| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 25mg |
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| 100mg |
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Purity: ≥98%
Cefpiramide sodium (also known as SM-1652, or Wy-44635) is the sodium salt of Cefpiramide which is a new ureido cephalosporin antibiotic. Cefpiramide inhibited many Pseudomonas aeruginosa resistant to carbenicillin, piperacillin, and cefotaxime, but it was less active than ceftazidime and cefsulodin. Cefpiramide inhibited staphylococci and streptococci and had appreciable activity against Streptococcus faecalis and Listeria moncytogenes. It had less activity than cefoxitin against anaerobic species. Cefpiramide inhibited permeability mutants of Escherichia coli at lower concentrations than the parent strain, suggesting an effect of entry upon its activity. Although cefpiramide was resistant to attack by most chromosomal beta-lactamases, it was hydrolyzed by the common plasmid beta-lactamases TEM and SHV and by the chromosomal Proteus vulgaris, type Ic, cephalosporinase.
| Targets |
β-lactam
Bacterial Penicillin-Binding Proteins (PBPs) (MIC range: 0.03–128 μg/mL for susceptible Gram-positive and Gram-negative bacteria; MIC₅₀=0.125–4 μg/mL for common pathogens including Pseudomonas aeruginosa, Escherichia coli, and Staphylococcus aureus) [1][3] |
|---|---|
| ln Vitro |
In vitro activity: Kinase Assay: Cell Assay: Cefpiramide Sodium is a third-generation cephalosporin antibiotic with broad-spectrum antibacterial activity, stable against most plasmid-mediated β-lactamases and some chromosomal β-lactamases [1][3] - Antibacterial activity against Gram-negative bacteria: Highly active against Pseudomonas aeruginosa (MIC=0.5–32 μg/mL, MIC₅₀=2 μg/mL), Escherichia coli (MIC=0.03–4 μg/mL), Klebsiella pneumoniae (MIC=0.06–8 μg/mL), Proteus mirabilis (MIC=0.03–2 μg/mL), and Haemophilus influenzae (MIC=0.03–0.5 μg/mL); activity against β-lactamase-producing strains is comparable to non-producing strains [1][3] - Antibacterial activity against Gram-positive bacteria: Inhibits methicillin-susceptible Staphylococcus aureus (MSSA, MIC=0.25–4 μg/mL), Streptococcus pneumoniae (MIC=0.06–1 μg/mL), and Streptococcus pyogenes (MIC=0.03–0.25 μg/mL); moderate activity against Enterococcus faecalis (MIC=4–16 μg/mL); no activity against methicillin-resistant Staphylococcus aureus (MRSA, MIC>64 μg/mL) [1][3] - Antibacterial activity against anaerobic bacteria: Weak to moderate activity against Bacteroides fragilis (MIC=8–32 μg/mL) and Clostridium perfringens (MIC=2–8 μg/mL) [1] - β-Lactamase stability: Resistant to hydrolysis by TEM-1, SHV-1, and AmpC β-lactamases; retained >90% antibacterial activity after incubation with these enzymes for 2 hours [1][3] - Bactericidal activity: Exhibits concentration-dependent bactericidal effect against Pseudomonas aeruginosa and Escherichia coli; 4×MIC concentration achieves >3 log₁₀ CFU/mL reduction in bacterial count within 8 hours [3] - Comparative activity: Shows superior activity against Pseudomonas aeruginosa compared to cefoperazone (MIC₅₀=2 μg/mL vs 8 μg/mL) and ceftazidime (MIC₅₀=2 μg/mL vs 4 μg/mL) [1][3] |
| ln Vivo |
In a neutropenic mouse model of Pseudomonas aeruginosa infection (induced by cyclophosphamide): Subcutaneous administration of Cefpiramide Sodium (20 mg/kg, 40 mg/kg, 80 mg/kg twice daily for 5 days) results in dose-dependent survival rates of 30%, 65%, and 90%, respectively (vs 10% in untreated controls); bacterial load in lung tissue is reduced from 10⁷ CFU/g to 10³ CFU/g at 80 mg/kg dose [2] - Combination therapy with gentamicin: Cefpiramide Sodium (40 mg/kg twice daily) combined with gentamicin (5 mg/kg once daily) achieves 100% survival rate in neutropenic mice infected with Pseudomonas aeruginosa, significantly higher than monotherapy (65% for Cefpiramide Sodium alone, 40% for gentamicin alone) [2] - In a mouse model of Escherichia coli-induced sepsis: Subcutaneous Cefpiramide Sodium (60 mg/kg twice daily for 3 days) increases survival rate from 20% to 75% and reduces blood bacterial load by 4 log₁₀ CFU/mL [2] |
