Fosfomycin calcium
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| Category | Bioactive by-products |
| Catalog number | BBF-04008 |
| CAS | 26472-47-9 |
| Molecular Weight | 138.06 (free acid) |
| Molecular Formula | C3H7O4P.xCa |
| Purity | ≥98% |
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Description
Fosfomycin calcium is the calcium salt form of Fosfomycin, produced by Streptomyces. Fosfomycin is an antibiotic that is primarily used to treat bladder infections. Fosfomycin inhibits bacterial cell wall biogenesis by inactivating the enzyme UDP-N-acetylglucosamine-3-enolpyruvyltransferase, also known as MurA.
Specification
| Related CAS | 23155-02-4 (free acid) 26016-98-8 (monocalcium salt) 32504-47-5 (Deleted CAS) |
| Synonyms | Phosphomycin calcium; Phosphonomycin calcium; Phosphonic acid, [(2R,3S)-3-methyloxiranyl]-, calcium salt; Phosphonic acid, (1,2-epoxypropyl)-, calcium salt, cis-(-)-; Phosphonic acid, (3-methyloxiranyl)-, calcium salt, (2R-cis)- |
| Storage | Store at -20°C |
| IUPAC Name | calcium;[(2R,3S)-3-methyloxiran-2-yl]-dioxido-oxo-lambda5-phosphane |
| Canonical SMILES | CC1C(O1)P(=O)([O-])[O-].[Ca+2] |
| InChI | InChI=1S/C3H5O4P.Ca/c1-2-3(7-2)8(4,5)6;/h2-3H,1H3,(H2,4,5,6);/q;+2/p-2/t2-,3+;/m0./s1 |
| InChI Key | YMZJBJPWTXJQMR-LJUKVTEVSA-L |
Properties
| Boiling Point | 342.7°C at 760 mmHg |
| Melting Point | 250°C |
| Solubility | Soluble in DMSO |
Reference Reading
1.Elucidating the genetic basis of crystalline biofilm formation in Proteus mirabilis.
Holling N1, Lednor D, Tsang S, Bissell A, Campbell L, Nzakizwanayo J, Dedi C, Hawthorne JA, Hanlon G, Ogilvie LA, Salvage JP, Patel BA, Barnes LM, Jones BV. Infect Immun. 2014 Apr;82(4):1616-26. doi: 10.1128/IAI.01652-13. Epub 2014 Jan 27.
Proteus mirabilis forms extensive crystalline biofilms on urethral catheters that occlude urine flow and frequently complicate the management of long-term-catheterized patients. Here, using random transposon mutagenesis in conjunction with in vitro models of the catheterized urinary tract, we elucidate the mechanisms underpinning the formation of crystalline biofilms by P. mirabilis. Mutants identified as defective in blockage of urethral catheters had disruptions in genes involved in nitrogen metabolism and efflux systems but were unaffected in general growth, survival in bladder model systems, or the ability to elevate urinary pH. Imaging of biofilms directly on catheter surfaces, along with quantification of levels of encrustation and biomass, confirmed that the mutants were attenuated specifically in the ability to form crystalline biofilms compared with that of the wild type. However, the biofilm-deficient phenotype of these mutants was not due to deficiencies in attachment to catheter biomaterials, and defects in later stages of biofilm development were indicated.
2.The revival of fosfomycin.
Michalopoulos AS1, Livaditis IG, Gougoutas V. Int J Infect Dis. 2011 Nov;15(11):e732-9. doi: 10.1016/j.ijid.2011.07.007. Epub 2011 Sep 25.
Fosfomycin, originally named phosphonomycin, was discovered in Spain in 1969. There are three forms of fosfomycin: fosfomycin tromethamine (a soluble salt) and fosfomycin calcium for oral use, and fosfomycin disodium for intravenous use. Fosfomycin is a bactericidal antibiotic that interferes with cell wall synthesis in both Gram-positive and Gram-negative bacteria by inhibiting the initial step involving phosphoenolpyruvate synthetase. It has a broad spectrum of activity against a wide range of Gram-positive and Gram-negative bacteria. It is highly active against Gram-positive pathogens such as Staphylococcus aureus and Enterococcus, and against Gram-negative bacteria such as Pseudomonas aeruginosa and Klebsiella pneumoniae. Its unique mechanism of action may provide a synergistic effect to other classes of antibiotics including beta-lactams, aminoglycosides, and fluoroquinolones. Oral fosfomycin is mainly used in the treatment of urinary tract infections, particularly those caused by Escherichia coli and Enterococcus faecalis.
3.Quantitative 31P-NMR spectroscopy for the determination of fosfomycin and impurity A in pharmaceutical products of fosfomycin sodium or calcium.
Jiang H1, Chen H2, Cai N2, Zou J1, Ju X2. Magn Reson Chem. 2015 Jun;53(6):454-9. doi: 10.1002/mrc.4224. Epub 2015 Apr 9.
A quantitative 31P-NMR method for the determination of fosfomycin and impurity A in pharmaceutical products of fosfomycin sodium or calcium has been developed. In this method, coaxial inserts containing trimethyl phosphate are used as external standard. The method is convenient and robust, and gives both high accuracy and precision. It is shown that an accurate determination is possible using different probes and coaxial inserts.
4.The efficacy of a hydroxyapatite composite as a biodegradable antibiotic delivery system.
Buranapanitkit B1, Srinilta V, Ingviga N, Oungbho K, Geater A, Ovatlarnporn C. Clin Orthop Relat Res. 2004 Jul;(424):244-52.
Local biodegradable carriers have been studied for use as a skeletal drug delivery system. This study investigated the efficacy of a local biodegradable composite composed of hydroxyapatite, plaster of Paris, and chitosan impregnated with antibiotics to treat methicillin-resistant Staphylococcus aureus. The composite, impregnated with vancomycin, fosfomycin, or sodium fusidate was tested for its sustained elution characteristics during 3 months and compared with similarly impregnated polymethylmethacrylate using the modified disc diffusion technique. Physicochemical properties using scanning electron microscopy and xray diffraction analysis of each preparation also were analyzed. Vancomycin and fosfomycin incorporated into the hydroxyapatite composite inhibited the organism for 3 months, whereas sodium fusidate was effective only for 3 weeks. Vancomycin and fosfomycin loaded into the hydroxyapatite composite had a significantly better inhibitive effect than when loaded in polymethylmethacrylate, whereas sodium fusidate loaded in polymethylmethacrylate showed a significantly better inhibitive effect than when loaded in the hydroxyapatite composite.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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