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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1978))
IUPAC Name Click here for help
(6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
3397 cefoxitin
Synonyms Click here for help
Cenomycin® | CFX | Mefoxin® | MK-306 | MK306
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefoxitin
Reactome Drug Reactome logo R-ALL-9695400
Reactome Reaction Reactome logo R-HSA-9695415
Other databases
CAS Registry No. 35607-66-0 (source: WHO INN record)
DrugBank Ligand DB01331
DrugCentral Ligand 550
GtoPdb PubChem SID 405560378
PubChem CID 441199
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