ceftobiprole   Click here for help

GtoPdb Ligand ID: 10787

Synonyms: BAL-9141 | BAL9141 | BAL9141-000 | BAL9141000 | Ro-63-9141 | Ro-639141 | Zeftera® | Zevtera®
Approved drug
ceftobiprole is an approved drug (UK (2013), FDA (2024))
Compound class: Synthetic organic
Comment: Ceftobiprole is a clinical stage, broad-spectrum, fifth-generation, pyrrolidinone cephalosporin antibacterial [3]. It was developed as a treatment for hospital-acquired pneumonia (HAP) and community-acquired pneumonia (CAP), in particular those infections caused by methicillin-resistant Staphylococcus aureus (MRSA). In clinical trials ceftobiprole is administered by intravenous infusion as the water-soluble prodrug ceftobiprole medocaril (BAL5788; PubChem CID 135413544).

ceftobiprole is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 12
Hydrogen bond donors 5
Rotatable bonds 7
Topological polar surface area 256.98
Molecular weight 534.11
XLogP -3.85
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES O/N=C(/c1nsc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)/C=C/1\CCN(C1=O)[C@H]1CNCC1
Isomeric SMILES O/N=C(/c1nsc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)/C=C/1\CCN(C1=O)[C@H]1CNCC1
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
InChI Key VOAZJEPQLGBXGO-SDAWRPRTSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Ceftobiprole was advanced to Phase 3 clinical evaluation. Marketing authorisation to use ceftobiprole to treat complicated skin and soft-tissue infections was refused by the EMA in 2010 [2], but approval has been granted in individual EU countries (including the UK) as a treatment for hospital-acquired bacterial pneumonia and community-acquired bacterial pneumonia. The FDA approved ceftobiprole medocaril sodium for the treatment of Staphylococcus aureus bloodstream infections (bacteremia), acute bacterial skin and skin structure infections or community-acquired bacterial pneumonia in April 2024.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT00210964 Ceftobiprole in Hospital Acquired Pneumonia Phase 3 Interventional Basilea Pharmaceutica 1
NCT00229008 Ceftobiprole in Hospital Acquired Pneumonia Phase 3 Interventional Basilea Pharmaceutica 1
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)