cefuroxime   Click here for help

GtoPdb Ligand ID: 10900

Synonyms: Ceftin® | CXM | Kefurox® | Zinacef®
Approved drug PDB Ligand
cefuroxime is an approved drug (FDA (1983))
Compound class: Synthetic organic
Comment: Cefuroxime is a semisynthetic, second-generation cephalosporin antibacterial. It has broad-spectrum activity and is β-lactamase-resistant. Oral formulations contain the prodrug cefuroxime axetil.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 199.06
Molecular weight 424.07
XLogP -0.8
No. Lipinski's rules broken 0
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Canonical SMILES CO/N=C(\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)N)/c1ccco1
Isomeric SMILES CO/N=C(\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)N)/c1ccco1
InChI InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1983))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
3902 cefuroxime
Synonyms Click here for help
Ceftin® | CXM | Kefurox® | Zinacef®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefuroxime
Reactome Drug Reactome logo R-ALL-9695388
Reactome Reaction Reactome logo R-HSA-9695415
Other databases
BindingDB Ligand 50422689
CAS Registry No. 55268-75-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL1436
DrugBank Ligand DB01112
DrugCentral Ligand 565
GtoPdb PubChem SID 405560341
PubChem CID 5479529
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UniChem Compound Search for chemical match using the InChIKey JFPVXVDWJQMJEE-IZRZKJBUSA-N
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