Ceftobiprole

Ceftobiprole

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Intravenous
ATC code	J01DI01 (WHO)
Legal status
Legal status	Marketed in the UK, France, Italy, Germany, Austria, Switzerland
Identifiers
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 N
PubChem CID	6918430
ChemSpider	23350302 N
UNII	5T97333YZK
KEGG	D08885 Y
ChEMBL	CHEMBL520642 N
ECHA InfoCard	100.129.666
Chemical and physical data
Formula	C20H22N8O6S2
Molar mass	534.568 g/mol
3D model (Jmol)	Interactive image
SMILES C1CNC[C@@H]1N2CC/C(=C\C3=C(N4[C@@H]([C@@H](C4=O)NC(=O)/C(=N\O)/c5nc(sn5)N)SC3)C(=O)O)/C2=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/h5,10,12,18,22,34H,1-4,6-7H2,(H,23,29)(H,32,33)(H2,21,24,26)/b8-5+,25-11-/t10-,12-,18-/m1/s1 N Key:VOAZJEPQLGBXGO-SDAWRPRTSA-N N
NY (what is this?)

Ceftobiprole (Zevtera/Mabelio) is a new 5th-generationcephalosporine for the treatment of hospital-acquired pneumonia (HAP, excluding ventilator-associated pneumonia, VAP) and community-acquired pneumonia (CAP). It is marked by Basilea Pharmaceutica in the United Kingdom, Germany, Switzerland and Austria under the trade name Zevtera, in France and Italy under the trade name Mabelio. Like other cephalosporins, ceftobiprole exerts its antibacterial activity by binding to important penicillin-binding proteins and inhibiting their transpeptidase activity which is essential for the synthesis of bacterial cell walls. Ceftobiprole has high affinity for PBP2a of methicillin-resistant Staphylococcus aureus (MRSA) strains and retains its activity against strains that express divergent mecA gene homologues (mecC or mecALGA251). Ceftobiprole also binds to PBP2b in (penicillin-intermediate), to PBP2x in S. pneumoniae (penicillin resistant), and to PBP5 in Enterococcus faecalis.

Ceftobiprole has shown in vitro antimicrobial activity against a broad range of Gram-positive and Gram-negative pathogens. Among the Gram-positive pathogens, ceftobiprole has demonstrated good in vitro activity against methicillin-resistant Staphylococcus aureus (MRSA), methicillin-susceptible Staphylococcus aureus (MSSA) and coagulase-negative staphylococci, as well as against MRSA strains with reduced susceptibility to linezolid, daptomycin or vancomycin. Ceftobiprole has also displayed potent activity against Streptococcus pneumoniae (including penicillin-sensitive, penicillin-resistant and ceftriaxone-resistant strains) and Enterococcus faecalis, but not against Enterococcus faecium. For Gram-negative pathogens, ceftobiprole has shown good in vitro activity against Haemophilus influenzae (including both ampicillin-susceptible and ampicillin-non-susceptible isolates), Pseudomonas aeruginosa and strains of Escherichia coli, Klebsiella pneumoniae and Proteus mirabilis not producing extended-spectrum β-lactamase (ESBL). Like all other cephalosporines, ceftobiprole was inactive against ESBL producing strains.