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Flucloxacillin Basic information
Flucloxacillin Chemical Properties
Flucloxacillin Usage And Synthesis
  • OriginatorFloxapen,Beecham,UK,1970
  • UsesAntibacterial.
  • DefinitionChEBI: A penicillin compound having a 6beta-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamido] side-chain.
  • Manufacturing Process3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carboxylicacid, MP 206° to 207°C, was obtained by chlorinating 2-chloro-6-fluorobenzaldoxime, then condensing the resulting hydroxamoyl chloride with methyl acetoacetate in methanolic sodium methoxide and hydrolyzing the resulting ester with hot alkali. The acid chloride resulted from treatment of the acid with thionyl chloride
    A suspension of 6-aminopenicillanic acid (36.4 grams) in water was adjusted to pH 7.2 by the addition of N aqueous sodium hydroxide and the resulting solution was treated with a solution of 3-(2-chloro-6-fluorophenyl)-5- methylisoxazole-4-carbonyl chloride (46.1 grams) in isobutyl methyl ketone. The mixture was stirred vigorously for 1? hours and then filtered through Dicalite. The layers were separated and the isobutyl methyl ketone layer was shaken with saturated brine. Then, precipitation of the sodium salt only took place after dilution of the mixture with ether. In this way there was obtained 60.7 grams of the penicillin sodium salt having a purity of 88% as determined by alkalimetric assay.
  • Therapeutic FunctionAntibacterial
  • Antimicrobial activityThere is complete cross-resistance with other penicillinase-stable penicillins.
  • PharmacokineticsOral absorption: c. 80%
    Cmax 250 mg (oral): 11 mg/L after 0.5–1 h
    Plasma half-life: 2 h
    Plasma protein binding: 95%
    Absorption and distribution
    It is well absorbed after oral administration and penetrates rapidly into extravascular exudates. Its high protein binding limits its diffusion, notably into the normal CSF.
    Metabolism and excretion
    Flucloxacillin is partly metabolized in the liver and about 10% of the plasma concentration is made up of metabolites. It is more slowly eliminated than cloxacillin. Some appears in the bile but about 50–80% of an oral dose is recovered from the urine, about 20% as metabolites.
  • Clinical UseUses are those of group 3 penicillins.
  • Side effectsIn patients treated by intravenous infusion, about 5% developed phlebitis by the first and 15% by the second day, after which the proportion rose dramatically. Side effects are otherwise those common to penicillins.
Flucloxacillin(5250-39-5)Related Product Information
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