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Dicloxacillin

Dicloxacillin Structure
Dicloxacillin
  • CAS No.3116-76-5
  • Chemical Name:Dicloxacillin
  • CBNumber:CB6704937
  • Molecular Formula:C19H17Cl2N3O5S
  • Formula Weight:470.33
  • MOL File:3116-76-5.mol
Dicloxacillin Property
  • Melting point 218 °C (decomp)
  • Boiling point 692.4±55.0 °C(Predicted)
  • Density 1.62±0.1 g/cm3(Predicted)
  • storage temp. 2-8°C
  • pka pKa 2.76(H2O t=37 I=0.15 (KCl)) (Uncertain)
  • Water Solubility 3.63 mg/L
  • CAS DataBase Reference 3116-76-5(CAS DataBase Reference)
  • FDA UNII COF19H7WBK
  • ATC code J01CF01
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal word
  • Hazard statements
  • Precautionary statements

Dicloxacillin Chemical Properties,Usage,Production

  • Description Chemically this is 3(2,6-dichlorophenyl)-5-methyl-4-isoxazolyl penicillin. It differs from cloxacillin by having two chloride ions attached to the phenyl group. It comes as oral capsules of 250 and 500 mg, and in an injectable formulation of 500 mg and 1 g.
  • Originator Dynapen,Bristol,US,1968
  • Uses Antibacterial.
  • Definition ChEBI: A penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]formyl group.
  • 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
  • Antimicrobial activity It is very highly bound to serum protein, and its activity in the presence of human serum in vitro is depressed to a greater extent than that of other isoxazolylpenicillins.
  • General Description Dicloxacillin was synthesized by Bayer in 1965 starting with 6-aminopenicillanic acid. It is a penicillinase-stable and orally active semisynthetic penicillin and shows higher and longer serum concentrations than cloxacillin when administered orally. Dicloxacillin is used orally, either alone or in combination with ampicillin, to treat various infections, including those caused by benzylpenicillin-resistant bacteria.
  • Pharmacology In terms of mechanism of action, antibacterial spectrum, and indications for use, it is essentially no different than oxacillin and cloxacillin. Synonyms of this drug are diclocil, novapen, diclex, and others.
    The following type of semisynthetic penicillins that should be considered are those in which amino acids, mainly α-aminophenylacetic or p-oxy-α-amino-phenylacetic acids, act as the acyl radical (ampicillin, amoxacillin).
    The antimicrobial spectrum of aminopenicillins is similar to penicillin G, with the exception that they also act on a number of Gram-negative microorganisms. Both aminopenicillins are destroyed by staphylococcus penicillinase.
  • Pharmacokinetics Oral absorption: c. 50%
    Cmax , 250 mg oral: 9 mg/L after 1 h
    500 mg intramuscular: 14–16 mg/L after 0.5–1 h
    Plasma half-life: 0.5 h
    Plasma protein binding: 95–97%
    Absorption
    Absorption in the very young is poor and unpredictable.
    Metabolism and excretion
    Dicloxacillin is partly metabolized in the liver and about 10% of the circulating drug is in the form of metabolites. Some 50–70% of a dose is excreted in the urine, about 20% as metabolites. It is eliminated both in the glomerular filtrate and by tubular secretion, and plasma concentrations are raised by probenecid. Parent drug and increased proportions of metabolites accumulate in renal failure. Elimination is increased through enhanced tubular secretion in patients with cystic fibrosis.
  • Side effects Phlebitis is common after intravenous injection. Its toxicity is otherwise similar to that of other penicillins. Clinical uses are those of the group 3 penicillins.
Dicloxacillin Preparation Products And Raw materials
Raw materials
Preparation Products
Dicloxacillin Suppliers
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Dicloxacillin Spectrum
3116-76-5, DicloxacillinRelated Search:
  • 有机
  • 双氯西林杂质
  • 有机化工原料
  • 医药原料
  • 青霉素类
  • C19H17Cl2N3O5S
  • C19H16CL2N3NaO5S
  • C19H17CL2N305S1
  • 双氯西林标准品
  • (2S,5R,6R)-3,3-二甲基-6-[5-甲基-3-(2,6-二氯苯基)-4-异噁唑甲酰氨基
  • 化合物 T21384
  • 二氯西林
  • (2S,5R,6R)-3,3-二甲基-6-[5-甲基-3-(2,6-二氯苯基)-4-异唑甲酰氨基]-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-甲酸
  • HEPTANE-4-CARBOXYLIC ACID 产品名称
  • (2S,5R,6R)-3,3-二甲基-6-[5-甲基-3-(2,6-二氯苯基)-4-异噁唑甲酰氨基]-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-甲酸
  • 双氯青霉素,双氯西林
  • 双氯西林
  • 双氯青霉素
  • 双氯苯唑青霉素
  • 3116-76-5
  • Dicloxacilline
  • Dicloxacilina
  • dicloxacilin
  • Dicloxacillinum
  • Dicloxacillin 13C4Q: What is Dicloxacillin 13C4 Q: What is the CAS Number of Dicloxacillin 13C4 Q: What are the applications of Dicloxacillin 13C4
  • DicloxacillinQ: What is Dicloxacillin Q: What is the CAS Number of Dicloxacillin Q: What is the storage condition of Dicloxacillin Q: What are the applications of Dicloxacillin
  • Dicloxacillin USP/EP/BP
  • DICLOXACILLIN MM(CRM STANDARD)
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo- (7CI, 8CI)
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[[3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-, [2S-(2α,5α,6β)]-
  • 3-(2,6-Dichlorophenyl)-5-methyl-4-isooxazolylpenicillin
  • [5-Methyl-3-(2,6-dichlorophenyl)-4-isoxazolylyl]penicillin
  • SODIUM DICLOXACILLIN
  • 4-Thia-1-azabicyclo3.2.0heptane-2-carboxylic acid, 6-3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolylcarbonylamino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
  • DICLOXACILLIN
  • 7-[[3-(2,6-dichlorophenyl)-5-methyl-oxazol-4-yl]carbonylamino]-3,3-dimethyl-6-oxo-2-thia-5-azabicyclo[3.2.0]heptane-4-carboxylic acid
  • 3-(2,6-DICHLOROPHENYL)-5-METHYL-4-ISOXAZOLYL PENICILLIN
  • methyldichlorophenylisoxazolylpenicillin
  • maclicine
  • dicloxacycline
  • Dichloxacillin
  • 7-[[3-(2,6-Dichlorophenyl)-5-methyl-oxazol-4-yl]carbonylamino]-3,3-dimethyl-6-oxo-2-thia-5-azabicyclo[3.2.0]
  • 6α-[[5-Methyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]carbonylamino]penicillanic acid
  • (2S,5R,6R)-6-[3-(2,6-Dichlorophenyl)-5-methylisoxazol-4-ylcarbonylamino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • Dicloxacillin (base and/or unspecified salts)
  • Staphcillin A
  • Stapenor D
  • R 13423
  • 6-[3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • brl1702
  • 6-dichlorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-6-(3-(
  • 6-(3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanicacid[qr
  • 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,6-(((3-(2,6-dichlorophenyl
  • 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxyl///
  • )-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3///

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