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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
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)
ChEMBL Ligand CHEMBL996
DrugBank Ligand DB01331
DrugCentral Ligand 550
GtoPdb PubChem SID 405560378
PubChem CID 441199
RCSB PDB Ligand CFX
Search Google for chemical match using the InChIKey WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
Search Google for chemicals with the same backbone WZOZEZRFJCJXNZ
Search PubMed clinical trials cefoxitin
Search PubMed titles cefoxitin
Search PubMed titles/abstracts cefoxitin
UniChem Compound Search for chemical match using the InChIKey WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
UniChem Connectivity Search for chemical match using the InChIKey WZOZEZRFJCJXNZ-ZBFHGGJFSA-N