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Ceftaroline fosamil (Molecule of the Month for December 2009)

Teflaro



Ceftaroline fosamil (brand name Teflaro) is an advanced generation cephalosporin antibiotic. It is active against methicillin-resistant Staphylococcus aureus (MRSA) and Gram positive bacteria. It retains the activity of later generation cephalosporins having broad spectrum activity against Gram negative bacteria. It is currently being investigated for community-acquired pneumonia and complicated skin and skin structure infection. Ceftaroline is being developed by Forest Laboratories, under a license from Takeda. Ceftaroline has received approval from the U.S. Food and Drug Administration for the treatment of community-acquired bacterial pneumonia and acute bacterial skin infections on October 29, 2010.[6] In vitro studies show that it has a similar spectrum to ceftobiprole, the only other fifth-generation cephalosporin to date, although no head to head clinical trials have been conducted. Currently, ceftaroline and ceftobiprole are on an unnamed subclass of cephalosporins by the Clinical and Laboratory Standards Institute (CLSI).

Beta-lactam antibiotics inhibit bacterial peptidoglycan synthesis by binding the penicillin binding proteins (PBPs) in the bacterial cell wall. Inhibition of PBPs leads to irregularities in cell wall structures, such as elongation, lesions, loss of selective permeability, and eventual cell death and lysis. In particular, ceftaroline can effectively bind to and inhibit PBP-2a, the type of PBP produced by MRSA and not well inhibited by other antibiotics currently in clinical use.Ceftaroline is a novel cephalosporin that has activity against MRSA with phase III clinical trials for complicated skin and skin structure infections with reported non-inferior efficacy against MRSA compared to vancomycin and aztreonam.

Serious hypersensitivity (anaphylactic) reactions and serious skin reactions have been reported with beta-lactam antibiotics, including ceftaroline. Exercise caution in patients with known hypersensitivity to beta-lactam antibiotics including ceftaroline. Before therapy with ceftaroline is instituted, careful inquiry about previous hypersensitivity reactions to other cephalosporins, penicillins, or carbapenems should be made. If this product is to be given to penicillin or other beta-lactam-allergic patient, caution should be exercised because cross sensitivity among beta-lactam antibacterial agents has been clearly established. If an allergic reaction to ceftaroline occurs, the drug should be discontinued.

Formal Chemical Name (IUPAC)

References

http://en.wikipedia.org/wiki/Ceftaroline_fosamil

Picture of Ceftaroline fosamil 3D model

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Picture of Ceftaroline fosamil

C24 H25 N8 O10 P S4



Update by Karl Harrison
(Molecule of the Month for December 2009 )

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