Ceftibuten
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| Category | Antibiotics |
| Catalog number | BBF-00747 |
| CAS | 97519-39-6 |
| Molecular Weight | 410.42 |
| Molecular Formula | C15H14N4O6S2 |
| Purity | >98% |
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Description
It is produced by the strain of Semisynthetic third generation oral cephalosporin. The activity of Ceftibuten against enterobacteriaceae which can produce broad-spectrum β-lactamase was superior to cefotaxime and amtriannan, the activity of Ceftibuten against gram-negative bacteria was stronger than cefacolol, but the activity against gram-positive bacteria was poor, and the activity against Streptococcus pneumoniae was only 1/8 of Ceftibuten. It is used to treat acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsilitis.
Specification
| Related CAS | 118081-34-8 (Dihydrate) |
| Synonyms | Ceftibuteno; Cedax; Ceftibutenum; Ceftibutene; cis-ceftibuten; Cephem; Sch39720; Sch 39720; Sch-39720; (+)-(6R,7R)-7-((Z)-2-(2-Amino-4-thiazolyl)-4-carboxycrotonamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid |
| Storage | 2-8 °C |
| IUPAC Name | (6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Canonical SMILES | C1C=C(N2C(S1)C(C2=O)NC(=O)C(=CCC(=O)O)C3=CSC(=N3)N)C(=O)O |
| InChI | 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 |
| Source | Synthetic |
Properties
| Appearance | White to light yellow crystalline powder |
| Application | Anti-Bacterial Agents |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Boiling Point | 966.0 °C |
| Density | 1.75±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Aqueous solutions, DMSO |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Ceftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis. |
Reference Reading
1.High isolation rate of MDR group B streptococci with reduced penicillin susceptibility in Japan.
Seki T1, Kimura K2, Reid ME1, Miyazaki A1, Banno H1, Jin W1, Wachino J1, Yamada K1, Arakawa Y1. J Antimicrob Chemother. 2015 Oct;70(10):2725-8. doi: 10.1093/jac/dkv203. Epub 2015 Jul 13.
OBJECTIVES: In Japan, the isolation rate of group B Streptococcus (GBS) with reduced penicillin susceptibility (PRGBS) was 2.3% between 2005 and 2006. However, no data on this have been available since then; moreover, the isolation rate of MDR-PRGBS has never been reported. The aim of this study was to obtain recent data on the PRGBS isolation rate and to investigate, for the first time, the isolation rate of MDR-PRGBS.
2.Comparative in vitro activity of oral antimicrobial agents against Enterobacteriaceae from patients with community-acquired urinary tract infections in three European countries.
Kresken M1, Körber-Irrgang B2, Biedenbach DJ3, Batista N4, Besard V5, Cantón R6, García-Castillo M6, Kalka-Moll W7, Pascual A4, Schwarz R7, Van Meensel B8, Wisplinghoff H9, Seifert H10. Clin Microbiol Infect. 2016 Jan;22(1):63.e1-5. doi: 10.1016/j.cmi.2015.08.019. Epub 2015 Aug 29.
Enterobacteriaceae causing community-acquired urinary tract infections were examined in selected outpatient clinics and hospitals in Belgium, Germany and Spain using EUCAST breakpoints for susceptibility. A total of 1190 isolates were collected. Escherichia coli isolates were resistant to amoxicillin-clavulanic acid (28.1%), ciprofloxacin (23.4%) and trimethoprim-sulfamethoxazole (21.4%) compared with fosfomycin and nitrofurantoin (each, <1.5%). Ceftibuten (MIC50/90 0.25/0.5 mg/L) and ceftriaxone activity (MIC50/90 ≤0.25 mg/L) was comparable. Ceftibuten (MIC90 ≤0.25 mg/L) was also active against Proteus mirabilis and Klebsiella spp. Extended-spectrum β-lactamase phenotypes were 7.1% for E. coli, 5.6% for Klebsiella pneumoniae and 0.4% for P. mirabilis. Resistance was common among men and elderly women.
3.Fosfomycin trometamol: a review of its use as a single-dose oral treatment for patients with acute lower urinary tract infections and pregnant women with asymptomatic bacteriuria.
Keating GM1. Drugs. 2013 Nov;73(17):1951-66. doi: 10.1007/s40265-013-0143-y.
Fosfomycin trometamol (fosfomycin tromethamine) [Monuril(®), Monurol(®), Monural(®)] is approved in numerous countries worldwide, mainly for the treatment of uncomplicated urinary tract infections (UTIs). Fosfomycin has good in vitro activity against common uropathogens, such as Escherichia coli (including extended-spectrum β-lactamase-producing E. coli), Proteus mirabilis, Klebsiella pneumoniae and Staphylococcus saprophyticus, and the susceptibility of uropathogens to fosfomycin has remained relatively stable over time. A single oral dose of fosfomycin trometamol 3 g (the approved dosage) achieves high concentrations in urine. Results of recent randomized trials indicate that single-dose fosfomycin trometamol had similar clinical and/or bacteriological efficacy to 3- to 7-day regimens of ciprofloxacin, norfloxacin, cotrimoxazole or nitrofurantoin in women with uncomplicated lower UTIs. In addition, single-dose fosfomycin trometamol had similar bacteriological efficacy to a 5-day course of cefuroxime axetil or a 7-day course of amoxicillin/clavulanic acid in pregnant women with asymptomatic bacteriuria, and similar clinical and/or bacteriological efficacy to a 5-day course of cefuroxime axetil or amoxicillin/clavulanic acid or a 3-day course of ceftibuten in pregnant women with a lower UTI.
4.Ceftibuten-induced filamentation of extended spectrum beta lactamase (ESBL)-producing uropathogenic Escherichia coli alters host cell responses during an in vitro infection.
Demirel I1, Kruse R2, Önnberg A2, Persson K2. Microb Pathog. 2015 Jan;78:52-62. doi: 10.1016/j.micpath.2014.11.015. Epub 2014 Nov 27.
Inadequate and delayed antibiotic treatment of extended spectrum beta-lactamase (ESBL)-producing isolates have been associated with increased mortality of affected patients. The purpose of this study was to compare the host response of human renal epithelial cells and polymorphonuclear leucocyte (PMN) cells when infected by ESBL-producing uropathogenic Escherichia coli (UPEC) isolates in the presence or absence of ineffective antibiotics. The renal epithelial cell line A498 and PMN cells were stimulated with ESBL-producing UPEC isolates in the presence or absence of three different antibiotics (trimetoprim, ceftibuten and ciprofloxacin). Host cell responses were evaluated as release of cytokines (IL-6, IL-8), reactive oxygen species (ROS), ATP and endotoxins. Bacterial morphology and PMN phagocytosis were evaluated by microscopy. In the presence of ceftibuten, 2 out of 3 examined ESBL-isolates changed their morphology into a filamentous form.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C15H14N4O6S2
Molecular Weight (Monoisotopic Mass): 410.0355 Da
Molecular Weight (Avergae Mass): 410.425 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C15H14N4O6S2
Molecular Weight (Monoisotopic Mass): 410.0355 Da
Molecular Weight (Avergae Mass): 410.425 Da
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C15H14N4O6S2
Molecular Weight (Monoisotopic Mass): 410.0355 Da
Molecular Weight (Avergae Mass): 410.425 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C15H14N4O6S2
Molecular Weight (Monoisotopic Mass): 410.0355 Da
Molecular Weight (Avergae Mass): 410.425 Da
13C NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
