• Cefoxitin packaged and labeled.

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SKU: C091

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Description

Cefoxitin is a cephamycin β-lactam second- generation cephalosporin.  Cefoxitin is resistant to β-lactamases.  Cefoxitin is sparingly soluble in aqueous solution. 

We also offer:

  • Cefoxitin sodium (C054)

    CAS Number

    35607-66-0

    Molecular Formula

    C16H17N3O7S2

    Molecular Weight

    427.46 g/mol

    Mechanism of Action

    Like β-lactams, cephamycins interfere with PBP (penicillin binding protein) activity involved in the final phase of peptidoglycan synthesis. PBP’s are enzymes which catalyze a pentaglycine crosslink between alanine and lysine residues providing additional strength to the cell wall. Without a pentaglycine crosslink, the integrity of the cell wall is severely compromised and ultimately leads to cell lysis and death. Resistance to cephamycins is commonly due to cells containing plasmid encoded β-lactamases.

    Storage Conditions

    -20°C

    Tariff Code

    2941.90.5000

    Spectrum

    Cefoxitin is a broad-spectrum antibiotic effective against several Gram-positive and Gram-negative bacteria. Like many cephamycins, Cefoxitin is particularly effective against anaerobic bacteria.

Applications

    Microbiology Applications

    Cefoxitin is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against Gram-positive and Gram-negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options for infected patients. Representative MIC values include:

    • Bacteroides fragilis 1 µg/mL – 8 µg/mL
    • Bacillus cereus 8.6 µg/mL
    • For a complete list of Cefoxitin MIC values, click here.

    Media Supplements

    Cefoxitin can be used as a selective agent in several types of isolation media:

    Clostridium difficile agar - Isolation of Clostridium difficile

Specifications

    Form

    Powder

    Appearance

    white or almost white powder

    Source

    Semi-synthetic

    Impurity Profile

    Impurity A| Decarbamoylcefoxitin;(6R,7S)-3-(hydroxymethyl)-7-methoxy-8-oxo-7-[[(thiophen-2-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid|54333-94-7|C15H16N2O6S2|384.43| Impurity B| delta-3-cefoxitin; (2RS,6R,7S)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[[(thiophen-2-yl)acetyl]amino]-5-thia-1-azabicyclo [4.2.0]oct-3-ene-2-carboxylic acid||C16H17N3O7S2|427.454| Impurity C| cefalotin lactone; (5aR,6R)-6-[[(thiophen-2-yl)acetyl]amino]-5a,6-dihydro-3H,7H-azeto[2,1-b]furo[3,4-d][1,3]thiazine-1,7(4H)-dione||C13H12N2O4S2|324.38| Impurity D| cefoxitin lactone; (5aR,6S)-6-methoxy-6-[[(thiophen-2-yl)acetyl]amino]-5a,6-dihydro-3H,7H-azeto[2,1-b]furo[3,4-d][1,3]thiazine-1,7(4H)-dione||C14H14N2O4S2|338.4| Impurity E| (6R,7S)-3-[(carbamoyloxy)methyl]-7-(methyloxy)-7-[[(2R)-2-(methyloxy)-2-(2-thienyl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid ((R)-methoxy cefoxitin)||C17H19N3O8S2|425.42| Impurity F| (6R,7S)-3-[(carbamoyloxy)methyl]-7-(methyloxy)-7-[[(2S)-2-(methyloxy)-2-(2-thienyl)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid ((S)-methoxy cefoxitin)||C17H19N3O8S2|425.42| Impurity G| (6R,7S)-3-[[[[[(6R,7S)-2-carboxy-7-(methyloxy)-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]oxy]carbamoyloxy]methyl]-7-(methyloxy)-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (cefoxitindimer)|

    Water Content (Karl Fischer)

    ≤5.0%

    pH

    2.5-3.5

    Optical Rotation

    +195° to +208°

    Assay

    ≥98.0% (on dried basis)

    Impurities

    Related Substances:
    Single Impurity: ≤0.4%
    Total Impurities: ≤1.0%

References

    References

    Georgopapadakou NH (1992)  Mechanisms of action of cephalosporin 3'-quinolone esters, carbamates, and tertiary amines in Escherichia coli."  Antimicrob. Agents. Chemother.  37 (3): 559-65

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