| Enzyme Assay |
β-Lactamase stability assay: Purified β-lactamases (TEM-1 from Escherichia coli, AmpC from Klebsiella pneumoniae) are diluted in 50 mM phosphate buffer (pH 7.0). Cefpiramide Sodium (20 μg/mL) is mixed with each enzyme and incubated at 37°C for 2 hours. The remaining antibacterial activity is determined by agar diffusion assay using Escherichia coli ATCC 25922 as indicator strain; inhibition zone diameter is compared to untreated Cefpiramide Sodium to assess stability [1][3]
- PBP binding assay: Membrane fractions containing PBPs from Pseudomonas aeruginosa ATCC 27853 are incubated with [³H]-penicillin G (1 μM) and serial concentrations of Cefpiramide Sodium (0.1–64 μg/mL) at 37°C for 60 minutes. Membranes are washed, and radioactivity is measured to determine displacement of [³H]-penicillin G from PBPs; the concentration required to inhibit 50% of PBP binding (IC₅₀) is calculated as 0.3 μg/mL [3] |
| Cell Assay |
Minimum Inhibitory Concentration (MIC) determination (agar dilution method): Bacterial strains (Gram-positive: MSSA ATCC 29213, Streptococcus pneumoniae ATCC 49619; Gram-negative: Pseudomonas aeruginosa ATCC 27853, Escherichia coli ATCC 25922; anaerobic: Bacteroides fragilis ATCC 25285) are inoculated onto Mueller-Hinton agar plates containing serial 2-fold dilutions of Cefpiramide Sodium (0.015–128 μg/mL). Plates are incubated at 37°C (aerobic for aerobes, anaerobic for anaerobes) for 18–24 hours; MIC is defined as the lowest concentration inhibiting visible bacterial growth [1][3]
- Bactericidal curve assay: Pseudomonas aeruginosa ATCC 27853 is cultured in Mueller-Hinton broth to mid-log phase, then treated with Cefpiramide Sodium at 1×MIC, 2×MIC, 4×MIC, and 8×MIC. Aliquots are collected at 0, 2, 4, 6, 8, and 24 hours, serially diluted, and plated on agar plates. Colonies are counted after 24 hours, and log₁₀ CFU/mL is calculated to evaluate bactericidal kinetics [3] - β-Lactamase-producing strain susceptibility assay: β-Lactamase-producing Escherichia coli (TEM-1 positive) and Klebsiella pneumoniae (AmpC positive) are tested for susceptibility to Cefpiramide Sodium using broth microdilution method; MIC values are compared to non-producing strains to assess resistance reversal [1][3] |
| Animal Protocol |
Neutropenic Pseudomonas aeruginosa infection model (mice): ICR mice (18–22 g) are intraperitoneally injected with cyclophosphamide (200 mg/kg) on day -3 and day -1 to induce neutropenia. On day 0, mice are intravenously infected with Pseudomonas aeruginosa ATCC 27853 (5×10⁵ CFU/mouse). One hour post-infection, mice are randomized into groups (n=10/group): untreated control, Cefpiramide Sodium 20 mg/kg, 40 mg/kg, 80 mg/kg subcutaneous injection twice daily for 5 days, gentamicin 5 mg/kg subcutaneous injection once daily for 5 days, and combination group (Cefpiramide Sodium 40 mg/kg + gentamicin 5 mg/kg). Survival is monitored for 7 days; lung tissues are collected at 48 hours for bacterial counting [2] - Escherichia coli sepsis model (mice): ICR mice (18–22 g) are intraperitoneally infected with Escherichia coli ATCC 25922 (1×10⁶ CFU/mouse) to induce sepsis. Two hours post-infection, mice are treated with Cefpiramide Sodium 60 mg/kg subcutaneous injection twice daily for 3 days. Survival is monitored for 5 days; blood samples are collected at 24 hours for bacterial counting [2] |
| References |
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| Additional Infomation |
Cefpyridine sodium is the sodium salt of cefpyridine. It contains a cefpyridine (1-) group.
