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| 1mg |
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| Other Sizes |
| Targets |
Penicillin-binding proteins (PBPs). Cefteram, like other beta-lactam antibiotics, binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the peptidoglycan layer and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains, leading to weakening of the bacterial cell wall and causing osmotic lysis.
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| ln Vitro |
Cefteram is a third-generation cephalosporin antibiotic with broad-spectrum antibacterial activity. It is effective against both Gram-positive and Gram-negative bacteria, including pathogens responsible for respiratory tract infections (e.g., Streptococcus pneumoniae, Haemophilus influenzae), urinary tract infections (e.g., E. coli, Klebsiella pneumoniae), and skin infections. It has good activity against beta-lactamase-producing strains. While specific MIC values vary, it is generally active at concentrations of ≤1 ug/mL against many common pathogens.
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| ln Vivo |
Cefteram is effective in treating bacterial infections in vivo. It has been used in clinical settings for respiratory tract infections, urinary tract infections, and skin infections. In research settings, it is used as a positive control in animal models of bacterial infection. It has good oral bioavailability in animal models, making it suitable for pharmacokinetic and efficacy studies. It has a maximum clinical trial phase of II and has one investigational indication.
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| Enzyme Assay |
Cefteram binds to PBPs. For cell-free binding assays, purified penicillin-binding proteins (PBPs) from bacterial membranes are isolated. Bacterial cells (e.g., E. coli or S. aureus) are lysed, and membrane fractions are prepared by ultracentrifugation. The membrane fraction (50-100 ug protein) is incubated with various concentrations of Cefteram (0.1 nM-100 uM) in 50 mM potassium phosphate buffer (pH 7.0) at 30degC for 10-30 minutes. Then, a radiolabeled penicillin (e.g., 14C-benzylpenicillin) is added and incubated for another 10 minutes. The reaction is stopped with SDS-PAGE sample buffer. Samples are separated by SDS-PAGE, and the gel is exposed to a phosphorimager screen. The intensity of the PBP bands is quantified. The IC50 for each PBP is determined as the concentration of Cefteram required to inhibit 50% of radiolabeled penicillin binding. Alternatively, a fluorescent penicillin analog can be used for detection. For susceptibility testing, standard broth microdilution methods are used.
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| Cell Assay |
For antibacterial assays, clinical isolates are cultured in appropriate media. Minimum inhibitory concentrations (MICs) are determined using the broth microdilution method according to CLSI guidelines. Bacteria are suspended in cation-adjusted Mueller-Hinton broth to a density of 5×10⁵ CFU/mL. Cefteram is serially diluted (0.001-100 ug/mL) in 96-well plates. The bacterial suspension is added, and plates are incubated at 35degC for 18-24 hours. The MIC is the lowest concentration that inhibits visible growth. For time-kill assays, bacterial cultures are treated with Cefteram at concentrations of 1×, 2×, and 4× MIC, and aliquots are plated at 0, 2, 4, 6, 12, and 24 hours to determine viable counts. The antibacterial spectrum includes activity against methicillin-susceptible S. aureus (MSSA), S. pneumoniae, H. influenzae, M. catarrhalis, E. coli, K. pneumoniae, and P. mirabilis.
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| Animal Protocol |
In a murine model of systemic infection, female ICR mice (6-8 weeks old, 18-22 g) are challenged intraperitoneally with a lethal dose of bacteria (e.g., 10⁶ CFU/mouse of S. aureus or E. coli) suspended in 5% mucin. Cefteram is administered subcutaneously or orally at doses of 1-100 mg/kg, typically given 1 hour post-infection and once daily thereafter for 3-5 days. Survival is monitored for 7 days. ED50 values are calculated by probit analysis. In a murine thigh infection model, neutropenic mice (rendered neutropenic by cyclophosphamide) are infected intramuscularly with 10⁵-10⁶ CFU of bacteria. Cefteram is administered subcutaneously at various doses (0.1-100 mg/kg). After 24 hours, mice are euthanized, and thigh muscles are homogenized for bacterial CFU enumeration. Efficacy is expressed as the log10 reduction in CFU/g compared to untreated controls.
