Antibacterial oxazolidinones possessing a novel C-5 side chain. (5R)-trans-3-[3-Fluoro-4- (1-oxotetrahydrothiopyran-4-yl)phenyl]-2- oxooxazolidine-5-carboxylic acid amide (PF-00422602), a new lead compound.

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Poel TJ, Thomas RC, Adams WJ, Aristoff PA, Barbachyn MR, Boyer FE, Brieland J, Brideau R, Brodfuehrer J, Brown AP, Choy AL, Dermyer M, Dority M, Ford CW, Gadwood RC, Hanna D, Hongliang C, Huband MD, Huber C, Kelly R, Kim JY, Martin JP Jr, Pagano PJ, Ross D, Skerlos L, Sulavik MC, Zhu T, Zurenko GE, Prasad JV

Antibacterial oxazolidinones possessing a novel C-5 side chain. (5R)-trans-3-[3-Fluoro-4- (1-oxotetrahydrothiopyran-4-yl)phenyl]-2- oxooxazolidine-5-carboxylic acid amide (PF-00422602), a new lead compound.

J Med Chem. 2007 Nov 29;50(24):5886-9. Epub 2007 Nov 8.

PubMed ID
17988109 [ View in PubMed
]
Abstract

Oxazolidinones possessing a C-5 carboxamide functionality (reverse amides) represent a new series of compounds that block bacterial protein synthesis. These reverse amides also exhibited less potency against monoamine oxidase (MAO) enzymes and thus possess less potential for the side effects associated with MAO inhibition. The title compound (14) showed reduced in vivo myelotoxicity compared to linezolid in a 14-day safety study in rats, potent in vivo efficacy in murine systemic infection models, and excellent pharmacokinetic properties.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
LinezolidAmine oxidase [flavin-containing] AKi (nM)53000N/AN/ADetails