| Size | Price | Stock | Qty |
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| 1mg |
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| Other Sizes |
| Targets |
Penicillin-binding proteins (PBPs). Phenethicillin, like other penicillins, binds to and inactivates penicillin-binding proteins (PBPs), which are transpeptidase enzymes involved in the cross-linking of the peptidoglycan layer of the bacterial cell wall. Inhibition of PBPs leads to cell wall weakening, osmotic instability, and bacterial cell lysis. It primarily targets Gram-positive bacteria, including Streptococcus and Staphylococcus species (except beta-lactamase-producing strains). Phenethicillin (alpha-Phenoxyethylpenicillin) sodium is a penicillin and has antimicrobial activity.
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| ln Vitro |
Phenethicillin exhibits antimicrobial activity against Gram-positive bacteria, including Streptococcus pyogenes, Streptococcus pneumoniae, and non-penicillinase-producing Staphylococcus aureus. Minimum inhibitory concentrations (MICs) for susceptible strains typically range from 0.125-1 ug/mL. It is less active against Gram-negative bacteria due to poor penetration of the outer membrane and susceptibility to beta-lactamases. It is not active against beta-lactamase-producing strains. It is used as a reference compound in antibiotic susceptibility studies.
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| ln Vivo |
In vivo, Phenethicillin sodium is effective in treating infections caused by susceptible Gram-positive bacteria. It has been used clinically for respiratory tract infections (e.g., streptococcal pharyngitis, tonsillitis), skin and soft tissue infections, and dental infections. Its acid stability makes it suitable for oral administration. It is largely replaced by more modern antibiotics but remains relevant in microbiological research. In animal models, it is effective against Streptococcus pyogenes and S. aureus infections. Phenethicillin (alpha-Phenoxyethylpenicillin) sodium is a penicillin and has antimicrobial activity.
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| Enzyme Assay |
For cell-free binding assays, purified penicillin-binding proteins (PBPs) from bacterial membranes (e.g., S. aureus or S. pneumoniae) are prepared as described for other beta-lactams. Bacterial cells are lysed, and the membrane fraction is isolated by ultracentrifugation. The membrane fraction (50-100 ug protein) is incubated with various concentrations of Phenethicillin sodium (0.1 nM-100 uM) in 50 mM potassium phosphate buffer (pH 7.0) at 30degC for 10-30 minutes. A radiolabeled penicillin (e.g., 14C-benzylpenicillin) is then added and incubated for another 10 minutes. The reaction is stopped with SDS-PAGE sample buffer and boiling. Samples are separated by SDS-PAGE, and the gel is dried and exposed to a phosphorimager screen. The intensity of the PBP bands is quantified. The IC50 for each PBP is determined. Phenethicillin has the highest affinity for PBP1 and PBP3 in S. aureus. For susceptibility testing by broth microdilution, standard CLSI protocols are used.
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| Cell Assay |
For in vitro antibacterial assays, standard bacterial strains (e.g., S. aureus ATCC 29213, S. pneumoniae ATCC 49619, S. pyogenes ATCC 19615) are cultured in cation-adjusted Mueller-Hinton broth (with 5% lysed horse blood for streptococci) to achieve a density of 5×10⁵ CFU/mL. Phenethicillin sodium is serially diluted (0.001-100 ug/mL) in 96-well plates in appropriate medium. Bacterial suspension is added, and plates are incubated at 35degC for 18-24 hours. The minimum inhibitory concentration (MIC) is the lowest concentration that prevents visible growth. For time-kill assays, S. aureus cultures are treated with Phenethicillin at 1×, 2×, and 4× MIC, and viable bacterial counts are determined by plating at 0, 2, 4, 6, 12, and 24 hours. Phenethicillin exhibits concentration-dependent killing. For detection of beta-lactamase activity, nitrocefin (a chromogenic cephalosporin) can be used. A yellow-to-red color change indicates hydrolysis of the beta-lactam ring, indicating resistance.