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| ADME/Pharmacokinetics |
Cefteram is administered intravenously or orally. In preclinical studies (rats), Cefteram has moderate oral bioavailability (approximately 50-70%). The compound is well distributed to tissues, with higher concentrations in kidney, lung, and liver. The elimination half-life is approximately 1-2 hours. The pivaloyloxymethyl ester prodrug (Cefteram pivoxil) is used clinically to improve oral bioavailability. Cefteram is primarily excreted unchanged in urine. In humans, Cefteram pivoxil is approved for use in Japan.
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| Toxicity/Toxicokinetics |
Cefteram is generally well tolerated in clinical use. Common side effects include gastrointestinal disturbances (diarrhea, nausea, abdominal pain). Allergic reactions (rash, urticaria) may occur in penicillin-allergic patients. As with other cephalosporins, it may cause transient elevations in liver enzymes and, rarely, hematological effects (eosinophilia, neutropenia). Pseudomembranous colitis (C. difficile-associated diarrhea) has been reported. No significant drug-drug interactions have been reported.
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| References |
[1]. Hohl P, et al. In vitro activity of cefteram against predominantly enteropathogenic and glucose nonfermentative gram-negatives. Chemotherapy. 1989;35(4):242-5.
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| Additional Infomation |
Cefteram is a semi-synthetic, broad-spectrum, third-generation cephalosporin with antibacterial activity. Cefteram binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the final stages of bacterial cell wall assembly and in remodeling the cell wall during bacterial growth and division. Inactivation of PBPs interferes with the cross-linking of peptidoglycan chains, which is crucial for maintaining the strength and rigidity of the bacterial cell wall. This leads to weakening of the bacterial cell wall, ultimately resulting in cell lysis.
See also: Cefteram (Note moved to). Cefteram is a third-generation cephalosporin antibiotic. It is formulated as Cefteram pivoxil for oral administration (prodrug). It was first introduced in Japan in 1991. It is used in research for antibacterial studies and as a reference compound in antimicrobial susceptibility testing. It is not approved for use in the US or Europe but is approved in some Asian countries. For research use only. Molecular formula: C16H17N9O5S2. IUPAC name: (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(5-methyltetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. |
| Molecular Formula |
C16H17N9O5S2
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|---|---|
| Molecular Weight |
479.49
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| Exact Mass |
479.079
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| Elemental Analysis |
C, 40.08; H, 3.57; N, 26.29; O, 16.68; S, 13.37
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| CAS # |
82547-58-8
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| PubChem CID |
5464257
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| Appearance |
Solid powder
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| Density |
1.95 g/cm3
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| Melting Point |
>175ºC (dec.)
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| Index of Refraction |
1.901
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| LogP |
-0.9
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
13
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
32
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| Complexity |
871
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| Defined Atom Stereocenter Count |
2
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| SMILES |
C(C1=C(CN2N=NC(C)=N2)CS[C@@H]2[C@@H](C(N12)=O)NC(=O)/C(/C1=CSC(N)=N1)=N\OC)(=O)O
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| InChi Key |
XSPUSVIQHBDITA-RKYNPMAHSA-N
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| InChi Code |
InChI=1S/C16H17N9O5S2/c1-6-20-23-24(21-6)3-7-4-31-14-10(13(27)25(14)11(7)15(28)29)19-12(26)9(22-30-2)8-5-32-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,26)(H,28,29)/b22-9-/t10-,14-/m1/s1
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| Chemical Name |
(6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-[(5-methyl-2H-tetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
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| Synonyms |
Antibiotic T 2525; Cefteram; Cefterame; Ceftetrame; Ro 19-5247; Ro-19-5247; Ro19-5247; T2525; T 2525; T2525; Ro 195247; Ro-195247; Ro195247;
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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 Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0855 mL | 10.4277 mL | 20.8555 mL | |
| 5 mM | 0.4171 mL | 2.0855 mL | 4.1711 mL | |
| 10 mM | 0.2086 mL | 1.0428 mL | 2.0855 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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