Dicloxacillin sodium Chemical Properties
- Melting point:222-225°C
- alpha D20 +127.2° (water)
- storage temp. 2-8°C
- solubility H2O: soluble50mg/mL
- form powder
- color white to off-white
- Water Solubility Soluble in water
- BRN 4778711
- CAS DataBase Reference13412-64-1(CAS DataBase Reference)
Dicloxacillin sodium Usage And Synthesis
- Brand Name(s) in USDynapen
- Chemical PropertiesWhite to off-white crystalline powder
- UsesDicloxacillin sodium salt is used in the treatment of staphylococci resistant to penicillin G. Dicloxacillin binds to specific penicillin-binding proteins in the bacterial cell wall and therefore inhibits the last stage of bacterial cell wall synthesis. Cell lysis, mediated by bacterial cell wall autolytic enzymes, is the result. Dicloxacillin may interfere with autolysin inhibitors.
- UsesA semi-synthetic antibiotic related to Penicillin. Antibacterial.
- UsesAntibacterial;Bacterial transpeptidase inhibitor
- Manufacturing ProcessA suspension of 6-aminopenicillanic acid (216 grams) in water (2 liters) was
adjusted to pH 6.8 by the addition of N aqueous sodium hydroxide
(approximately 1 liter) and the resulting solution was stirred vigorously while
a solution of 3-(2',6'-dichlorophenyl)-5-methylisoxazole-4-carbonyl chloride
(290 grams) in acetone (1.5 liters) was added in one portion.
The temperature rose to 26°C and as reaction proceeded the free acid form of the penicillin separated as a white solid. After 30 minutes the suspension was cooled to 10°C and stirring was continued at this temperature for 1 hour more. The mixture was then cooled to 0°C, centrifuged, and the solid product washed with aqueous acetone (250 ml) and finally dried in an air oven at 30°C. The product (440 grams, 94%) had [α]D20 +106.3° (c 1 in EtOH) and was shown by alkalimetric assay to be 97.5% pure.
The salt was prepared by dissolving the free acid form of the penicillin in the equivalent amount of aqueous sodium bicarbonate and freeze drying the resulting solution. The hydrated salt so obtained was shown by alkalimetric assay to be 94% pure and to contain 6% water.
- brand nameDynapen (Apothecon).
- Therapeutic FunctionAntibacterial
- General DescriptionThe substitution of chlorine atoms on both carbons orthoto the position of attachment of the phenyl ring to the isoxazolering is presumed to enhance further the stability ofthe oxacillin congener dicloxacillin sodium, [3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolyl]penicillin sodiummonohydrate (Dynapen, Pathocil, Veracillin) and toproduce high plasma concentrations of it. Its medicinalproperties and use are similar to those of cloxacillinsodium. Progressive halogen substitution, however, alsoincreases the fraction bound to protein in the plasma, potentiallyreducing the concentration of free antibiotic inplasma and tissues. Its medicinal properties and use are thesame as those of cloxacillin sodium.
- Veterinary Drugs and TreatmentsThe veterinary use of dicloxacillin has been primarily in the PO treatment of bone, skin, and other soft tissue infections in small animals when penicillinase-producing Staphylococcus species have been isolated. Because of its low oral bioavailability and short halflife, other drugs with good staph coverage are usually employed.
Dicloxacillin sodium Preparation Products And Raw materials
6-Aminopenicillanic acid Dicloxacillin EP Impurity B N-[[3-(2,6-Dichlorophenyl)-5-Methyl-4-isoxazolyl]carbonyl]glycine [3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolyl]carbonyl N3-[N-[[3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]glycinyl]penicilloic Acid Dicloxacillin Sodium impurity A 3-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carboxylic acid DICLOXACILLIN SODIUM IMP. C (EP): 6-AMINOPENICILLANIC ACID MM(CRM STANDARD) DICLOXACILLIN SODIUM MONOHYDRATE,DICLOXACILLIN SODIUM HYDRATE,DICLOXACILLIN SODIUM SALT, MONOHYDRATE,DICLOXACILLIN SODIUM SALT HYDRATE DICLOXACILLIN SODIUM, COMPACTED Dicloxacillin Sodium Sterile/Oral Parathion-methyl Methyl Oxacillin sodium monohydrate Flucloxacillin sodium OXACILLIN SODIUM Disodium phosphonomycin Rifamycin Sodium Cloxacillin-13C4 SodiuM Salt
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