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Ceftobiprole

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Intravenous
ATC code	J01DI01 (WHO)
Identifiers
IUPAC name (6R,7R)-7-amino]-8-oxo-3--3-pyrrolidinylidene]methyl]-5-thia-1- azabicyclooct-2-ene-2-carboxylic acid
PubChem CID	6918430
ChemSpider	21106277
UNII	5T97333YZK
KEGG	D08885
CompTox Dashboard (EPA)	DTXSID40870229
ECHA InfoCard	100.129.666
Chemical and physical data
Formula	C20H22N8O6S2
Molar mass	534.568 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C3N1/C(=C(\CS13NC(=O)C(\N=O)=C2/NSC(\N)=N2)/C=C4\CCN(C4=O)5CCNC5)C(O)=O
InChI InChI=1S/C20H22N8O6S2/c21-20-24-14(26-36-20)11(25-34)15(29)23-12-17(31)28-13(19(32)33)9(7-35-18(12)28)5-8-2-4-27(16(8)30)10-1-3-22-6-10/h5,10,12,18,22,26H,1-4,6-7H2,(H2,21,24)(H,23,29)(H,32,33)/b8-5+,14-11+/t10-,12-,18-/m1/s1 Key:LXLDMYXULSBRCX-KOGKARRDSA-N
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Ceftobiprole (Zeftera/Zevtera) is a 4th generation cephalosporin antibiotic with activity against methicillin-resistant Staphylococcus aureus, penicillin-resistant Streptococcus pneumoniae, Pseudomonas aeruginosa, and Enterococci. It was discovered by Basilea Pharmaceutica and was developed by Johnson & Johnson Pharmaceutical Research and Development. 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 a "fifth generation" cephalosporin, though acceptance for this terminology is not universal.

Pharmacology

Ceftobiprole inhibits the 2a penicillin-binding protein (pbp) of Methicillin-resistant Staphylococcus aureus and the 2x pbp of Streptococcus pneumoniae as well as the classic PBP-2 of MSSA. Ceftobiprole is resistant to staphylococcal β-lactamase.

Dosing

Ceftobiprole cannot be given by mouth and so is given intravenously. It is not FDA approved to be used in children.

Ceftobiprole has been approved for use in Canada and Switzerland, and is under review by regulatory authorities in the United States, the European Union, Australia, Russia and South Africa. In November 2008 the US FDA declined to approve Ceftobiprole citing data integrity concerns with two of the supporting studies, and prompting Basilea to sue Johnson & Johnson for breach of license agreement on February 2009.

Synonyms

• RO0639141-000
• BAL9141
• Ceftobiprole medocaril

References

1. WHO International Working Group for Drug Statistics Methodology (August 27, 2008). "ATC/DDD Classification (FINAL): New ATC 5th level codes". WHO Collaborating Centre for Drug Statistics Methodology. Retrieved 2008-09-05.
2. Kollef MH (2009). "New antimicrobial agents for methicillin-resistant Staphylococcus aureus". Crit Care Resusc. 11 (4): 282–6. PMID 20001879. {{cite journal}}: Unknown parameter |month= ignored (help)
3. Yun HC, Ellis MW, Jorgensen JH (2007). "Activity of ceftobiprole against community-associated methicillin-resistant Staphylococcus aureus isolates recently recovered from US military trainees". Diagnostic Microbiology and Infectious Disease. 59 (4): 463. doi:10.1016/j.diagmicrobio.2007.06.023. PMID 17911001.{{cite journal}}: CS1 maint: multiple names: authors list (link)
4. ^ Widmer A (2008). "Ceftobiprole: A new option for treatment of skin and soft-tissue infections due to methicillin-resistant Staphylococcus aureus". Clin Infect Dis. 46 (5): 656–8. doi:10.1086/526528. PMID 18225983.
5. ^ Noel GJ, Bush K, Bagchi P, Ianus J, Strauss RS (2008). "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". Clin Infect Dis. 46 (5): 647–55. doi:10.1086/526527. PMID 18225981.{{cite journal}}: CS1 maint: multiple names: authors list (link)
6. ^ Hebeisen P, Heinze-Krauss I, Angehrn P; et al. (2001). "In vitro and in vivo properties of Ro63-9141, a novel broad-spectrum cephalosporin with activity against methicillin-resistant staphylococci". Antimicrob Agents Chemother. 45 (3): 825–36. doi:10.1128/AAC.45.3.825-836.2001. PMC 90381. PMID 11181368. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
7. Basilea.com
8. Widmer AF (2008). "Ceftobiprole: a new option for treatment of skin and soft-tissue infections due to methicillin-resistant Staphylococcus aureus". Clin. Infect. Dis. 46 (5): 656–8. doi:10.1086/526528. PMID 18225983. {{cite journal}}: Unknown parameter |month= ignored (help)
9. Kosinski MA, Joseph WS (2007). "Update on the treatment of diabetic foot infections". Clin Podiatr Med Surg. 24 (3): 383–96, vii. doi:10.1016/j.cpm.2007.03.009. PMID 17613382. {{cite journal}}: Unknown parameter |month= ignored (help)
10. Basilea superbug drug approved in Canada, Reuters News, June 30, 2008
11. http://www.dancewithshadows.com/pillscribe/ceftobiprole-antibiotic-to-fight-tougher-bacterial-infections-fails-to-win-approval-in-us/
12. "Basilea Pharmaceutica Ltd. announces that the U.S. Food and Drug Administration (FDA) issued to the sponsor, Johnson & Johnson Pharmaceutical Research and Development, L.L.C. (Johnson & Johnson PRD), a Complete Response Letter on ceftobiprole for the treatment of complicated skin and skin structure infections (cSSSI" (Press release). Basilea Pharmaceutica. 2009-07-02. Retrieved February 2, 2010.
13. Jones RN, Deshpande LM, Mutnick AH, Biedenbach DJ (2002). "In vitro evaluation of BAL9141, a novel parenteral cephalosporin active against oxacillin-resistant staphylococci". J Antimicrob Chemother. 50 (6): 915–932. doi:10.1093/jac/dkf249. PMID 12461013.{{cite journal}}: CS1 maint: multiple names: authors list (link)

• Cephalosporin antibiotics
• Thiadiazoles
• Oximes
• Pyrrolidines
• Pyrrolidones