Size | Price | Stock | Qty |
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10g |
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25g |
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50g |
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100g |
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Other Sizes |
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Purity: ≥98%
Fosfomycin calcium (MK-0955 calcium) is a potent, blood-brain barrier penetrant phosphoenolpyruvate analog produced by Streptomyces and a synthetic broad-spectrum antibiotic with antimicrobial and bactericidal properties. Fosfomycin binds to and inactivates the enzyme enolpyruvate transferase. This leads to an irreversible blockage of the condensation of uridine diphosphate-N-acetylglucosamine with p-enolpyruvate, which is one of the first steps of bacterial cell wall synthesis.
Targets |
Bacterial cell wall synthesis
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ln Vitro |
The antibacterial agent found in epoxy is fosfomycin calcium. In contrast to other antibacterial agents, its mechanism of action involves impeding the initial stage of cell wall synthesis [1].
With an inhibition rate of 90%, fosfomycin calcium exhibits bactericidal activity against a range of gram-positive and gram-negative pathogens, including broad-spectrum producing β-Bacteria of lactamase and carbapenemase[1]. Research on infections of the central nervous system, soft tissues, bone, lungs, and abscesses can be conducted using fosfomycin calcium, which exhibits significant tissue penetration[2]. |
ln Vivo |
The protective effect of fosfomycin calcium (80 mg/kg; i.v.-i.v. or i.v.-p.o.) against the nephrotoxicity of double beckacin is demonstrated, and administration routes do not alter this effect[3].
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Enzyme Assay |
Fosfomycin is a bactericidal antibiotic agent. It inhibits an enzyme-catalyzed reaction in the first step of the synthesis of the bacterial cell wall. Fosfomycin interferes with the first cytoplasmic step of bacterial cell wall biosynthesis, the formation of the peptidoglycan precursor UDP N-acetylmuramic acid (UDP-MurNAc). Specifically, the enzyme UDP-N-acetylglucosamine enolpyruvyl transferase (MurA) is involved in peptidoglycan biosynthesis by catalyzing the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 3′-hydroxyl group of UDP-N-acetylglucosamine (UNAG). Fosfomycin covalently binds to the thiol group of a cysteine (position 115 in Escherichia coli numbering; target Cys115) in the active site of MurA and consequently inactivates it. This inhibitory action takes place at an earlier step than the action of β-lactams or glycopeptides [1].
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Cell Assay |
Fosfomycin exerts immunomodulatory effects by altering lymphocyte, monocyte and neutrophil function. It affects the acute inflammatory cytokine response in vitro and in vivo. It suppresses production of tumor necrosis factor alpha (TNF-α), interleukin-1β (IL-1β), and IL-1α and increases production of IL-10, while contradictory data have been published regarding IL-6. On the other hand, concentrations of TNF-α, IL-1β, and IL-6 expressed as protein and mRNA were almost identical with and without fosfomycin in healthy volunteers. Fosfomycin suppresses IL-2 production from T cells, the production of leukotriene B4 (LTB4) from neutrophils, and the expression of IL-8 mRNA by LTB4 from monocytes. Fosfomycin also exhibits an immunomodulatory effect on B-cell activation. Fosfomycin enhances neutrophil phagocytic killing of invading pathogens, even in patients on chronic hemodialysis and renal transplantation). Fosfomycin resulted in enhanced bactericidal ability of neutrophils compared to other antimicrobials. The clinical relevance of the aforementioned actions remains to be elucidated [1].
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Animal Protocol |
Animal Model: Fischer 344 rats[3]
Dosage: 320 mg/kg Administration: Intramuscular injection, five schedules: one hour, half an hour before dibekacin, simultaneously, half an hour after, and one hour after; eleven days Result: Dibecacin (40 mg/kg)-induced reduction in polyuria, proteinuria, enzymes, and cytosine, followed by the prior treatment. |
References |
Molecular Formula |
C3H5CAO4P
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Molecular Weight |
176.12
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Exact Mass |
175.95513
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Elemental Analysis |
C, 20.46; H, 2.86; Ca, 22.76; O, 36.34; P, 17.59
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CAS # |
26016-98-8
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Related CAS # |
Fosfomycin sodium;26016-99-9;Fosfomycin tromethamine;78964-85-9;Fosfomycin;23155-02-4
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Appearance |
White to off-white solid powder
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LogP |
0.78
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tPSA |
85.53
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SMILES |
C[C@H]1[C@@H](P(O)([O-])=O)O1.CC2C(P(O)([O-])=O)O2.[Ca+2]
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InChi Key |
DFBPVXQYQJJUMW-JSTPYPERSA-L
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InChi Code |
InChI=1S/2C3H7O4P.Ca/c2*1-2-3(7-2)8(4,5)6/h2*2-3H,1H3,(H2,4,5,6)/q+2/p-2/t2-,3+/m0../s1
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Chemical Name |
calcium hydrogen ((2R,3S)-3-methyloxiran-2-yl)phosphonate hydrogen (3-methyloxiran-2-yl)phosphonate
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Synonyms |
Calcium fosfomycin; AN-8336; CS-4631; AN8336; CS4631; AN 8336; CS 4631; Phosphomycin Calcium
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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: Please store this product in a sealed and protected environment, 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) |
H2O : ~50 mg/mL (~283.90 mM )
DMSO : < 1 mg/mL |
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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 | 5.6779 mL | 28.3897 mL | 56.7795 mL | |
5 mM | 1.1356 mL | 5.6779 mL | 11.3559 mL | |
10 mM | 0.5678 mL | 2.8390 mL | 5.6779 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.