Google Scholar
• Krejsa CM, Horvath D, Rogalski SL, et al. Predicting ADME properties and side effects: The BioPrint approach. Curr Opin Drug Discov Dev 2003;6(4):470-80
   PubMed Web of Science ®Google Scholar
• Robichaud A, Savoie C, Stamatiou PB, et al. Assessing the emetic potential of PDE4 inhibitors in rats. Br J Pharmacol 2002;135(1):113-8
   PubMed Web of Science ®Google Scholar
• Robichaud A, Savoie C, Stamatiou PB, et al. PDE4 inhibitors induce emesis in ferrets via a noradrenergic pathway. Neuropharmacology 2001;40(2):262-9
   PubMed Web of Science ®Google Scholar
• Boswell-Smith V, Page CP. Roflumilast: a phosphodiesterase-4 inhibitor for the treatment of respiratory disease. Expert Opin Invest Drugs 2006;15(9):1105-13
   PubMed Web of Science ®Google Scholar
• Armour DR, de Groot MJ, Price DA, et al. Overcoming hERG affinity in the discovery of maraviroc; a CCR5 antagonist for the treatment of HIV. Curr Top Med Chem 2008;13:1140-51
   Google Scholar
• Singleton DH, Price DA, Deacon M, et al. Fluorescently labelled analogues of dofetilide as high-affinity fluorescence polarization ligands for the human ether-a-go-go-related gene (hERG) channel. J Med Chem 2007;50:2931-41
   PubMed Web of Science ®Google Scholar
• Kalgutkar AS, Fate G, Didiuk MT, et al. Toxicophores, reactive metabolites and drug safety: when is it a cause for concern? Expert Rev Clin Pharmacol 2008;1(4):515-31
   PubMedGoogle Scholar
• Hop CECA, Kalgutkar AS, Soglia JR. Importance of early assessment of bioactivation in drug discovery. Annu Rep Med Chem 2006;41:369-81
   Web of Science ®Google Scholar
• Williams DP, Naisbitt DJ. Toxicophores: groups and metabolic routes associated with increased safety risk. Curr Opin Drug Discov Dev 2002;5(1):104-15
   PubMed Web of Science ®Google Scholar
• Bender A, Scheiber J, Glick M, et al. Analysis of pharmacology data and the prediction of adverse drug reactions and off-target effects from chemical structure. ChemMedChem 2007;2:861-73
   PubMed Web of Science ®Google Scholar
• Johnson DE, Smith DA, Park KB. Linking toxicity and chemistry: think globally, but act locally? Curr Opin Drug Discov Dev 2004;7(1):33-5
   PubMed Web of Science ®Google Scholar
• Alden CL. The pathologist and toxicologist in pharmaceutical product discovery. Toxicol Pathol 1999;27:104-6
   PubMed Web of Science ®Google Scholar
• MacCoss M, Baillie TA. Organic chemistry in drug discovery. Science 2004;303:1810-3
   PubMed Web of Science ®Google Scholar
• Levine IN. Physical Chemistry. McGraw-Hill publishing; 1978
   Google Scholar
• Atkins PW. Physical Chemistry. Oxford University Press; 1978
   Google Scholar
• Cronin MTD, Zhao YH, Yu RL. pH-dependence and QSAR analysis of the toxicity of phenols and anilines to Daphnia magna. Environ Toxicol 2000;15(2):140-8
   Web of Science ®Google Scholar
• Giolando ST, Rapaport RA, Larson RJ, et al. Environmental fate and effects of DEEDMAC: a new rapidly biodegradable cationic surfactant for use in fabric softeners. Chemosphere 1995;30(6):1067-83
   Web of Science ®Google Scholar
• Monks TJ, Jones DC. The metabolism and toxicity of quinones, quinonimines, quinone methides, and quinine-thioethers. Curr Drug Metab 2002;3:425-38
   PubMedGoogle Scholar
• Cronin MTD. The role of hydrophobicity in toxicity prediction. Curr Comput Aided Drug Des 2006;2:405-13
   Web of Science ®Google Scholar
• Cronin MTD, Livingstone DJ. Predicting Chemical Toxicity and Fate. CRC Press; 2004
   Google Scholar
• Abraham MH, Duce PP, Prior DV, et al. Hydrogen bonding. Part 9. Solute proton-donor and proton-acceptor scales for use in drug design. Perkin Trans 2. J Chem Soc 1989;10:1355-75
   Google Scholar
• Armour DR, de Groot MJ, Price DA, et al. Overcoming HERG affinity in the discovery of the CCR5 antagonist maraviroc. Bio Med Chem Lett 2006;16:4633-7
   PubMed Web of Science ®Google Scholar
