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

Stability:

Hygroscopic

CAS DataBase Reference

13412-64-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-42/43

Safety Statements 

22-26-36/37-45

WGK Germany 

2

RTECS 

XH8925000

HS Code 

29411099

Toxicity

LD50 in mice (g/kg): 0.9 i.v.; in rats (g/kg): 0.63 i.p.; >5 orally (Gloxhuber)

Dicloxacillin sodium Usage And Synthesis

Brand Name(s) in US

Dynapen

Chemical Properties

White to off-white crystalline powder

Originator

Dynapen,Bristol,US,1968

Uses

Dicloxacillin 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.

Uses

Antibacterial;Bacterial transpeptidase inhibitor

Uses

A semi-synthetic antibiotic related to Penicillin. Antibacterial.

Definition

ChEBI: Dicloxacillin sodium monohydrate is a hydrate. It contains a dicloxacillin sodium.

Manufacturing Process

A 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 name

Dynapen (Apothecon).

Therapeutic Function

Antibacterial

General Description

The 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 Treatments

The 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.

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