Ceftibuten

CAS# 97519-39-6

Ceftibuten

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Chemical structure

Ceftibuten

3D structure

Chemical Properties of Ceftibuten

Cas No. 97519-39-6 SDF Download SDF
PubChem ID 5282242 Appearance Powder
Formula C15H14N4O6S2 M.Wt 410.42
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Sch 39720
Solubility Soluble in DMSO
Chemical 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
SMILES C1C=C(N2C(S1)C(C2=O)NC(=O)C(=CCC(=O)O)C3=CSC(=N3)N)C(=O)O
Standard InChIKey UNJFKXSSGBWRBZ-BJCIPQKHSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Ceftibuten Dilution Calculator

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Ceftibuten Molarity Calculator

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Preparing Stock Solutions of Ceftibuten

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4365 mL 12.1826 mL 24.3653 mL 48.7306 mL 60.9132 mL
5 mM 0.4873 mL 2.4365 mL 4.8731 mL 9.7461 mL 12.1826 mL
10 mM 0.2437 mL 1.2183 mL 2.4365 mL 4.8731 mL 6.0913 mL
50 mM 0.0487 mL 0.2437 mL 0.4873 mL 0.9746 mL 1.2183 mL
100 mM 0.0244 mL 0.1218 mL 0.2437 mL 0.4873 mL 0.6091 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Ceftibuten

Ceftibuten(Sch39720) is a third-generation cephalosporin antibiotic. IC50: Target: Antibacterial Ceftibuten displayed high activity against Haemophilus influenzae and Branhamella catarrhalis. There was reduced activity against Streptococcus pneumoniae (MIC90 16 mg/l). The protein binding of Ceftibuten was 77% and the primary target site PBP 3. A high degree of stability to beta-lactamase hydrolysis was observed. [1]

References:
[1]. Wise R, et al. Ceftibuten--in-vitro activity against respiratory pathogens, beta-lactamase stability and mechanism of action. J Antimicrob Chemother, 1990. 26(2): p. 209-213.

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References on Ceftibuten

Ceftibuten-induced filamentation of extended spectrum beta lactamase (ESBL)-producing uropathogenic Escherichia coli alters host cell responses during an in vitro infection.[Pubmed:25433242]

Microb Pathog. 2015 Jan;78:52-62.

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. The presence of Ceftibuten enhanced IL-6, IL-8 and ROS-production from host cells, but only from cells stimulated by the filamentous isolates. The bacterial supernatant and not the filamentous bacteria per se was responsible for the increased release of IL-6, IL-8 and ROS. Increased endotoxin and ATP levels were found in the bacterial supernatants from filamentous isolates. Apyrase decreased IL-6 secretion from A498 cells and polymyxin B abolished the increased ROS-production from PMN cells. PMN were able to inhibit the bacterial growth of some ESBL-isolates in the presence of Ceftibuten. In conclusion, antibiotic-induced filamentation of ESBL-producing UPEC isolates and the associated release of ATP and endotoxins can alter the host cell response in the urinary tract.

Ceftibuten versus trimethoprim-sulfamethoxazole for oral treatment of febrile urinary tract infection in children.[Pubmed:18818954]

Pediatr Nephrol. 2009 Mar;24(3):521-6.

A randomized, open, coordinated multi-center trial compared the bacteriological and clinical efficacy and safety of orally administered Ceftibuten and trimethoprim-sulfamethoxazole (TMP-SMX) in children with febrile urinary tract infection (UTI). Children aged 1 month to 12 years presenting with presumptive first-time febrile UTI were eligible for enrollment. A 2:1 assignment to treatment with Ceftibuten 9 mg/kg once daily (n = 368) or TMP-SMX (3 mg + 15 mg)/kg twice daily (n = 179) for 10 days was performed. Escherichia coli was recovered in 96% of the cases. Among the E. coli isolates, 14% were resistant to TMP-SMX but none to Ceftibuten. In the modified intention-to-treat population, the bacteriological elimination rates at follow-up did not differ significantly between patients treated with Ceftibuten and those treated with TMP-SMX [91 vs. 95%, with a 95% confidence interval (CI) for difference of -9.7 to 1.0]. However, the clinical cure rate was significantly higher among those treated with Ceftibuten (93 vs. 83%, with a 95% CI for difference of 2.4 to 17.0). Adverse events were similar for both regimens and consisted mainly of gastrointestinal disturbances. In conclusion, Ceftibuten is a safe and effective drug for the empirical treatment of febrile UTI in young children.

Inhibitory effect of zinc on the absorption of beta-lactam antibiotic ceftibuten via the peptide transporters in rats.[Pubmed:19122341]

Drug Metab Pharmacokinet. 2008;23(6):464-8.

Zinc is an essential metal ion for the body, and is widely used for nutritional and clinical purposes. Previously, we showed that zinc inhibits the transport of glycylsarcosine via the intestinal peptide transporter PEPT1 in the human intestinal cell line Caco-2. In this study, we examined the effect of zinc on the activity of peptide transporters in rats using the oral beta-lactam antibiotic Ceftibuten as a model drug. The plasma Ceftibuten concentration after intraintestinal administration was decreased in the presence of zinc. The maximum plasma concentration (C(max)) was significantly decreased and the time required to reach C(max) (T(max)) was prolonged by zinc coadministration. The plasma Ceftibuten concentration after iron coadministration or two hours after zinc administration was not affected. The in situ loop technique revealed 50% inhibition of Ceftibuten absorption by zinc. In conclusion, zinc inhibits the transport activity of PEPT1 in vivo as well in vitro.

Ceftibuten-containing agar plate for detecting group B streptococci with reduced penicillin susceptibility (PRGBS).[Pubmed:25959629]

Diagn Microbiol Infect Dis. 2015 Aug;82(4):269-73.

Penicillins remain first-line agents for treatment of group B Streptococcus (Streptococcus agalactiae; GBS) infections; however, several reports have confirmed the existence of GBS with reduced penicillin susceptibility (PRGBS). Because no selective agar plates for detection of PRGBS are available to date, in this investigation, we developed the selective agar plate for detection of PRGBS. We used 19 genetically well-confirmed PRGBS isolates and 38 penicillin-susceptible GBS isolates identified in Japan. For preparation of trial PRGBS-selective agar plates, we added 1 of antimicrobial agents (among oxacillin, ceftizoxime, and Ceftibuten) to a well-established GBS-selective agar plate. Among 12 trial PRGBS-selective agar plates, Muller-Hinton agar containing 128 mug/mL Ceftibuten with 5% sheep blood, 8 mug/mL gentamicin, and 12 mug/mL nalidixic acid was the most appropriate selective agar for PRGBS, showing 100% sensitivity and 81.6% specificity. In cases of potential nosocomial spread of PRGBS, the selective agar plate could be useful and reliable.

Description

Ceftibuten(Sch39720) is a third-generation cephalosporin antibiotic.

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