• Leeson PD, Springthorpe B. The influence of drug-like concepts on decision making in medicinal chemistry. Nat Rev Drug Discov 2007;6:881-90
   PubMed Web of Science ®Google Scholar
• Keseeru GM, Makara GM. The influence of lead discovery strategies on the properties of drug candidates. Nat Rev Drug Discov 2009;8:203-12
   PubMed Web of Science ®Google Scholar
• Lipinski CA. Drug-like properties and the causes of poor solubility and poor permeability. J Pharmacol Toxicol Methods 2000;44:235-249
   PubMed Web of Science ®Google Scholar
• Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 1997;23:3-25
   Web of Science ®Google Scholar
• Nordqvist A, Nilsson J, Lindmark T, et al. A general model for prediction of Caco-2 cell permeability. QSAR Comb Sci 2004;23(5):303-10
   Google Scholar
• Gleeson MP. Plasma protein binding affinity and its relationship to molecular structure:an in-silico analysis. J Med Chem 2007;50(1):101-12
   PubMed Web of Science ®Google Scholar
• Van de Waterbeemd H, Smith DA, Beaumont K, Walker DK. Property based design:optimisation of drug absorption and pharmacokinetics. J Med Chem 2001;44:1313-1333
   PubMed Web of Science ®Google Scholar
• Siraki AG, Chevaldina T, Moridani MY, O'Brien PJ. Quantitative structure-toxicity relationships by accelerated cytotoxicity mechanism screening. Curr Opin Drug Discov Dev 2004;7(1):118-25
   PubMed Web of Science ®Google Scholar
• Leeson PD, Davis AM. Time related differences in the physical property profiles of oral drugs. J Med Chem 2004;47(25):6338-48
   PubMed Web of Science ®Google Scholar
• Reichert JM. Trends in development and approval times for new therapeutics in the United States. Nat Rev Drug Discov 2003;2:695-702
   PubMed Web of Science ®Google Scholar
• Vieth M, Siegel MG, Higgs RE, et al. Characteristic physical properties and structural fragments of marketed oral drugs. J Med Chem 2004;47(1):224-32
   PubMed Web of Science ®Google Scholar
• Wenlock MC, Austin RP, Barton P, et al. A comparison of physicochemical property profiles of development and marketed drugs. J Med Chem 2003;46:1250-6
   PubMed Web of Science ®Google Scholar
• Proudfoot JR. The evolution of synthetic oral drug properties. Bioorg Med Chem Lett 2005;15:1087-90
   PubMed Web of Science ®Google Scholar
• Hughes JD, Blagg J, Price DA, et al. Physicochemical drug properties associated with in vivo toxicological outcomes. Bioorg Med Chem Lett 2008;18:4872-5
   PubMed Web of Science ®Google Scholar
• Peters JU, Schnider P, Mattei P, Kansy M. Pharmacological promiscuity: dependance on compound properties and target specificity in a set of recent Roche compounds. ChemMedChem 2009; on line publication
   PubMed Web of Science ®Google Scholar
• Azzaoui K, Hamon J, Faller B, et al. Modeling promiscuity based on in vitro safety pharmacology profiling data. ChemMedChem 2007;2:874-80
   PubMed Web of Science ®Google Scholar
• Hopkins AL, Mason JS, Overington JP. Can we rationally design promiscuous drugs? Curr Opin Struct Biol 2006;16:127-36
   PubMed Web of Science ®Google Scholar
• Morphy R, Rankovic Z. The physicochemical challenges of designing multiple ligands. J Med Chem 2006;49:4961-70
   PubMed Web of Science ®Google Scholar
• Roth BL, Sheffler DJ, Kroeze WK. Magic shotguns versus magic bullets: selectively non-selective drugs for mood disorders and schizophrenia. Nat Rev Drug Discov 2004;3(4):353-9
   PubMed Web of Science ®Google Scholar
• Davies MA, Sheffler DJ, Roth BL. Aripiprazole: a novel atypical antipsychotic drug with a uniquely robust pharmacology. CNS Drug Rev 2004;10(4):317-36
   PubMedGoogle Scholar
• LoRusso PM, Eder JP. Therapeutic potential of novel selective-spectrum kinase inhibitors in oncology. Expert Opin Invest Drugs 2008;17(7):1013-28
   PubMed Web of Science ®Google Scholar
• Mestres J, Gregori-Puigjane E, Valverde S, Sole RV. Data completeness-the Achilles heel of drug-target networks. Nat Biotechnol 2008;26(9):983-4
