Flucloxacillin Chemical Properties
- Boiling point:677.3±55.0 °C(Predicted)
- Density 1.59±0.1 g/cm3(Predicted)
- pkapKa 2.7 (Uncertain)
- CAS DataBase Reference5250-39-5(CAS DataBase Reference)
Flucloxacillin Usage And Synthesis
- 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
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 Sodium Sterile/Oral FLUCLOXACILLIN SODIUM HYDRATE FLUCLOXACILLIN SODIUM HYDRATE MM(CRM STANDARD),FLUCLOXACILLIN SODIUM EPF(CRM STANDARD),FLUCLOXACILLIN SODIUM WHO(CRM STANDARD) OXACILLIN SODIUM 2-(TERT-BUTYLTHIO)ETHYLAMINE HYDROCHLORIDE N-ALPHA-METHYL-D-VALINE HYDROCHLORIDE D-CYSTEINE HYDROCHLORIDE D(-)PENICILLAMINE HYDROCHLORIDE BUTTPARK 146\50-48 OXACILLIN 1,4-Thiazepane hydrochloride DIMETHYLCYSTEAMINE HYDROCHLORIDE Flucloxacillin Sulfisoxazole PYRAZOPHOS Chlorodimethylphenylsilane Flucloxacillin sodium BP98,Sodium flucloxacillin,FLUCLOXACILLIN SODIUM Methyl
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