Oxazolidinone
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Oxazolidinones are a class of azoles, oxazolidines with the carbon between the nitrogen and oxygen oxidized to a ketone, hence oxazolidin - one.
Some of the most important oxazolidinones are the last generation of antibiotics used against gram-positive pathogens, including superbugs such as Staphylococcus aureus. Developed during the nineties when several bacterial strains were becoming resistant against such antibiotics as Vancomycin. These antibiotics are considered as a choice of last resort where every other antibiotic therapy has failed. Linezolid (ZYVOX), the only currently available agent in this class, is available for intravenous administration and also has the advantage of having excellent oral bioavailability.
The first commercially available oxazolidinone antibiotic was Linezolid. In 2002 AstraZeneca introduced the AZD2563 antibiotic. Results indicate that AZD2563 has excellent, targeted activity against all common gram-positive bacteria, regardless of resistance to other classes of antibiotics.
Oxazolidinones are find use as the industrially-important Evans chiral auxiliaries which are used to install stereocenters in organic molecules. The anticoagulant rivaroxaban, an oxazolidinone derivative, is undergoing trials.
