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Drug Discov Today. 2009 Nov;14(21-22):1011-20. doi: 10.1016/j.drudis.2009.07.014. Epub 2009 Sep 1.

The impact of aromatic ring count on compound developability--are too many aromatic rings a liability in drug design?

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  • 1Respiratory CEDD, GlaxoSmithKline Research Medicines Centre, Gunnels Wood Road, Stevenage SG1 2NY, UK.

Abstract

The impact of aromatic ring count (the number of aromatic and heteroaromatic rings) in molecules has been analyzed against various developability parameters - aqueous solubility, lipophilicity, serum albumin binding, CyP450 inhibition and hERG inhibition. On the basis of this analysis, it was concluded that the fewer aromatic rings contained in an oral drug candidate, the more developable that candidate is probably to be; in addition, more than three aromatic rings in a molecule correlates with poorer compound developability and, thus, an increased risk of attrition in development. Data are also presented that demonstrate that even within a defined lipophilicity range, increased aromatic ring count leads to decreased aqueous solubility.

PMID:
19729075
[PubMed - indexed for MEDLINE]
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