Cefoperazone sodium

Cefoperazone sodium Basic information
Product Name:Cefoperazone sodium
Synonyms:T-1551;sodiumcefoperazone;-tetrazol-5-yl)thio)methyl)-8-oxo-,monosodiumsalt,(6r-(6-alpha,7-beta(r*)));CEFAZONE;CEFOBID;CEFOBID SODIUM SALT;CEFOPERAZONE SODIUM;CEFOPERAZONE SODIUM SALT
CAS:62893-20-3
MF:C25H28N9NaO8S2
MW:669.66
EINECS:263-751-5
Product Categories:Chiral Reagents;Heterocycles;Penicillins and Cephalosporins (beta-Lactams);A - KAntibiotics;Antibacterial;Sulfur & Selenium Compounds;Intermediates & Fine Chemicals;Pharmaceuticals;Antibiotics A to;Antibiotics A-FAntibiotics;Chemical Structure Class;Mechanism of Action;Spectrum of Activity;Pharmaceutical intermediate;Interferes with Cell Wall SynthesisAntibiotics;VIIBRYD;BPC;APIs;62893-20-3
Mol File:62893-20-3.mol
Cefoperazone sodium Structure
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
color White to Off-White
Water Solubility Soluble in water. Slightly soluble in alcohol.
Merck 13,1943
BRN 4902135
Stability:Hygroscopic
InChIKeyNCFTXMQPRQZFMZ-WERGMSTESA-M
SMILESC(C1=C(CS[C@]2([H])[C@H](NC(=O)[C@@H](C3C=CC(O)=CC=3)NC(N3CCN(CC)C(=O)C3=O)=O)C(=O)N12)CSC1=NN=NN1C)(=O)O.[NaH] |&1:5,7,11,r|
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
MSDS Information
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
UsesFor studying the expression, binding, and inhibition of penicillin-binding proteins.Cefoperazone sodium salt is used in the study of drug-protein binding, expression and inhibition of penicillin-binding proteins during cell wall synthesis. It is as an antibacterial and antimicrobial agent useful for prevention of postoperative infection. It is used as an inhibitor of inactivation of alfa-antitrypsin.
DefinitionChEBI: Cefoperazone sodium is an organic molecular entity.
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
Biological Activitycefoperazone is a new semisynthetic cephalosporin with a broad spectrum of antibacterial activity. cefoperazone shows high activity against gram-positive bacteria and gram-negative bacilli, such as escherichia coli, klebsiella pneumoniae, and proteus species [1].
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).
in vitrothere was only a small spread between the minimum inhibitory concentrations and the minimum bactericidal concentrations of cefoperazone and a significant decrease in activity with an increase in inoculum size. cefoperazone is relatively stable to hydrolysis to β-lactamases produced by gram-negative bacteria. relative rates of hydrolysis of cefoperazone by cephalosporinases were 7.0 to 0.01[1]. in 50 strains of n. gonorrhoeae, the mic50 of cefoperazone was ≤ 0.004-0.06 μg/ml [2].
in vivoin four patients with cholelithiasis and one patient with carcinoma of the head of the pancreas, all of whom had normal renal functions, cefoperazone was intravenously administrated. in common duct bile, the maximum concentrations of cefoperazone ranged from 373.4 to 3,100 μg/ml while the concentrations ranged from 6.8 to 680 μg/ml in gall bladder bile. cefoperazone concentrations of the gall bladder wall ranged from 16.8 to 48.0 μg/g [3].
references[1] matsubara n, minami s, muraoka t, et al. in vitro antibacterial activity of cefoperazone (t-1551), a new semisynthetic cephalosporin[j]. antimicrobial agents and chemotherapy, 1979, 16(6): 731-735.
[2] baker c n, thornsberry c, jones r n. in vitro antimicrobial activity of cefoperazone, cefotaxime, moxalactam (ly127935), azlocillin, mezlocillin, and other beta-lactam antibiotics against neisseria gonorrhoeae and haemophilus influenzae, including beta-lactamase-producing strains[j]. antimicrobial agents and chemotherapy, 1980, 17(4): 757-761.
[3] nakamura t, hashimoto i, sawada y, et al. cefoperazone concentrations in bile and gall bladder wall after intravenous administration[j]. antimicrobial agents and chemotherapy, 1980, 18(6): 980-982.
Cefoperazone sodium Preparation Products And Raw materials
Raw materials{[(4-Ethyl-2,3-Dioxo-1-Piperazinyl) Carbonyl]Amino}-4-Hydroxy-Benzene Acetic Acid
Sodium alginate Sodium benzoate Sodium acetate Cefoperazone sodium +sulbactam sodium(1:1/2:1),Cefoperazone sodium/sullbactam sodium N-Aminoethylpiperazine sodium PYRAZOPHOS Trisodium phosphate Cefoperazone CARBONYL SULFIDE Cefoperazone sodium Diclofenac sodium 1,4-Dioxane Sodium citrate Sodium bicarbonate Sodium hydroxide Selenium dioxide CEFOPERAZONE SODIUM AND SULBACTAM SODIUM

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