Dicloxacillin sodium

Bezeichnung:Dicloxacillin sodium

CAS-Nr13412-64-1

Englisch Name:Dicloxacillin sodium

CBNumberCB4679268

SummenformelC19H20Cl2N3NaO6S

Molgewicht512.33

MOL-Datei13412-64-1.mol

Dicloxacillin sodium physikalisch-chemischer Eigenschaften

Schmelzpunkt	222-225°C
alpha	D20 +127.2° (water)
storage temp.	2-8°C
Löslichkeit	H2O: soluble50mg/mL
Aggregatzustand	powder
Farbe	white to off-white
Wasserlöslichkeit	Soluble in water
BRN	4778711
Stabilität	Hygroscopic
CAS Datenbank	13412-64-1(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	36/37/38-42/43
S-Sätze:	22-26-36/37-45
WGK Germany	2
RTECS-Nr.	XH8925000
HS Code	29411099
Toxizität	LD50 in mice (g/kg): 0.9 i.v.; in rats (g/kg): 0.63 i.p.; >5 orally (Gloxhuber)

Gefahreninformationscode (GHS)

Dicloxacillin sodium Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Chemische Eigenschaften
White to off-white crystalline powder
Originator
Dynapen,Bristol,US,1968
Verwenden
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.
Verwenden
Antibacterial;Bacterial transpeptidase inhibitor
Verwenden
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.
Trademarks
Dynapen (Apothecon).
Therapeutic Function
Antibacterial
Allgemeine Beschreibung
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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