• Ceftibuten packaged and labeled.

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SKU: C069

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Description

Ceftibuten is a third generation cephalosporin antibiotic.  It has exceptional beta-lactamase stability and is resistant to inactivation by most B-lactamases made by common Gram-negative and Gram-positive bacteria.  Ceftibuten can be used to study drug resistance and transport pathways.  Ceftibuten is freely soluble in aqueous solution (70.5 mg/mL) and DMSO.

    CAS Number

    97519-39-6

    Molecular Formula

    C15H14N4O6S2

    Molecular Weight

    410.42 g/mol

    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.

    Storage Conditions

    -20°C

    Tariff Code

    2941.90.5000

    Spectrum

    Ceftibuten is a broad spectrum antibiotic targeting a wide variety of Gram-positive and Gram-negative bacteria.

Applications

    Eukaryotic Cell Culture Applications

    Ceftibuten uptake in human intestinal epithelial cells (Caco‐2) cells growing on transwells was studied, and authors found that uptake involves multiple transport pathways. Since cells are polarized, with an apical end and a basolateral end, the apical transport system was found to be different. Apical uptake is mediated by an energy-dependent carrier and energy-independent facilitated diffusion (Menon and Barr 2002).

    Microbiology Applications

    Ceftibuten 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:

    • Haemophilus influenzae 0.015 µg/mL – 1 µg/mL
    • Escherichia coli 0.015 µg/mL - 8 µg/mL
    • For a complete list of ceftibuten MIC values, click here.

Specifications

    Form

    Powder

    Appearance

    White to light yellow crystalline powder

    Source

    Synthetic

    Water Content (Karl Fischer)

    8.0-13.0%

    Optical Rotation

    +135° - +155°

    Assay

    90.0-102.0%

    Residue On Ignition

    ≤0.1%

    Heavy Metals

    ≤10 ppm

    Impurities

    Single Impurity: ≤1.0%
    Total Impurities: ≤2.0%

References

    References

    Debbia EA, Schito CG and Pesce A (1991) Antibacterial Activity of Ceftibuten, a New Oral Third Generation Cephalosporin. J. Chemother 3(4): 209-225

    Georgopapadakou, NH (1992) Mechanisms of action of cephalosporin 3'-quinolone esters, carbamates, and tertiary amines in Escherichia coli." Antimicrob. Agents Chemother. 37(3): 59-65.

    Jones RN and Barry AL (1988) Antimicrobial activity, spectrum, and recommendations for disk diffusion susceptibility testing of ceftibuten (7432-S; SCH 39720), a new orally administered cephalosporin. Antimicrob. Agents and Chemother. 32 (10) 1576-1582; 

    Jones RN (1995) A review of antimicrobial activity, spectrum and other microbiologic features. Pediatr Infect Dis J. 14(7):S77-83 PMID 7567314

    Menon RM and Barr WH (2002) Transporters involved in apical and basolateral uptake of ceftibuten into Caco-2 cells. Biopharmaceutics and Drug Disposition. 23(8):317-326

    Owens RD, Nightingale CH and Nicolau DP (1997) Ceftibuten: An overview. Pharmacother. 17(4):707-720 PMID 9250548

    Perilli M et al (2007) In vitro selection and characterization of mutants in TEM-1-producing Escherichia coli by ceftazidime and ceftibuten. J Chemother 19(2):123-126 PMID 17434819

    Wise R, Andrews JM, Ashby JP and Thornber D (1990) In-vitro activity against respiratory pathogens, β-lactamase stability and mechanism of action, J. Antimicrob Chemother. 26 (2): 209–213 PMID 2120175

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