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Fosfomycin

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Fosfomycin Basic information
Fosfomycin Chemical Properties
  • Melting point:94°C
  • Boiling point:342.7±52.0 °C(Predicted)
  • Density 1.56±0.1 g/cm3(Predicted)
  • pka3.20±0.40(Predicted)
  • form solid
  • CAS DataBase Reference23155-02-4(CAS DataBase Reference)
Fosfomycin Usage And Synthesis
  • Mode of actionThe N-acetylmuramic acid component of the bacterial cell wall is derived from N-acetylglucosamine by the addition of a lactic acid substituent derived from phosphoenolpyruvate. Fosfomycin blocks this reaction by inhibiting the pyruvyl transferase enzyme involved. The antibiotic enters bacteria by utilizing active transport mechanisms for α-glycerophosphate and glucose-6-phosphate. Glucose-6-phosphate induces the hexose phosphate transport pathway in some organisms (notably Escherichia coli) and potentiates the activity of fosfomycin against these bacteria.
  • Chemical PropertiesWater-soluble crystals.
  • OriginatorFosfocin,Crinos,Italy,1977
  • UsesAntibacterial.
  • DefinitionChEBI: A phosphonic acid having an (R,S)-1,2-epoxypropyl group attached to phosphorus.
  • Manufacturing Process(A) The preparation of [(1-chloroethoxy)chloromethyl]phosphonic acid: Acetaldehyde (1.1 mol) and hydroxymethylphosphonic acid (1 mol) in 500 ml of benzene are saturated with hydrogen chloride gas at 10°C to 15°C. The mixture is aged at 25°C for 24 hr, the solvent distilled out in vacuo and the residue flushed three times with benzene to remove all traces of hydrogen chloride. The residue is taken up in benzene (500 ml), treated with tert-butyl hypochlorite (0.8 mol) and azobisisobutyronitrile (0.8 mm) at 40°C until titration shows the absence of hypochlorite and the solution is then evaporated to yield [(1-chloroethoxy)chloromethyl] phosphonic acid in the form of an oil.
    (B) The preparation of (cis-1,2-epoxypropyl)phosphonic acid: [(1- chloroethoxy)chloromethyl] phosphonic acid (1.0 g) is added with stirring to tetrahydrofuran (50 ml) to which has been added a crystal of iodine and a zinc-copper couple (15.0 g). The mixture is then heated under reflux for 24 hr and the resulting solution filtered to yield (cis-1,2-epoxypropyl)-phosphonic acid.
    There is also a fermentation route to Fosfomycin as noted by Kleeman and Engel.
  • Therapeutic FunctionAntibiotic
  • Clinical UsePhosphomycin, introduced in 1972, inhibits enolpyruvial transferase, an enzyme catalyzing an early step in bacterial cell wall biosynthesis. Inhibition results in reduced synthesis of peptidoglycan, an important component in the bacterial cell wall. Phosphomycin is bactericidal against Escherichi a coli and Enterobacter faecali s infections.
Fosfomycin Preparation Products And Raw materials
Fosfomycin(23155-02-4)Related Product Information
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