Ceftobiprole

Ceftobiprole

Drugbox
IUPAC_name = (6R,7R)-7- [(2Z)-2-(5-amino-1,2,4-thiadiazol-3-ylidene)- 2-nitroso-1-oxoethyl] amino] -8-oxo-3- [(E)- [2-oxo-1- [(3R)- 3-pyrrolidinyl] -3-pyrrolidinylidene] methyl] -5-thia-1- azabicyclo [4.2.0] oct-2-ene-2-carboxylic acid


CAS_number = 209467-52-7
CAS_supplemental = CAS|252188-71-9 (medocaril)
ATC_prefix = J01
ATC_suffix = DI01
ATC_supplemental = [cite web |url=http://www.whocc.no/atcddd/new_atc_ddd.html#ATCDDD_FINAL |title=ATC/DDD Classification (FINAL): New ATC 5th level codes |date=August 27, 2008 |author=WHO International Working Group for Drug Statistics Methodology |publisher=WHO Collaborating Centre for Drug Statistics Methodology |accessdate=2008-09-05]
PubChem = 6918430
DrugBank =
C=20 | H=22 | N=8 | O=6 | S=2
molecular_weight = 534.568 g/mol
bioavailability =
protein_bound =
metabolism =
elimination_half-life =
excretion =
pregnancy_AU =
pregnancy_US =
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legal_AU =
legal_CA =
legal_UK =
legal_US =
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routes_of_administration = Intravenous

Ceftobiprole (brand name Zeftera) is a next generation cephalosporin antibiotic with activity against methicillin-resistant "Staphylococcus aureus", penicillin-resistant "Streptococcus pneumoniae", "Pseudomonas aeruginosa", and Enterococci. [cite journal |author=Yun HC, Ellis MW, Jorgensen JH |title=Activity of ceftobiprole against community-associated methicillin-resistant Staphylococcus aureus isolates recently recovered from US military trainees |journal= |volume= |issue= |pages= |year=2007 |pmid=17911001 |doi=10.1016/j.diagmicrobio.2007.06.023] cite journal|author=Widmer A|title=Ceftobiprole: A new option for treatment of skin and soft-tissue infections due to methicillin-resistant "Staphylococcus aureus"|journal=Clin Infect Dis|year=2008|volume=46|pages=656–8|doi=10.1086/526528] cite journal|author=Noel GJ, Bush K, Bagchi P, Ianus J, Strauss RS|title=A randomized, double-blind trial comparing ceftobiprole medocaril with vancomycin plus ceftazidime plus ceftazidime for the treatment of patients with complicated skin and skin-structure infections|journal=Clin Infect Dis|year=2008|volume=46|pages=647–55|doi=10.1086/526527] It was discovered by Basilea Pharmaceuticacite journal|author=Hebeisen P, Heinze-Krauss I, Angehrn P, "et al."|year=2001|title=In vitro and in vivo properties of Ro63-9141, a novel broad-spectrum cephalosporin with activity against methicillin-resistant staphylococci|journal=Antimicrob Agents Chemother|volume=45|pages=825–36|doi=10.1128/AAC.45.3.825-836.2001] and was developed by Johnson & Johnson Pharmaceutical Research and Development. [ [http://www.basilea.com/template_loader.php?tplpage_id=160 Basilea.com] ] It has been shown to be statistically non-inferior to the combination of vancomycin and ceftazidime for the treatment of skin and soft tissue infections.

It has been described as "fifth generation",cite journal |author=Widmer AF |title=Ceftobiprole: a new option for treatment of skin and soft-tissue infections due to methicillin-resistant Staphylococcus aureus |journal=Clin. Infect. Dis. |volume=46 |issue=5 |pages=656–8 |year=2008 |month=March |pmid=18225983 |doi=10.1086/526528 |url=http://www.journals.uchicago.edu/doi/abs/10.1086/526528?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%3dncbi.nlm.nih.gov] cite journal |author=Kosinski MA, Joseph WS |title=Update on the treatment of diabetic foot infections |journal=Clin Podiatr Med Surg |volume=24 |issue=3 |pages=383–96, vii |year=2007 |month=July |pmid=17613382 |doi=10.1016/j.cpm.2007.03.009 |url=http://journals.elsevierhealth.com/retrieve/pii/S0891-8422(07)00026-2] though acceptance for this terminology is not universal.

Pharmacology

Ceftobiprole inhibits the 2a penicillin-binding protein (pbp) of "Staphylococcus aureus" and the 2x pbp of "Streptococcus pneumoniae" and is active even against methicillin-resistant "Staphylococcus aureus". Ceftobiprole is resistant to staphylococcal β-lactamase.

Dosing

The adult dose of ceftobiprole is 500 mg every eight hours given intravenously. Ceftobiprole cannot be given by mouth. Ceftobiprole is not licensed to be used in children.

Ceftobiprole has been approved for use in Canada, and is under review by regulatory authorities in the United States, the European Union, Australia, Russia, South Africa and Switzerland. [ [http://www.reuters.com/article/companyNewsAndPR/idUSL3062252520080630 Basilea superbug drug approved in Canada] , Reuters News, June 30, 2008]

ynonyms

*RO0639141-000
*BAL9141 [cite journal|author=Jones RN, Deshpande LM, Mutnick AH, Biedenbach DJ|year=2002|title=In vitro evaluation of BAL9141, a novel parenteral cephalosporin active against oxacillin-resistant staphylococci|journal=J Antimicrob Chemother|volume=50|pages=915–932|url=http://jac.oxfordjournals.org/cgi/content/full/50/6/915?ijkey=44287b37747e341869bed979dc42b8250ff5c6ce|doi=10.1093/jac/dkf249]
*Ceftobiprole medocaril

References


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