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Purity: ≥98%
Ceftibuten dihydrate, a third-generation cephalosporin antibiotic, is the dihydrate form of ceftibuten which is a semisynthetic, beta-lactamase-stable, cephalosporin with antibacterial activity. Ceftibuten inactivates penicillin-binding proteins located on the inner membrane of the bacterial cell wall. This results in the weakening of the bacterial cell wall and causes cell lysis.
| Targets |
β-lactam
Ceftibuten is a broad-spectrum cephalosporin antibiotic. Its primary mechanism of action, like other β-lactams, is inhibition of bacterial cell wall synthesis.[1] |
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| ln Vitro |
Ceftibuten (Sch-39720) exhibits moderate activity against Serratia sp.and Streptococcus pyogenes, but is highly active against Haemophilus influenza, Escherichia coli, Klebsiella sp., and Proteus sp. Ceftibuten only exhibits weak activity against Pseudomonas aeruginosa and obligate anaerobes, and it is comparatively inactive against enterococci and staphylococci. With the exception of Bacteroides fragilis, it remains stable when most β-lactamase-producing organisms are present. Ceftibuten exhibits high potency against Enterobacteriaceae strains (mean MIC for 90% of strains = 0.25 μg/ml); however, it has comparatively lower efficacy against Campylobacter jejuni strains (mean MIC for 90% of strains = 16.0 μg/ml)[1].
Ceftibuten exhibits potent in vitro antimicrobial activity against a wide range of gram-negative bacteria and certain gram-positive organisms. It is highly active against Haemophilus influenzae, Escherichia coli, Klebsiella sp., and Proteus sp. It shows moderate activity against Serratia sp. and Streptococcus pyogenes. Ceftibuten is relatively inactive against enterococci and staphylococci and is only weakly active against Pseudomonas aeruginosa and obligate anaerobes. It is stable in the presence of most β-lactamase-producing organisms except Bacteroides fragilis. [1] |
| ln Vivo |
Ceftibuten is a biologically stable β-lactam antibiotic that has been demonstrated to exhibit distinct stereoselective and proton-gradient dependent transport characteristics in rat intestinal brush-border membrane vesicles. It has also been shown to be transported by the small peptide transport system and to have a relatively high affinity for the carrier[3].
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| Cell Assay |
The antibacterial susceptibility testing was performed using a standardized broth microdilution method. Twofold serial dilutions of Ceftibuten were prepared in cation-supplemented Mueller-Hinton broth (for Enterobacteriaceae) or Mueller-Hinton broth supplemented with lysed horse blood (for C. jejuni). The final inoculum for each bacterial strain was approximately 5 × 10^5 CFU/ml. Microdilution trays were incubated aerobically at 37°C for 18-24 hours (or in a microaerophilic environment for 48 hours for C. jejuni). The MIC was determined as the lowest concentration inhibiting visible growth. For MBC determination, aliquots from wells showing no visible growth were subcultured onto sheep blood agar. The MBC was defined as the lowest concentration resulting in ≥99.9% kill of the initial inoculum. [2]
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| ADME/Pharmacokinetics |
In 49 children, the cefbuprofen suspension (4.5 or 9.0 mg/kg) was rapidly absorbed after a single oral dose, with a time to peak concentration (Tmax) of approximately 140 minutes. The mean apparent elimination half-life (t1/2) was 2.0 ± 0.5 hours. The mean apparent steady-state volume of distribution (Vss/F) was 0.4 ± 0.2 L/kg. The mean apparent total plasma clearance (CL/F) was 2.5 ± 0.9 mL/min/kg. [1] The mean renal clearance (CLR) of cefbuprofen, measured in a subset of 19 subjects, was 1.02 ± 0.5 mL/min/kg. The mean apparent non-renal clearance (CLNR), estimated by subtracting CLR from CL/F, was 1.3 ± 0.6 mL/min/kg, suggesting a significant non-renal clearance pathway in children. In 9 subjects who received a dose of 9.0 mg/kg and had adequate urine collection, the mean dose recovered in urine over 24 hours was 48.3% (range 18.7–73.9%). [1] Pharmacokinetic parameters showed age dependence. The CL/F (3.1 ± 1.1 mL/min/kg) was significantly higher in children aged 0.5 to ≤5 years than in children >10 years (2.0 ± 0.6 mL/min/kg). Patient age was significantly negatively correlated with elimination half-life and CL/F, and estimated creatinine clearance was also significantly negatively correlated with renal clearance and CL/F. [1]
A confirmatory study of 11 infants (6–26 months) given a dose of 9.0 mg/kg confirmed these findings, showing a CL/F of 3.0 ± 0.5 mL/min/kg. [1] |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation
