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Dicloxacillin sodium

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CAS:13412-64-1
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CAS:13412-64-1
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  • 2026-03-20
  • CAS:13412-64-1
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Dicloxacillin sodium Basic information
Brand Name(s) in US
Product Name:Dicloxacillin sodium
Synonyms:3-(2,6-DICHLOROPHENYL)-5-METHYL-4-ISOXAZOLYL PENICILLIN;DICLOXACILLIN SODIUM SALT HYDRATE VETRAN;DICLOXACILLIN SODIUM EPD(CRM STANDARD);DICLOXACILLIN SODIUM USP(CRM STANDARD);DICLOXACILLIN SODIUM WHO(CRM STANDARD);Dicloxacillin monohydrate sodium salt;Dicloxacillin sodium;Sodium 7-[3-(2,6-dichlorophenyl)-5-methyl-oxazol-4-yl]carbonylamino-3,3-dimet hyl-6-oxo-2-thia-5-azabicyclo[3.2.0]heptane-4-carboxylate
CAS:13412-64-1
MF:C19H20Cl2N3NaO6S
MW:512.33
EINECS:603-794-2
Product Categories:Diclocil;Peptide Synthesis/Antibiotics;Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;APIs;A - KAntibiotics;Antibacterial;Antibiotics A to;Antibiotics A-FAntibiotics;Chemical Structure Class;Interferes with Cell Wall SynthesisAntibiotics;Mechanism of Action;Penicillins and Cephalosporins (beta-Lactams);Spectrum of Activity
Mol File:13412-64-1.mol
Dicloxacillin sodium Structure
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
Major Applicationclinical testing
InChIKeySIGZQNJITOWQEF-VICXVTCVSA-M
SMILES[Na+].[H]O[H].Cc1onc(c1C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)C([O-])=O)-c4c(Cl)cccc4Cl
CAS DataBase Reference13412-64-1(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
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Resp. Sens. 1
Skin Irrit. 2
STOT SE 3
ToxicityLD50 in mice (g/kg): 0.9 i.v.; in rats (g/kg): 0.63 i.p.; >5 orally (Gloxhuber)
MSDS Information
Dicloxacillin sodium Usage And Synthesis
Brand Name(s) in USDynapen
Chemical PropertiesWhite to off-white crystalline powder
OriginatorDynapen,Bristol,US,1968
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
DefinitionChEBI: Dicloxacillin sodium monohydrate is a hydrate. It contains a dicloxacillin sodium.
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.
Biological ActivityDocloxacillin binds to specific penicillin-binding proteins (PBPs) 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 .
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.
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