• Ceftazidime pentahydrate packaged and labeled.

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SKU: C059

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Description

Ceftazidime Pentahydrate is a broad-spectrum, third-generation, β-lactam cephalosporin that interferes with bacterial cell wall synthesis.  Patented in 1979 by Glaxo Group, Ceftazidime  came into commercial use in 1984.  It is sparingly soluble in aqueous solution.

    CAS Number

    78439-06-2

    Molecular Formula

    C22H22N6O7S2 •5H2O

    Molecular Weight

    636.65

    Mechanism of Action

    Like 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, however, Ceftazidime is stable in the presence of β-lactamases.

    Storage Conditions

    -20°C

    Tariff Code

    2941.90.3000

    Spectrum

    Ceftazidime Pentahydrate is broad-spectrum, targeting both Gram-negative and Gram-positive bacteria, but is most effective for Gram-negative strains including Pseudomonas aeruginosa and Enterobacteriaceae (including β-lactamase positive strains).  It is also used for against Streptococcus pneumoniae, and S. pyogenes.   

Applications

    Application

    Ceftazidime Pentahydrate is used to study the expression of penicillin-binding proteins, since it disrupts the peptidoglycan layer in bacterial cell walls.

    Eukaryotic Cell Culture Applications

    Human bronchial epithelial cells from chronically infected cystic fibrosis airways were cultured and exposed to Ceftazidime in order to analyze the cytotoxicity.  Even at concentrations many times the antimicrobial level, the compound was nontoxic (Randell et al, 2001).

    Ceftazidime present in aqueous solutions generate cefazidime degradation products (CDPs) that inhibit in vitro HIV-1 replication in cell lines (MT-2 cells transformed with HTLV-I virions, CEM-SS, H9/HTLV-IIIB NIH 1983, Molt-4 clone 8, and U937)  and in primary cells (lymphocytes and macrophages from peripheral blood mononuclear cells).  The exact chemical nature of the active component responsible for the anti-HIV activity is currently unknown other than it is a high molecular weight polymer (MW 8000).  The inhibitory action was manifested during the early phase of the HIV-1 lifecycle (Hobi et al, 2001).

    Microbiology Applications

    Ceftazidime pentahydrate is commonly used in clinical in vitromicrobiological 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 1 µg/mL – 64 µg/mL
    • Escherichia coli 0.06 µg/mL – >32 µg/mL
    • For a complete list of Ceftazidime MIC values, click here.

    Media Supplements

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

    PALCAM Agar - PALCAM Selective Supplement

    ChromogenicListeria Agar - Chromogenic Listeria Selective Supplement

    ChromogenicListeria Agar - Chromogenic Listeria Differential Supplement

Specifications

    Form

    Powder

    Appearance

    White or almost white crystalline powder

    Source

    Synthetic

    Impurity Profile

    Impurity A| delta-2-ceftazidime; ?(2RS,6R,7R)-7-[[(2Z)-2-(2-aminothiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetyl]amino]-8-oxo-3-[(1-pyridinio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate||C22H24N6O7S2|548.60|
    Impurity B| (6R,7R)-7-[[(E)-2-(2-aminothiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetyl]amino]-8-oxo-3-[(1-pyridinio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate||C22H22N6O7S2|546.58|
    Impurity C| (6R,7R)-2-carboxy-8-oxo-3-(pyridiniomethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-7-aminium dichloride||C13H13N3O3S|291.33|
    Impurity D| (6R,7R)-7-[[(Z)-2-[[2-(1,1-dimethylethoxy)-1,1-dimethyl-2-oxoethoxy]imino]-2-[2-[(triphenylmethyl)amino]thiazol-4-yl]acetyl]amino]-8-oxo-3-(pyridiniomethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate||||
    Impurity E| (6R,7R)-7-[[(2Z)-2-(2-aminothiazol-4-yl)-2-[[2-(1,1-dimethylethoxy)-1,1-dimethyl-2-oxoethoxy]imino]acetyl]amino]-8-oxo-3-[(1-pyridinio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate||C26H30N6O7S2|602.69|
    Impurity F| Pyridine|110-86-1|C5H5N|79.10|
    Impurity G| 2-[[[(1Z)-1-(2-aminothiazol-4-yl)-2-[(oxoethyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid||C11H14N4O5S|314.32|
    Impurity H| (6R,7R)-7-[[(2Z)-2-(2-aminothiazol-4-yl)-2-[(2-methoxy-1,1-dimethyl-2-oxoethoxy)imino]acetyl]amino]-8-oxo-3-[(1-pyridinio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate||C23H24N6O7S2|560.61| Ceftazidime| Delta-3-IsoMer||C22H22N6O7S25H2O|636.65|

    pH

    3.0-4.0

    Assay

    (On Dried Basis): 95.0-102.0%

    Loss on Drying

    13.0-15.0%

    Residue On Ignition

    ≤0.2%

    Heavy Metals

    ≤20ppm

    Impurities

    Limit of Pyridine: ≤0.12%
    Ceftazidime Polymer: ≤0.3%

References

    References

    Fischer J and Ganellin R (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 495

    Georgopapadakou NH (1992)  Mechanisms of action of cephalosporin 3'-quinolone esters, carbamates, and tertiary amines in Escherichia coli. Antimicrob. Agents. Chemother37(3): 559-565  PMID
    8384817

    Hobi R et al (2001)  Anti-HIV-1 activity in vitro of Ceftazidime degradation products. Antivir. Chem. and Chemother. 12(2):109-118

    Hsu Y et al (2014)  Biodegradable drug-eluting nanofiber-enveloped implants for sustained release of high bactericidal concentrations of vancomycin and ceftazidime: In vitro and in vivo studies.  Int. J. Nanomed.  9:4347-4355

    Randell SH, Walstad DL, Schwab UE, Grubb BR and Yankaskas JR (2001)  Isolation and culture of airway epithelial cells from chronically infected human lungs. In Vitro Cell. Dev. Biol.-Animal 37: 480

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