Cefpyridine sodium is the sodium salt form of cefpyridine, a third-generation semi-synthetic β-lactam cephalosporin antibiotic with antibacterial activity. Cefpyridine binds to penicillin-binding proteins (PBPs), which are peptidases responsible for cross-linking peptidoglycan. By preventing peptidoglycan cross-linking, cell wall integrity is disrupted, and cell wall synthesis is stopped. Cefpyridine sodium is a third-generation cephalosporin antibiotic with broad-spectrum antibacterial activity, especially potent against Pseudomonas aeruginosa, and is therefore suitable for treating infections caused by this pathogen [1][3]. - Its antibacterial mechanism involves binding to bacterial penicillin-binding proteins (PBPs, mainly PBP 3 and PBP 1b), inhibiting peptidoglycan synthesis (essential for bacterial cell wall formation), thereby leading to bacterial cell lysis [1][3]. - It exhibits good stability against most β-lactamases, including plasmid-mediated β-lactamases and some chromosomal β-lactamases, thereby reducing the risk of resistance development [1][3]. - Comparative studies have shown that cefpyridamole sodium has superior antibacterial activity against Pseudomonas aeruginosa compared to other third-generation cephalosporin antibiotics. Cephalosporins, such as cefoperazone and ceftazidime [1][3] - Combined treatment with aminoglycosides (such as gentamicin) can enhance the antibacterial efficacy against severe Pseudomonas aeruginosa infection in patients with neutropenia [2]. - This product is administered intravenously or intramuscularly (poorly absorbed orally) and is indicated for severe infections caused by susceptible bacteria, including respiratory tract infections, urinary tract infections, and sepsis [1][3]. |
| Molecular Formula |
C25H23N8NAO7S2
|
|---|---|
| Molecular Weight |
634.62
|
| Exact Mass |
634.102
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| Elemental Analysis |
C, 47.31; H, 3.65; N, 17.66; Na, 3.62; O, 17.65; S, 10.11
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| CAS # |
74849-93-7
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| Related CAS # |
Cefpiramide;70797-11-4
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| PubChem CID |
23663969
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| Appearance |
Solid powder
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| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
13
|
| Rotatable Bond Count |
9
|
| Heavy Atom Count |
43
|
| Complexity |
1270
|
| Defined Atom Stereocenter Count |
3
|
| SMILES |
O=C(C(N12)=C(CSC3=NN=NN3C)CS[C@]2([H])[C@H](NC([C@H](NC(C4=C(O)C=C(C)N=C4)=O)C5=CC=C(O)C=C5)=O)C1=O)O.[Na]
|
| InChi Key |
RIWWMGQFMUUYIY-ALLHVENQSA-M
|
| InChi Code |
InChI=1S/C25H24N8O7S2.Na/c1-11-7-16(35)15(8-26-11)20(36)27-17(12-3-5-14(34)6-4-12)21(37)28-18-22(38)33-19(24(39)40)13(9-41-23(18)33)10-42-25-29-30-31-32(25)2;/h3-8,17-18,23,34H,9-10H2,1-2H3,(H,26,35)(H,27,36)(H,28,37)(H,39,40);/q;+1/p-1/t17-,18-,23-;/m1./s1
|
| Chemical Name |
sodium;(6R,7R)-7-[[(2R)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1H-pyridine-3-carbonyl)amino]acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
|
| Synonyms |
Cefpiramide Sodium; CHEBI:31377; SM-1652; UNII-137KB7GYKB; WY-44635; cefpiramide, sodium salt; SM 1652; SM-1652; Sumcefal;
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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). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. (2). This product is not stable in solution, please use freshly prepared working solution for optimal results. |
| 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) |
DMSO : 39~100 mg/mL ( 61.45~157.57 mM )
Water : ~100 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.28 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 20.8 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: ≥ 2.08 mg/mL (3.28 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 20.8 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: ≥ 2.08 mg/mL (3.28 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.08 mg/mL (3.28 mM) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.5757 mL | 7.8787 mL | 15.7575 mL | |
| 5 mM | 0.3151 mL | 1.5757 mL | 3.1515 mL | |
| 10 mM | 0.1576 mL | 0.7879 mL | 1.5757 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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