• Cefoxitin packaged and labeled.

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SKU: C091

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Description

Cefoxitin is a cephamycin β-lactam antibiotic grouped with the second generation cephalosporins.  Like many cephamycins, cefoxitin is resistant to β-lactamases.

TOKU-E offers two forms of cefoxitin: cefoxitin (C091) and cefoxitin sodium (C054). In aqueous solution, cefoxitin is sparingly soluble (0.195 mg/mL) and cefoxitin sodium is freely soluble. Both forms have similar potencies and are suitable for microbiology use; however, cefoxitin sodium is easier to work with in aqueous solution because of its higher solubility.

    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 vitromicrobiological 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, N. H. "Mechanisms of Action of Cephalosporin 3'-quinolone Esters, Carbamates, and Tertiary Amines in Escherichia Coli." American Society for Microbiology 37.3 (1992): 559-65. Antimicrobial Agents and Chemotherapy. Web. 21 Aug. 2012.

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