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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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. UK MHRA (2013)
IUPAC Name Click here for help
(6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-[(E)-[2-oxo-1-[(3R)-pyrrolidin-3-yl]pyrrolidin-3-ylidene]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
8531 ceftobiprole
Synonyms Click here for help
BAL-9141 | BAL9141 | BAL9141-000 | BAL9141000 | Ro-63-9141 | Ro-639141 | Zeftera® | Zevtera®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Ceftobiprole (active moiety of ceftobiprole medocaril)
Other databases
CAS Registry No. 209467-52-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL520642
GtoPdb PubChem SID 405560228
PubChem CID 135413542
Search Google for chemical match using the InChIKey VOAZJEPQLGBXGO-SDAWRPRTSA-N
Search Google for chemicals with the same backbone VOAZJEPQLGBXGO
Search PubMed clinical trials ceftobiprole
Search PubMed titles ceftobiprole
Search PubMed titles/abstracts ceftobiprole
UniChem Compound Search for chemical match using the InChIKey VOAZJEPQLGBXGO-SDAWRPRTSA-N
UniChem Connectivity Search for chemical match using the InChIKey VOAZJEPQLGBXGO-SDAWRPRTSA-N

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MedChemExpress
Ceftobiprole (links to external site)
Cat. No. HY-112579