Compound ID | 91

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Ceftobiprole (active moiety of ceftobiprole medocaril)

Synonym(s): Zevtera  |  Ceftobiprol  |  Ceftobiprolum  |  BAL9141-000  |  Ceftobiprole

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor. Binds penicillin-binding proteins, inhibits peptidoglycan cross-linking. High affinity for MRSA PBP2a and pneumococcal PBP2x.
Target Pathogen: MRSA, MSSA, Streptococcus pneumoniae, β-haemolytic streptococci, Enterobacterales, and other susceptible Gram-negative pathogens.
Propensity to select resistant mutants: Low; resistance can arise through PBP alterations, β-lactamase production, and permeability changes, but clinically significant resistance remains uncommon.
Description: A cephalosporin
Institute where first reported: Basilea Pharmaceutica, Switzerland
Year first mentioned: 1999
Highest development stage: Approved by FDA in 2024
Development status: Approved
Chemical structure(s):
Click here for structure editor
Molecular weight: 534.57
Iso. SMILES: C1CNC[C@@H]1N2CC/C(=C\C3=C(N4[C@@H]([C@@H](C4=O)NC(=O)/C(=N\O)/C5=NSC(=N5)N)SC3)C(=O)O)/C2=O
InChI Key: VOAZJEPQLGBXGO-SDAWRPRTSA-N
Can. SMILES: C1CNC[C@@H]1N2CC/C(=C\C3=C(C(=O)O)N4C(=O)[C@H]([C@H]4SC3)NC(=O)/C(=N\O)/C5=NSC(=N5)N)/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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/135413542
Guide to Pharmacology: ceftobiprole
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC126986/
  • https://www.tandfonline.com/doi/pdf/10.1080/14787210.2019.1667229
  • https://www.basilea.com/news/news/basilea-announces-positive-results-of-phase-3-target-study-with-antibiotic-ceftobiprole-in-the-treatment-of-acute-bacterial-skin-and-skin-structure-infections-absssi?type=1546938654
    • Patents:
  • WO1999065920A1
  • WO2010050468A1
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