2-oxazolidone 2-oxazolidone 2-oxazolidone is a heterocyclic organic compound containing both nitrogen and oxygen in a 5-membered ring. 2-oxazolidone names preferred iupac name 1,3-oxazolidin-2-one other names 2-oxazolidone2-oxazolidinone identifiers cas number 497-25-6 y 3d model (jsmol) interactive image chemspider 66579 y echa infocard 100.007.129 kegg c06695 y pubchem cid 73949 unii z4d49w92pp y comptox dashboard (epa) dtxsid2074326 inchi inchi=1s/c3h5no2/c5-3-4-1-2-6-3/h1-2h2,(h,4,5) ykey: izxiztknffyfof-uhfffaoysa-n yinchi=1/c3h5no2/c5-3-4-1-2-6-3/h1-2h2,(h,4,5)key: izxiztknffyfof-uhfffaoyae smiles o=c1occn1 properties chemical formula c3h5no2 molar mass 87.077 g/mol appearance solid melting point 86 to 89 °c (187 to 192 °f; 359 to 362 k) boiling point 220 °c (428 °f; 493 k) at 48 torr related compounds related compounds oxazolidine except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). y verify (what is yn ?) infobox references oxazolidinones evans auxiliaries oxazolidinones are a class of compounds containing 2-oxazolidone in the structure. in chemistry, they are useful as evans auxiliaries, which are used for chiral synthesis. usually, the acid chloride substrate reacts with the oxazolidinone to form an imide. substituents at the 4 and 5 position of the oxazolidinone direct any aldol reaction to the alpha position of the carbonyl of the substrate. pharmaceuticals oxazolidinones are mainly used as antimicrobials. the antibacterial effect of oxazolidinones is by working as protein synthesis inhibitors, targeting an early step involving the binding of n-formylmethionyl-trna to the ribosome. (see linezolid#pharmacodynamics) some of the most important oxazolidinones are antibiotics. examples of antibiotic oxazolidinones include: linezolid (zyvox), which is available for intravenous administration and also has the advantage of having excellent oral bioavailability. posizolid, which appears to have excellent, targeted bactericidal activity against all common gram-positive bacteria, regardless of resistance to other classes of antibiotics. chemical structure of tedizolid tedizolid, (sivextro) which is approved for acute skin infections radezolid (rx-1741) has completed some phase-ii clinical trials. cycloserine is a second line drug against tuberculosis. note that cycloserine, while technically an oxazolidone, has a different mechanism of action and substantially different properties from the aforementioned compounds. contezolid (s)-5-((isoxazol-3-ylamino)methyl)-3-(2,3,5-trifluoro-4-(4-oxo-3,4-dihydropyridin-1(2h)-yl)phenyl)oxazolidin-2-one (mrx-i) has reported phase 1 data and phase iii data (ref journal of antimicrobial chemotherapy, volume 77, issue 6, june 2022, pages 1762–1769, https://doi.org/10.1093/jac/dkac073). in 2021, a new drug summary was published by adis press (ref:https://link.springer.com/article/10.1007/s40265-021-01576-0). in june 2021, marketing approval was granted by the chinese national medical products administration (nmpa) for use of oral contezolid in moderate to severe complicated skin and skin structure infections (http://www.micurx.com/703.html). in june 2022, contezolid oral tablets and contezolid acefosamil iv (prodrug for contezolid) began phase 3 global clinical trials in moderate to severe diabetic foot infections. (clinicaltrials.gov identifier: nct05369052). an additional global phase 3 study is planned for acute bacterial skin and skin structure infections (absssi) for the combination of contezolid and contezolid acefosamil. an oxazolidinone derivative used for other purposes is rivaroxaban, which is approved by the fda for venous thromboembolism prophylaxis. history chemical structure of cycloserine the first ever used oxazolidinone was cycloserine (4-amino-1,2-oxazolidin-3-one), a second line drug against tuberculosis since 1956. developed during the nineties when several bacterial strains were becoming resistant against such antibiotics as vancomycin. linezolid (zyvox) is the first approved agent in the class (fda approval april 2000). chemical structure of linezolid the first commercially available 1,3-oxazolidinone antibiotic was linezolid, discovered and developed by pharmacia & upjohn. chemical structure of posizolid/azd2563 in 2002 astrazeneca began investigating posizolid, which is in clinical trials for use in humans.