◉ Overview of use during lactation Limited information suggests that cefoperazone concentrations in breast milk are low and are not expected to have adverse effects on breastfed infants. There have been reports of cephalosporins occasionally disrupting the gut microbiota of infants, leading to diarrhea or thrush, but these effects have not been adequately assessed. Cefoperazone is safe for use by breastfeeding women. ◉ Effects on breastfed infants No published information was found as of the revision date. ◉ Effects on breastfeeding and breast milk No published information was found as of the revision date. In this single-dose study involving 60 pediatric subjects (49 in the primary study and 11 in the validation study), cefoperazone was well tolerated. No adverse reactions associated with a single dose of cefoperazone were observed in any of the subjects. No biochemical evidence of renal or hepatic dysfunction was observed after administration. [1] |
| References |
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| Additional Infomation |
Ceftibuten dihydrate is the dihydrate of Ceftibuten. It is an oral antibacterial drug used to treat urinary tract and respiratory tract infections. It contains the Ceftibuten molecule. Ceftibuten dihydrate is the dihydrate form of Ceftibuten, a semi-synthetic, β-lactamase-stable third-generation cephalosporin with antibacterial activity. Ceftibuten binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of bacterial cell walls. PBPs are enzymes involved in the final stages of bacterial cell wall assembly and in remodeling the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linking of peptidoglycan chains, which is essential for the strength and rigidity of bacterial cell walls. This leads to weakened bacterial cell walls and cell lysis. Cephalosporin antibacterial drugs are used to treat a variety of infections, including urinary tract and respiratory tract infections. See also: Ceftibuten (with active ingredient).
Ceftibuten (SCH 39720) is a newly synthesized broad-spectrum oral cephalosporin. Its antibacterial spectrum and dosage form suggest its potential use in the treatment of otitis media, upper respiratory tract infections, lower respiratory tract infections, and urinary tract infections in infants and young children. [1] Absolute bioavailability of oral Ceftibuten in children was not determined in this study. Therefore, parameters such as CL/F and Vss/F are “apparent” values (expressed as /F) because they were not adjusted for absorption. [1] |
| Molecular Formula |
C15H18N4O8S2
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|---|---|
| Molecular Weight |
446.4554
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| Exact Mass |
446.056
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| Elemental Analysis |
C, 40.35; H, 4.06; N, 12.55; O, 28.67; S, 14.36
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| CAS # |
118081-34-8
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| Related CAS # |
Ceftibuten;97519-39-6;Ceftibuten hydrate;1346153-47-6
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| PubChem CID |
5282241
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| Appearance |
Light yellow to yellow solid powder
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| Boiling Point |
966.4ºC at 760mmHg
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| Melting Point |
>180ºC (dec.)
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| Flash Point |
538.3ºC
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| Vapour Pressure |
0mmHg at 25°C
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| LogP |
0.733
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
29
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| Complexity |
755
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| Defined Atom Stereocenter Count |
2
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| SMILES |
S1C([H])([H])C([H])=C(C(=O)O[H])N2C([C@]([H])([C@@]12[H])N([H])C(/C(=C(/[H])\C([H])([H])C(=O)O[H])/C1=C([H])SC(N([H])[H])=N1)=O)=O.O([H])[H].O([H])[H]
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| InChi Key |
SSWTVBYDDFPFAF-ODPSPGRDSA-N
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| InChi Code |
InChI=1S/C15H14N4O6S2.2H2O/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);2*1H2/b6-1+;;
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| 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;dihydrate
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| Synonyms |
Sch 39720 dihydrate; Sch-39720 dihydrate; Sch39720 dihydrate; Ceftibuten Dihydrate; UNII-62F4443RWP; Seftem; ceftibuten.2H2O; Seftem (TN); Cedax (TN); AC1NQZPM; SCHEMBL159144; CHEBI:34618; HY-B0698A; 62F4443RWP; AKOS025149353; AN-6406; HE068843; HE299817; O441; FT-0664440; D02121; A803878; I06-1263
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ~100 mg/mL (~223.98 mM)
DMSO : 90~100 mg/mL (201.58~223.98 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.60 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.60 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (5.60 mM) Solubility in Formulation 4: 2.26 mg/mL (5.06 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2398 mL | 11.1992 mL | 22.3984 mL | |
| 5 mM | 0.4480 mL | 2.2398 mL | 4.4797 mL | |
| 10 mM | 0.2240 mL | 1.1199 mL | 2.2398 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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