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| Animal Protocol |
No specific in vivo animal study protocols are documented for Phenethicillin sodium. A typical protocol for evaluating a penicillin antibiotic would involve using a murine systemic infection model. Female ICR mice (6-8 weeks old, 18-22 g) are challenged intraperitoneally with a lethal dose of S. aureus (e.g., 10⁸ CFU/mouse) or S. pyogenes (10⁷ CFU/mouse) suspended in 5% mucin. One hour post-infection, Phenethicillin sodium is administered orally or subcutaneously at doses of 10-200 mg/kg. Survival is monitored for 7 days. ED50 values are calculated by probit analysis. In a murine thigh infection model, neutropenic mice are infected intramuscularly with 10⁵-10⁶ CFU of S. aureus. Phenethicillin is administered orally at various doses. After 24 hours, mice are euthanized, and thigh muscles are homogenized for bacterial CFU enumeration. Efficacy is expressed as log10 reduction in CFU/g compared to untreated controls.
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| ADME/Pharmacokinetics |
Phenethicillin sodium is administered orally. It is acid-stable, so it is well absorbed from the gastrointestinal tract. In humans, peak plasma concentrations (Cmax) of 2-5 ug/mL are achieved within 1-2 hours after an oral dose of 250-500 mg. The plasma half-life is approximately 30-60 minutes. It is excreted primarily unchanged in urine by glomerular filtration and tubular secretion. Probenecid (a uricosuric agent) can inhibit renal tubular secretion, increasing plasma concentrations and prolonging half-life. The sodium salt formulation enhances aqueous solubility for parenteral administration. Phenethicillin is largely replaced by more modern oral penicillins such as amoxicillin.
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| Toxicity/Toxicokinetics |
Phenethicillin sodium is generally well tolerated. Common adverse effects include gastrointestinal disturbances (nausea, vomiting, diarrhea), rash, urticaria, and hypersensitivity reactions (including anaphylaxis) in penicillin-allergic patients. As with other penicillins, it can cause antibiotic-associated diarrhea and, rarely, Clostridium difficile-associated colitis (pseudomembranous colitis). High doses may cause neurotoxicity (seizures) in patients with renal impairment. The LD50 in mice is >2000 mg/kg. It is a prescription antibiotic, not for research use in vivo without appropriate approvals.
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| References |
[1]. Timmers GJ, et al. Levofloxacin vs. ciprofloxacin plus phenethicillin for the prevention of bacterial infections in patients with haematological malignancies. Clin Microbiol Infect. 2007 May;13(5):497-503.
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| Additional Infomation |
Phenethicillin sodium is also known as alpha-Phenoxyethylpenicillin sodium and Pheneticillin sodium. The molecular formula is C17H19N2NaO5S, and the molecular weight is 386.40. It is a beta-lactam antibiotic belonging to the penicillin class. It was introduced in the 1960s for oral treatment of staphylococcal and streptococcal infections. It is largely replaced by more modern antibiotics (e.g., amoxicillin, cephalexin). It is used as a reference compound in antimicrobial susceptibility testing and antibiotic resistance research. It is not approved for use in many countries. For research use only. IUPAC name: sodium;(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxypropanoylamino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate.
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| Molecular Formula |
C17H19N2NAO5S
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| Molecular Weight |
386.40
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| Exact Mass |
386.091
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| CAS # |
30302-52-4
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| PubChem CID |
139025655
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| Appearance |
Typically exists as solid at room temperature
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
26
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| Complexity |
582
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CC(C(=O)N[C@H]1C2N(C1=O)[C@H](C(S2)(C)C)C(=O)[O-])OC3=CC=CC=C3.[Na+]
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| InChi Key |
HZRQUJWXQAEVBK-BWVWTODUSA-M
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| InChi Code |
InChI=1S/C17H20N2O5S.Na/c1-9(24-10-7-5-4-6-8-10)13(20)18-11-14(21)19-12(16(22)23)17(2,3)25-15(11)19;/h4-9,11-12,15H,1-3H3,(H,18,20)(H,22,23);/q;+1/p-1/t9?,11-,12+,15?;/m1./s1
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| Chemical Name |
sodium;(2S,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxypropanoylamino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
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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) |
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 | 2.5880 mL | 12.9400 mL | 25.8799 mL | |
| 5 mM | 0.5176 mL | 2.5880 mL | 5.1760 mL | |
| 10 mM | 0.2588 mL | 1.2940 mL | 2.5880 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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