SKU: C010  / 
    CAS Number: 62893-20-3

    Cefoperazone sodium

    $57.91 - $198.85

    Cefoperazone sodium is a third generation cephalosporin antibiotic.  It is semi-synthetic, β-lactamase resistant, with broad-spectrum bactericidal activity.  It is used to study drug-protein binding such as penicillin binding proteins.  Cefoperazone A is the principal metabolite.  Cefoperazone sodium is freely soluble in aqueous solution (50 mg/mL).

    Mechanism of ActionLike β-lactams, cephalosporins 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 cephalosporins is commonly due to cells containing plasmid encoded β-lactamases. Cefoperazone however, is largely resistant to β-lactamases produced by resistant cells.
    SpectrumCefoperazone is active against Gram-positive and Gram-negative bacteria (ie Pseudomonas aeruginosa).
    Impurity ProfileImpurity A| (5aR,6R)-6-[[(2R)-2-[[(4-ethyl-2,3-dioxopiperazin-1-yl)-carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-5a,6-dihydro-3H, 7H-azeto[2,1-b]furo[3,4-d][1,3]thiazine-1,7(4H)-dione|73240-08-1|C23H23N5O8S|529.53| Impurity B| (6R,7R)-7-[[(2R)-2-[[(4-ethyl-2,3-dioxopiperazin-1-yl)-carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(4-methyl-5-thioxo-4,5-dihydro-1H-tetrazol-1-yl)methyl]-8-oxo-5-thial-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid|711590-76-4|C25H26N9O8S2|644.67| Impurity C| 1-methyl-1H-tetrazole-5-thiol;|69713-31-1|C2H4N4S|116.145| Impurity D| (6R,7R)-7-amino-8-oxo-3-[(1H-1,2,3-triazol-4-yl-sulphanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (7-TACA)|37539-03-0|C10H11N5O3S2|313.356| Impurity E| 7ACA|957-68-6|C10H12N2O5S|272.28| Impurity F| (6R,7S)-7-[[(2R)-2-[[(4-ethyl-2,3-dioxopiperazine-1-yl)-carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)sulphanyl]methyl]-8-oxo-5-thial-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid|1315481-36-7|C25H26N9O8S2|644.67|
    Microbiology ApplicationsCefoperazone is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against gram negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options for infected patients. Representative MIC values include:

    • Pseudomonas aeruginosa 0.5 µg/mL – 64 µg/mL
    • Haemophilus influenzae 0.06 µg/mL – 2 µg/mL
    • For a complete list of cefoperazone MIC values, click here.

    Media Supplements

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

    Campylobacter Blood-Free Selective Agar - CCDA Selective Supplement

    Campylobacter Agar - Campylobacter Selective Supplement (Karmali)

    Blood Free Campylobacter Agar - CDMN Selective Supplement

    Bolton Broth - Bolton Broth Selective Supplement

    Campylobacter Agar Base - Modified Karmali Selective Supplement

    Bolton Broth - Modified Bolton Broth Selective Supplement

    Molecular FormulaC25H26N9NaO8S2
    ReferencesBrogden RN et al (1981) Cefoperazone: A review of its in vitro antimicrobial activity, pharmacological properties and therapeutic efficacy. Drugs 22:423-460 PMD 6459224

    Georgopapadakou, N. H. Mechanisms of Action of Cephalosporin 3'-quinolone Esters, Carbamates, and Tertiary Amines in Escherichia Coli. Antimicrobial Agents and Chemotherapy.  37(3) 559-565

    Hinkle AM, LeBlanc BM, Bodey GP (1980) In vitro evaluation of cefoperazone. Antimicrobial Agents Chemother. 17(3):423-427 PMID 6448578

    Matsubara N, Minami S, Muraoka T, Saikawa I, Mitsuhashi S (1979) In vitro antibacterial activity of cefoperazone (T-1551), a new semisynthetic cephalosporin. Antimicrob Agents Chemother. 16(6):731-5 PMID 316988