cefatrizine   Click here for help

GtoPdb Ligand ID: 12204

Synonyms: BL-S640
Compound class: Synthetic organic
Comment: Cefatrizine is a semisynthetic first generation cephalosporin belonging to the β-lactam class of antibacterial compounds.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 5
Rotatable bonds 8
Topological polar surface area 225.13
Molecular weight 462.08
XLogP -1.55
No. Lipinski's rules broken 0
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Canonical SMILES O=C([C@@H](c1ccc(cc1)O)N)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1n[nH]nc1
Isomeric SMILES C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c1ccc(cc1)O)N)C(=O)O)CSc1n[nH]nc1
InChI InChI=1S/C18H18N6O5S2/c19-12(8-1-3-10(25)4-2-8)15(26)21-13-16(27)24-14(18(28)29)9(7-31-17(13)24)6-30-11-5-20-23-22-11/h1-5,12-13,17,25H,6-7,19H2,(H,21,26)(H,28,29)(H,20,22,23)/t12-,13-,17-/m1/s1
Bioactivity Comments
Cefatrizine has broad-spectrum activity against both Gram-positive and Gram-negative bacteria, with greater potency against strains of Haemophilus influenzae, Staphylococcus aureus, and Enterobacteriaceae than earlier first generation cephalosporins [1-2]. The compound does not have significant antibacterial activity against Serratia marcescens and Pseudomonas aeruginosa.