Wed . 19 Jun 2019


2-Oxazolidone is a heterocyclic organic compound containing both nitrogen and oxygen in a 5-membered ring


  • 1 Oxazolidinones
    • 11 Evans auxiliaries
    • 12 Pharmaceuticals
      • 121 History
  • 2 See also
  • 3 References
  • 4 External links


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


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#Mechanism of action

Some of the most important oxazolidinones are the last generation of antibiotics used against gram-positive pathogens, including superbugs such as methicillin-resistant Staphylococcus aureus These antibiotics are considered as a choice of last resort where every other antibiotic therapy has failed

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
  • S-5-isoxazol-3-ylaminomethyl-3-2,3,5-trifluoro-4-4-oxo-3,4-dihydropyridin-12H-ylphenyloxazolidin-2-one MRX-I has reported phase 1 data and completed phase II trials in 2015, and is starting a phase 3 trial in 2016

An oxazolidinone derivative used for other purposes is rivaroxaban, which is approved by the FDA for venous thromboembolism prophylaxis


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 introduced posizolid AZD2563

See also

  • Oxazolidine - the ring without the carbonyl group
  • Oxazolone - the unsaturated analogues


  1. ^ Shinabarger, D 1999 "Mechanism of action of the oxazolidinone antibacterial agents" Expert Opinion on Investigational Drugs 8 8: 1195–1202 doi:101517/13543784881195 PMID 15992144 
  2. ^ Wookey, A; Turner, P J; Greenhalgh, J M; Eastwood, M; Clarke, J; Sefton, C 2004 "AZD2563, a novel oxazolidinone: definition of antibacterial spectrum, assessment of bactericidal potential and the impact of miscellaneous factors on activity in vitro" Clinical Microbiology and Infection 10 3: 247–254 doi:101111/j1198-743X200400770x PMID 15008947 
  3. ^ "Rx 1741" Rib-X Pharmaceuticals 2009 Archived from the original on 2009-02-26 Retrieved 2009-05-17 
  4. ^ Gordeev, Mikhail F; Yuan, Zhengyu Y 2014 "New Potent Antibacterial Oxazolidinone MRX-I with an Improved Class Safety Profile" Journal of Medicinal Chemistry 57 11: 4487–4497 doi:101021/jm401931e 
  5. ^ MicuRx Initiates Phase 3 Clinical Trial for MRX-I 2016
  6. ^ A W Frahm, H H J Hager, F v Bruchhausen, M Albinus, H Hager: Hagers Handbuch der pharmazeutischen Praxis: Folgeband 4: Stoffe A-K, Birkhäuser, 1999, ISBN 978-3-540-52688-9

External links

  • Synthesis of Oxazolidinones - Recent Literature


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