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Cefoperazone sodium

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Cefoperazone sodium Basic information
Cefoperazone sodium Chemical Properties
  • Melting point:200-202°C
  • storage temp. Inert atmosphere,2-8°C
  • solubility H2O: 50 mg/mL, clear, faintly yellow
  • form powder
  • Water Solubility Soluble in water. Slightly soluble in alcohol.
  • Merck 13,1943
  • BRN 4902135
  • CAS DataBase Reference62893-20-3(CAS DataBase Reference)
Safety Information
  • Hazard Codes Xn
  • Risk Statements 42/43
  • Safety Statements 22-36/37
  • WGK Germany 2
  • RTECS XI0374000
  • HS Code 29419000
Cefoperazone sodium Usage And Synthesis
  • Chemical PropertiesFaint beige powder
  • OriginatorCefobid,Pfizer,W. Germany,1981
  • UsesBroad spectrum third generation cephalosporin antibiotic. An antibacterial.
  • Usesantidepressant, serotonin reuptake inhibitor, 5HT1A agonist
  • Manufacturing ProcessTo a suspension of 3.0 g of 7-[D-(-)-α-amino-p-hydroxyphenylacetamido]-3- [5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-?3-cephem-4-carboxylic acid in 29 ml of water was added 0.95 g of anhydrous potassium carbonate. After the solution was formed, 15 ml of ethyl acetate was added to the solution, and 1.35 g of 4-ethyl-2,3-dioxo-1-piperazinocarbonyl chloride was added to the resulting solution at 0°C to 5°C over a period of 15 minutes, and then the mixture was reacted at 0°C to 5°C for 30 minutes. After the reaction, an aqueous layer was separated off, 40 ml of ethyl acetate and 10 ml of acetone were added to the aqueous layer, and then the resulting solution was adjusted to a pH of 2.0 by addition of dilute hydrochloric acid. Thereafter, an organic layer was separated off, the organic layer was washed two times with 10 ml of water, dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was dissolved in 10 ml of acetone, and 60 ml of 2-propanol was added to the solution to deposit crystals. The deposited crystals were collected by filtration, washed with 2- propanol, and then dried to obtain 3.27 g of 7-[D-(-)-α-(4-ethyl-2,3-dioxo)-1- piperazinocarbonylamino)-p-hydroxyphenylacetamido]-3-[5-(1-methyl- 1,2,3,4-tetrazolyl)thiomethyl]-?3-cephem-4-carboxylicacid, yield 80.7%. The product forms crystals, MP 188°C to 190°C (with decomposition).
  • brand nameCefobid (Pfizer).
  • Therapeutic FunctionAntibiotic
  • Clinical UseCefoperazone sodium is a third-generation, antipseudomonalcephalosporin that resembles piperacillinchemically and microbiologically. It is active against manystrains of P. aeruginosa, indole-positive Proteus spp.,Enterobacter spp., and S. marcescens that are resistant tocefamandole. It is less active than cephalothin againstGram-positive bacteria and less active than cefamandoleagainst most of the Enterobacteriaceae. Like piperacillin,cefoperazone is hydrolyzed by many of the β-lactamasesthat hydrolyze penicillins. Unlike piperacillin, however, itis resistant to some (but not all) of the β-lactamases thathydrolyze cephalosporins.Cefoperazone is excreted primarily in the bile. Hepaticdysfunction can affect its clearance from the body. 
  • Veterinary Drugs and TreatmentsCefoperazone is used to treat serious infections, particularly susceptible Enterobacteriaceae not susceptible to other less expensive agents or when aminoglycosides are not indicated (due to their potential toxicity).
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