A broad-spectrum cephalosporin antibiotic
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Ceftibuten (hydrate)

Item No. 25334

Technical Information
Formal Name
(6R,7R)-7-[[(2Z)-2-(2-amino-4-thiazolyl)-4-carboxy-1-oxo-2-buten-1-yl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, dihydrate
CAS Number
118081-34-8
Synonyms
  • SCH 39720
Molecular Formula
C15H14N4O6S2 • 2H2O
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 2 mg/mlDMSO: 5 mg/mlPBS (pH 7.2): 0.1 mg/ml
λmax
218, 262 nm
SMILES
OC(C1=CCS[C@@]([C@@H]2NC(/C(C3=CSC(N)=N3)=C\CC(O)=O)=O)([H])N1C2=O)=O
InChi Code
InChI=1S/C15H14N4O6S2/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(14(24)25)3-4-26-13(10)19/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25)/b6-1-/t10-,13-/m1/s1
InChi Key
UNJFKXSSGBWRBZ-BJCIPQKHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Ceftibuten is an orally bioavailable broad-spectrum cephalosporin antibiotic that inhibits the growth of B. catarrhalis, H. influenzae, pathogenic Neisseria, Streptococcus, penicillin-susceptible S. pneumoniae, and eleven Enterobacteriaceae strains (MICs = 0.25, ≤0.06, ≤0.06, 0.5-1, 4, and ≤0.06-0.5 μg/ml, respectively).1,2 Ceftibuten is also active against E. coli expressing β-lactamase type I, III, and V and K. oxytoca expressing β-lactamase type IV (MICs = 8, 0.25, 0.5, and ≤0.06 μg/ml, respectively) as well as a panel of eight bacterial stains expressing plasmid-encoded extended spectrum β-lactamases, including E. coli CTX-M and K. pneumoniae SHV-2 (MICs = 1 and 0.25 μg/ml, respectively). In vivo, ceftibuten reduces the number of mice killed within 6 days of a K. pneumoniae, E. coli, S. pneumoniae, or S. aureus infection by 50% when administered subcutaneously at doses of 0.125, 2, 1,024, and >512 mg/kg, respectively.3 Formulations containing ceftibuten have been used in the treatment of bacterial infections including bronchitis, pneumonia, and enteritis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bauernfeind, A. Ceftibuten and bactericidal kinetics. Comparative in vitro activity against Enterobacteriaceae producing extended spectrum β-lactamases. Diagn. Microbiol. Infect. Dis. 14(1), 89-92 (1991).

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

    3. Onyeji, C.O., Nicolau, D.P., Nightingale, C.H., et alOptimal times above MICs of ceftibuten and cefaclor in experimental intra-abdominal infections. Antimicrob. Agents Chemother. 38(5), 1112-1117 (1994).