13412-64-1 Usage
Description
Dicloxacillin sodium is a semi-synthetic antibiotic derived from penicillin, characterized by the presence of chlorine atoms on both carbons ortho to the position of attachment of the phenyl ring to the isoxazole ring. This structural feature is believed to enhance the stability of the oxacillin congener and produce high plasma concentrations. It is a white to off-white crystalline powder with medicinal properties and uses similar to those of cloxacillin sodium.
Uses
Used in Pharmaceutical Industry:
Dicloxacillin sodium is used as an antibacterial agent for the treatment of infections caused by staphylococci resistant to penicillin G. It functions as a bacterial transpeptidase inhibitor, binding to specific penicillin-binding proteins in the bacterial cell wall and inhibiting the last stage of bacterial cell wall synthesis. This leads to cell lysis mediated by bacterial cell wall autolytic enzymes, and dicloxicillin may also interfere with autolysin inhibitors.
Brand Names:
In the United States, dicloxicillin sodium is known by the brand name Dynapen, which is manufactured by Apothecon.
Originator
Dynapen,Bristol,US,1968
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.
Therapeutic Function
Antibacterial
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.
Check Digit Verification of cas no
The CAS Registry Mumber 13412-64-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,4,1 and 2 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 13412-64:
(7*1)+(6*3)+(5*4)+(4*1)+(3*2)+(2*6)+(1*4)=71
71 % 10 = 1
So 13412-64-1 is a valid CAS Registry Number.
InChI:InChI=1/C19H17Cl2N3O5S.H2O/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24;/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28);1H2/t13-,14+,17?;/m0./s1
13412-64-1Relevant articles and documents
Process for the activation of carboxylic acids
-
, (2008/06/13)
A process for the activation of carboxylic acids which is useful for the subsequent conversion of said carboxylic acids into their corresponding amides or esters, based on reacting a 2-oxazolidinone with phosphorus pentachloride and subsequent addition of a salt of the carboxylic acid to be activated.