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• W2279263454 abstract "Key to the pharmaceutical utility of certain macrocyclic drugs is a 'chameleonic' ability to change their conformation to expose polar groups in aqueous solution, but bury them when traversing lipid membranes. Based on analysis of the structures of 20 macrocyclic compounds that are approved oral drugs, we propose that good solubility requires a topological polar surface area (TPSA, in Å(2)) of ≥0.2×molecular weight (MW). Meanwhile, good passive membrane permeability requires a molecular (i.e., 3D) PSA in nonpolar environments of ≤140Å(2). We show that one or other of these limits is almost invariably violated for compounds with MW>600Da, suggesting that some degree of chameleonic behavior is required for most high MW oral drugs." @default.
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• W2279263454 date "2016-05-01" @default.
• W2279263454 modified "2023-10-18" @default.
• W2279263454 title "Quantifying the chameleonic properties of macrocycles and other high-molecular-weight drugs" @default.
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• W2279263454 doi "https://doi.org/10.1016/j.drudis.2016.02.005" @default.
• W2279263454 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/5821503" @default.
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