cefoxitin   Click here for help

GtoPdb Ligand ID: 10937

Synonyms: Cenomycin® | CFX | Mefoxin® | MK-306 | MK306
Approved drug PDB Ligand
cefoxitin is an approved drug (FDA (1978))
Compound class: Synthetic organic
Comment: Cefoxitin is a parenteral, second-generation cephamycin, β-lactam antibacterial. The 7-alpha-methoxy functional group within the structure makes cefoxitin highly resistant to hydrolysis by some β-lactamases. Methicillin-resistant Staphylococcus aureus has acquired resistance to cefoxitin, via expression of the gene for penicillin binding protein 2a (PBP2a). Cefoxitin is active against a broad range of Gram-negative and Gram-positive bacteria, including anaerobes. It is inactive against most strains of Pseudomonas aeruginosa and many strains of Enterobacter cloacae.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 201.8
Molecular weight 427.05
XLogP -1.45
No. Lipinski's rules broken 0
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Canonical SMILES CO[C@@]1(NC(=O)Cc2cccs2)C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)N
Isomeric SMILES CO[C@@]1(NC(=O)Cc2cccs2)C(=O)N2[C@@H]1SCC(=C2C(=O)O)COC(=O)N
InChI InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1
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Summary of Clinical Use Click here for help
Cefoxitin is indicated for infections cuased by susceptible bacteria, including Staphylococcal skin infections, urinary tract infections, bronchitis, tonsillitis, ear infections, bacterial pneumonia, sepsis, bone and joint infections, abdominal infections and abscesses and gonorrhea.
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