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Dicloxacillin sodium

CAS No.
13412-64-1
Chemical Name:
Dicloxacillin sodium
Synonyms
Dicloxacillin sodium;Dicloxacillin sodium CRS;Dicloxacillin Sodium (500 mg);Dicloxacillin Sodium (300 mg);icloxacillinsodiummonohydrate;Dicloxacillin sodium USP/EP/BP;Dicloxacillin Sodium (1189009);DICLOXACILLIN SODIUM WHO(CRM STANDARD);DICLOXACILLIN SODIUM USP(CRM STANDARD);DICLOXACILLIN SODIUM EPD(CRM STANDARD)
CBNumber:
CB4679268
Molecular Formula:
C19H20Cl2N3NaO6S
Molecular Weight:
512.33
MDL Number:
MFCD00167147
MOL File:
13412-64-1.mol
Last updated:2024-10-28 23:16:16

Dicloxacillin sodium 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)
FDA UNII 4HZT2V9KX0

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Danger
Hazard statements  H315-H319-H334-H335
Precautionary statements  P261-P264-P271-P302+P352-P304+P340+P312-P305+P351+P338
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)
NFPA 704
0
2 0

Dicloxacillin sodium price More Price(21)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 46182 Dicloxacillin sodium salt hydrate VETRANAL 13412-64-1 100mg $59.5 2024-03-01 Buy
Sigma-Aldrich 1189009 Dicloxacillin sodium United States Pharmacopeia (USP) Reference Standard 13412-64-1 300mg $436 2024-03-01 Buy
Alfa Aesar J61581 Dicloxacillin sodium salt monohydrate 13412-64-1 1g $73.4 2024-03-01 Buy
Alfa Aesar J61581 Dicloxacillin sodium salt monohydrate 13412-64-1 5g $197.65 2024-03-01 Buy
Cayman Chemical 23770 Dicloxacillin (sodium salt hydrate) ≥98% 13412-64-1 1g $57 2024-03-01 Buy
Product number Packaging Price Buy
46182 100mg $59.5 Buy
1189009 300mg $436 Buy
J61581 1g $73.4 Buy
J61581 5g $197.65 Buy
23770 1g $57 Buy

Dicloxacillin sodium Chemical Properties,Uses,Production

Brand Name(s) in US

Dynapen

Chemical Properties

White to off-white crystalline powder

Originator

Dynapen,Bristol,US,1968

Uses

Antibacterial;Bacterial transpeptidase inhibitor

Uses

A semi-synthetic antibiotic related to Penicillin. Antibacterial.

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.

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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View Lastest Price from Dicloxacillin sodium manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Dicloxacillin Sodium hydrate pictures 2024-10-28 Dicloxacillin Sodium hydrate
13412-64-1
US $72.00-50.00 / mg 98.98% 10g TargetMol Chemicals Inc.
Dicloxacillin Sodium hydrate pictures 2024-10-28 Dicloxacillin Sodium hydrate
13412-64-1
US $72.00-50.00 / mg 98.98% 10g TargetMol Chemicals Inc.
Dicloxacillin sodium pictures 2023-09-01 Dicloxacillin sodium
13412-64-1
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
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 4-Thia-1-azabicyclo3.2.0heptane-2-carboxylic acid, 6-3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonylamino-3,3-dimethyl-7-oxo-, monosodium salt, monohydrate, (2S,5R,6R)- Dicloxacillin sodium monohydrate/Mesterolone Monosodium (2S,5R,6R)-6-(3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (2S,5R,6R)-6-[[[3-(2,6-Dichlorophenyl)-5-Methyl-4-isoxazolyl]carbonyl]aMino]-3,3- diMethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid SodiuM Salt Hydrate Dicloxacillin Sodium (500 mg) Dicloxacillin Sodium (300 mg) Dicloxacillin sodium hydrate solution,100ppm 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[[[3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-,sodium salt, hydrate Dicloxacillin Sodium Salt Monohydrate Standard Dicloxacillin sodium CRS icloxacillinsodiummonohydrate Dicloxacillin sodium USP/EP/BP Dicloxacillin Sodium (1189009) Dicloxacillin Sodium hydrate,Dicloxacillin sodium salt,inhibit,Antibiotic,Bacterial,sepsis,peritonitis,Inhibitor,Dicloxacillin Sodium Sodium (2S,5R,6R)-6-(3-(2,6-dichlorophenyl)-5-methylisoxazole-4-carboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrate Dicloxacillin sodium hydrate in ACN:H2O (9:1) C12560500 Dicloxacillin sodium hydrate 13412-64-1 3412-64-1 C19H18Cl2N3NaO6S C19H16Cl2N3O5SNaxH2O C19H16Cl2N3NaO5SxH2O C19H17Cl2N3O5SNa C19H16Cl2N3NaO5SH2O 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