cefamandole   Click here for help

GtoPdb Ligand ID: 12210

Synonyms: cephamandole
Approved drug PDB Ligand
cefamandole is an approved drug (FDA (1978))
Compound class: Synthetic organic
Comment: Cefamandole is a semisynthetic, second generation cephalosporin belonging to the β-lactam class of antibacterial compounds [1]. It has broad-spectrum activity and is β-lactamase-resistant. It is administered parenterally as the prodrug cefamandole nafate.
Because of its inhibitory activity towards human aldehyde dehydrogenase, cefamandole produces an effect to ethanol similar to that produced by disulfiram (Antabuse®).
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 201.14
Molecular weight 462.51
XLogP 0.2
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O[C@@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)c1ccccc1
Isomeric SMILES Cn1c(nnn1)SCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](c2ccccc2)O)SC1)C(=O)O
InChI InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1
InChI Key OLVCFLKTBJRLHI-AXAPSJFSSA-N
Bioactivity Comments
Cefamandole has broad-spectrum antibacterial activity [1].