   PubMed Web of Science ®Google Scholar
• Corson TW, Aberle N, Crews CM. Design and applications of bifunctional small molecules: why two heads are better than one. Chem Biol 2008;3(11):677-92
   Google Scholar
• Breiman L. Random forests. Mach Learn 2001;45:5-32
   Web of Science ®Google Scholar
• Chapman D, Buxser S. Effects of membrane partitioning and other physical chemical properties on the apparent potency of “membrane active” compounds evaluated using red blood cell lysis assays. Anal Biochem 2002;303:153-66
   PubMed Web of Science ®Google Scholar
• Reasor MJ, Kacew S. Drug-Induced phospholipidosis: are there functional consequences? Exp Biol Med 2001;226(9):825-30
   PubMed Web of Science ®Google Scholar
• Baronas ET, Lee JW, Alden C, Hsieh FY. Biomarkers to monitor drug-induced phospholipidosis. Toxicol Appl Pharmacol 2007;218(1):72-8
   PubMed Web of Science ®Google Scholar
• Reasor MJ, Hastings KL, Ulrich RG. Drug induced phospholipidosis: issues and future directions. Expert Opin Drug Saf 2006;5:567-83
   PubMed Web of Science ®Google Scholar
• Drenckhahn D, Lullmann-Rauch R. Experimental myopathy induced by amphiphilic cationic compounds including several psychtropic drugs. Neuroscience 1979;4:549-62
   PubMed Web of Science ®Google Scholar
• Agoston M, Orsi F, Feher E, et al. Silymarin and vitamin E reduce amiodarone -induced lysosomal phospholipidosis in rats. Toxicology 2003;190(3):231-41
   PubMed Web of Science ®Google Scholar
• Ploemen JPHTM, Kelder J, Hafmans T, et al. Use of physicochemical calculation of pKa and clogP to predict phospholipidosis-inducing potential. A case study with structurally related piperazines. Exp Toxicol Pathol 2004;55:347-355
   PubMed Web of Science ®Google Scholar
• Tomizawa K, Sugano K, Yamada H, Horii I. Physicochemical and cell-based approach for early screening of phospholipidosis -inducing potential. J Toxicol Sci 2006;31(4):315-24
   PubMedGoogle Scholar
• Peters JU, Hunziker D, Fischer H, et al. An aminomethylpyrimidine DPP-IV inhibitor with improved properties. Bioorg Med Chem Lett 2004;14:3575-8
   PubMed Web of Science ®Google Scholar
• Ruben Z, Dodd DC, Rorig KJ, Anderson SN. Disobutamide: a model agent for investigating intracelular drug storage. Toxicol Appl Pharmacol 1989;97:57-71
   PubMed Web of Science ®Google Scholar
• Hjelle JT, Ruben Z. Investigations in intracellular drug storage:localization of disobutamide in lysosomal and nonlysosomal vesicles. Toxicol Appl Pharmacol 1989;101:70-82
   PubMed Web of Science ®Google Scholar
• Rorig KJ, Ruben Z, Anderson SN. Structural determinants of cationic amphiphilic amines which induce clear cytoplasmic vacuoles in cultured cells. Proc Soc Exp Biol Med 1987;184:165-71
   PubMed Web of Science ®Google Scholar
• Brown AD, Bunnage ME, Glossop PA, et al. The discovery of long acting β2 adrenoreceptor agonists. Bio Med Chem Lett 2007;17:4012-5
   PubMed Web of Science ®Google Scholar
• Nassar AEF, Lopez-Anaya A. Strategies for dealing with reactive intermediates in drug discovery and development. Curr Opin Drug Discov Dev 2004;7(1):126-36
   PubMed Web of Science ®Google Scholar
• Kovacic P, Pozos RS, Somanathan R, et al. Mechanism of mitochondrial uncouplers, inhibitors and toxins: focus on electron transfer, free radicals, and structure activity relationships. Curr Med Chem 2005;12:2601-23
   PubMed Web of Science ®Google Scholar
• Bolton JL, Trush MA, Penning TM, et al. Role of quinones in toxicology. Chem Res Toxicol 2000;13:135-60
   PubMed Web of Science ®Google Scholar
• Doughan A, Dikalov SI. Mitochondrial redox cycling of mitoquinone leads to superoxide production and cellular apoptosis. Antioxidants Redox Signal 2007;9:1825
   PubMed Web of Science ®Google Scholar
