2-Oxazolidone

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2-Oxazolidone
2-Oxazolidone.png Oxazolidin-2-one-3D-balls.png
Identifiers
CAS number 497-25-6 YesY
PubChem 73949
ChemSpider 66579 YesY
KEGG C06695 YesY
Jmol-3D images Image 1
Properties
Molecular formula C3H5NO2
Molar mass 87.077 g/mol
Appearance Solid
Melting point 86–89 °C
Boiling point 220 °C at 48 torr
Related compounds
Related compounds Oxazolidine
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

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

Oxazolidinones[edit]

Evans auxiliaries[edit]

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[edit]

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.[1]

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.[citation needed]

Examples of antibiotic oxazolidinones include:

  • Linezolid (Linox), 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 torezolid

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

History[edit]

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.[3] 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.


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).

References[edit]

  1. ^ Shinabarger, D. (1999). "Mechanism of action of the oxazolidinone antibacterial agents". Expert Opinion on Investigational Drugs 8 (8): 1195–1202. doi:10.1517/13543784.8.8.1195. PMID 15992144.  edit
  2. ^ "Rx 1741". Rib-X Pharmaceuticals. 2009. Retrieved 2009-05-17. 
  3. ^ 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[edit]