ceftizoxime   Click here for help

GtoPdb Ligand ID: 10785

Synonyms: Cefizox® | compound 22 {PMID: 2342058] | Epocelin® | FK-749 | FK749 | FR-13749 | FR13749 | SK&F 88373-Z
Approved drug
ceftizoxime is an approved drug (FDA (1983))
Compound class: Synthetic organic
Comment: Ceftizoxime is a semisynthetic, broad-spectrum, β-lactamase-resistant, parenterally administered third-generation cephalosporin antibiotic with Gram +ve and Gram -ve activity. Unlike other third-generation cephalosporins, ceftizoxime's C-3 side chain has been removed to prevent deactivation by hydrolytic enzymes.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 200.75
Molecular weight 383.04
XLogP -2.27
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CO/N=C(/c1csc(n1)N)\C(=O)N[C@H]1[C@H]2SCC=C(N2C1=O)C(=O)O
Isomeric SMILES CO/N=C(/c1csc(n1)N)\C(=O)N[C@H]1[C@H]2SCC=C(N2C1=O)C(=O)O
InChI InChI=1S/C13H13N5O5S2/c1-23-17-7(5-4-25-13(14)15-5)9(19)16-8-10(20)18-6(12(21)22)2-3-24-11(8)18/h2,4,8,11H,3H2,1H3,(H2,14,15)(H,16,19)(H,21,22)/b17-7-/t8-,11-/m1/s1
InChI Key NNULBSISHYWZJU-LLKWHZGFSA-N
References
1. Blaszczak LC, Brown RF, Cook GK, Hornback WJ, Hoying RC, Indelicato JM, Jordan CL, Katner AS, Kinnick MD, McDonald 3rd JH et al.. (1990)
Comparative reactivity of 1-carba-1-dethiacephalosporins with cephalosporins.
J Med Chem, 33 (6): 1656-62. [PMID:2342058]
2. Cui L, Neoh HM, Shoji M, Hiramatsu K. (2009)
Contribution of vraSR and graSR point mutations to vancomycin resistance in vancomycin-intermediate Staphylococcus aureus.
Antimicrob Agents Chemother, 53 (3): 1231-4. [PMID:19124662]