• Matkar SS, Wrischnik LA, Hellman-Blumberg U. Production of hydrogen peroxide and redox cycling can explain how sanguinarine and chelerythrine induce apoptosis. Arch Biochem Biophys 2008;477:43
   PubMed Web of Science ®Google Scholar
• Gasbarrini G, Gentiloni N, Febbraro S, et al. Acute liver injury related to the use of niperotidine. J Hepatol 1997;27:583-6
   PubMed Web of Science ®Google Scholar
• Bruneau P, Delvare C, Edwards MP, McMillan RM. Indazolinones, a new series of redox-active 5-lipoxygenase I nhibitors with built-in selectivity and oral activity. J Med Chem 1991;34:1028-36
   PubMed Web of Science ®Google Scholar
• Fort FL, Pratt MC, Carter GW, et al. Heinz bodies, methemoglobinemia, and hemolytic anemia induced in rats by 3-amino-1[m-(trifluoromethyl)phenyl]-2-pyrazoline. Fundam Appl Toxicol 1984;4:216-20
   PubMedGoogle Scholar
• Gould JW, Mercurio MG, Elmets CA. Cutaneous photosensitivity diseases induced by exogenous agents. J Am Acad Dermatol 1995;33(4):551-73
   PubMed Web of Science ®Google Scholar
• Quintero B. Mechanisms of photosensitization induced by drugs: a general survey. Ars Pharm 2000;41(1):27-46
   Google Scholar
• Suter W. Predictive value of in vitro safety studies. Molecular Medicine Triconference, San Francisco 2008
   Google Scholar
• Hansch C, McKarns SC, Smith CJ, Doolittle DJ. Comparative QSAR evidence for a free-radical mechanism of phenol-induced toxicity. Chem Biol Interact 2000;127(1):61-72
   PubMed Web of Science ®Google Scholar
• Garg R, Kurup A, Hansch C. Comparative QSAR: on the toxicology of the phenolic OH moiety. Crit Rev Toxicol 2001;31(2):223-45
   PubMed Web of Science ®Google Scholar
• Benigni R. Structure activity relationship studies of chemical mutagens and carcinogens: mechanistic investigations and prediction approaches. Chem Rev 2005;105(5):1767-800
   PubMed Web of Science ®Google Scholar
• Hatch FT, Knize MG, Colvin ME. Extended quantitative structure-activity relationships for 80 aromatic and heterocyclic amines: structural, electronic and hydropathic factors effecting mutagenic potency. Environ Mol Mutag 2001;38:268-91
   PubMed Web of Science ®Google Scholar
• Argese E, Bettiol C, Giurin G, Miana P. Quantitative structure-activity relationships for the toxicity of chlorophenols to mammalian submitochondrial particles. Chemosphere 1999;38(10):2281-92
   PubMed Web of Science ®Google Scholar
• Siraki AG, Chevaldina T, O'Brien PJ. Application of quantitative structure-toxicity relationships for acute NSAID cytotoxicity in rat hepatocytes. Chem Biol Interact 2005;151(3):177-91
   PubMed Web of Science ®Google Scholar
• Sasseville VG, Lane JH, Kadambi VJ, et al. Testing paradigm for prediction of development-limiting barriers and human drug toxicity. Chem Biol Interact 2004;150(1):9-25
   PubMed Web of Science ®Google Scholar
• Alden C, Lin L, Smith P. Predictive toxicology technology for avoiding idiosyncratic liver injury. Preclinica 2003;27-35
   Google Scholar
• Olson H, Betton G, Robinson D, et al. Concordance of the toxicity of pharmaceuticals in humans and in animals. Regul Toxicol Pharm 2000;32(1):56-67
   PubMed Web of Science ®Google Scholar
• Greaves P, Williams A, Eve M. First dose of potential new medicines to humans: how animals help. Nat Rev Drug Discov 2004;3:226-36
   PubMed Web of Science ®Google Scholar
• Broadhead CL, Betton G, Combes R, et al. Prospects for reducing and refining the use of dogs in the regulatory toxicity testing of pharmaceuticals. Hum Exp Toxicol 2000;19(8):440-7
   PubMed Web of Science ®Google Scholar
• Evans SM, Casartelli A, Herreros E, et al. Development of a high throughput in vitro toxicity screen predictive of high acute in vivo toxic potential. Toxicol In Vitro 2001;15(4/5):579-84
   PubMed Web of Science ®Google Scholar
• Walum E, Hedander J, Garberg P. Research perspectives for pre-screening alternatives to animal experimentation. Toxicol Appl Pharmacol 2005;207(2):S393-S397
   PubMedGoogle Scholar