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))
Compound class: Synthetic organic
Comment: Ceftobiprole is a clinical stage, broad-spectrum, fifth-generation, pyrrolidinone cephalosporin antibiotic [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).
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (UK (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 91
Other databases
CAS Registry No. 209467-52-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL520642
GtoPdb PubChem SID 405560228
PubChem CID 135413542
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