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Cefoperazone

Cefoperazone
Cefoperazone structure
CAS No.
62893-19-0
Chemical Name:
Cefoperazone
Synonyms
Cefob;l~rdum;Medocef;CEFOPERAZONE;cefoperazine;Cephaperazon;Cefoperazoner;Perocef:Tomabef;Cefobis:Cefogram;CEFOPERAZONE ACID
CBNumber:
CB4752040
Molecular Formula:
C25H27N9O8S2
Formula Weight:
645.67
MOL File:
62893-19-0.mol

Cefoperazone Properties

Melting point:
169-171 C
Density 
1.77±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,2-8°C
pka
pKa 2.6 (Uncertain)
Merck 
14,1930
CAS DataBase Reference
62893-19-0(CAS DataBase Reference)
FDA UNII
7U75I1278D
SAFETY
  • Risk and Safety Statements
Hazard Codes  Xn
Risk Statements  20/21/22-36/37/38
Safety Statements  26-36
RTECS  XI0373900
HS Code  29419000

Cefoperazone Chemical Properties,Uses,Production

Description

Cefoperazone has a C-7 side chain reminiscent of piperacillin's and also possesses the C-3 side chain (MTT ) that often is associated with the bleeding and alcohol intolerance problems among patients taking cephalosporins. Its useful activity against pseudomonads partly compensates for this, although it is not potent enough to be used as a single agent against this difficult pathogen. The C-7 side chain does not convey sufficient resistance to many β-lactamases, although the addition of clavulanic acid or sulbactam would presumably help.

Chemical Properties

white crystals

Originator

Cefobid,Pfizer,W. Germany,1981

Uses

Antibacterial.

Uses

Cefoperazone also has a broad spectrum of antimicrobial action, including most clinically significant microorganisms: Gram-positive, Gram-negative, aerobic, and anaerobic. It is stable with respect to most beta-lactamases of Gram-positive and Gram-negative bacteria.
Cefoperazone is used for bacterial infections of the lower respiratory tract, urinary and sexual tracts, bones, joints, skin, soft tissues, abdominal, and gynecological infections. Synonyms of this drug are cefazon, cefobid, cefobis, and many others.

Definition

ChEBI: A semi-synthetic parenteral cephalosporin with a tetrazolyl moiety that confers beta-lactamase resistance.

Manufacturing Process

To 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 name

Cefobid (Pfizer).

Therapeutic Function

Antibiotic

Antimicrobial activity

A semisynthetic parenteral cephalosporin. It is unstable, losing activity on storage even at –20°C. A formulation with sulbactam is available in some countries.
It exhibits moderate activity against carbenicillin-sensitive strains of Ps. aeruginosa. Activity against Burk. cepacia and Sten. maltophilia is unreliable. It is much less stable to enterobacterial β-lactamases than most other cephalosporins of groups 4–6 and consequently has unreliable activity against many species, including β-lactamase-producing strains of H. influenzae and N. gonorrhoeae. It is active against Achromobacter, Flavobacterium, Aeromonas and associated non-fermenters. Past. multocida is extremely susceptible (MIC <0.01–0.02 mg/L). It exhibits modest activity against most Gram-negative anaerobes, but not B. fragilis. Sulbactam increases activity against many, but not all, enterobacteria and non-fermenters, and almost all B. fragilis.
A 2 g intravenous infusion achieves a peak plasma concentration of 250 mg/L. The plasma half-life is 1.5–2 h. Over 85% is bound to plasma proteins. It achieves therapeutic concentrations in tissue and inflammatory exudates. Variable low levels are found in the sputum up to 1.5% of simultaneous serum levels. Penetration into CSF is unreliable even in the presence of meningeal inflammation.
The bile is a major route of excretion, accounting for almost 20% of the dose. About 20–30% is eliminated in urine, almost entirely by glomerular filtration. Clearance is effectively unchanged by renal failure or dialysis.
Side effects associated with the methylthiotetrazole side chain have been reported. Diarrhea has been notable in some studies. Marked suppression of fecal flora, with the appearance of C. difficile, has occasionally been found. There is a 5–10% incidence of mild transient increases in liver function tests. Its potential toxicity and the availability of compounds with better β-lactamase stability and more reliable antipseudomonal activity have undermined its popularity.

Chemical Synthesis

Cefoperazone, (6R,7R)-7-[(R)-2-(4-ethyl-2,3-dioxo-1-piperazincarboxamido)-2-(p-hydroxyphenyl)acetamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo- 5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylic acid (32.1.2.84), is synthesized by acylating 7-amino-3-(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl-3-cefem-4-carboxylic acid (32.1.2.24) with a mixed anhydride synthesized from ethyl chloroformate and α-(4-ethylpiperazin-2, 3-dion-1-carbonylamino)-4-hydroxyphenylacetic acid (32.1.2.83), which in turn is synthesized from 4-ethylpiperazin-2,3-dion-1-carboxylic acid (32.1.1.29) and the sodium salt of 4-hydroxyphenylglycine.

Cefoperazone Preparation Products And Raw materials

Raw materials

Preparation Products


Cefoperazone Suppliers

Global( 229)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 21022 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8882 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29960 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
Hebei Guanlang Biotechnology Co., Ltd.
+8619930503282
sales3@crovellbio.com China 5460 58
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
sales@amoychem.com CHINA 6369 58
HubeiwidelychemicaltechnologyCo.,Ltd
18627774460
faith@widelychemical.com CHINA 743 58
BOC Sciences
1-631-485-4226
1-631-614-7828 inquiry@bocsci.com United States 19753 58
Chongqing Chemdad Co., Ltd
+86-13650506873
sales@chemdad.com CHINA 37282 58

View Lastest Price from Cefoperazone manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-07-02 cefoperazone sulbactam
62893-19-0
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
2021-07-01 Cefoperazone USP/EP/BP
62893-19-0
US $1.10 / g 1g 99.9% 100 Tons Min Dideu Industries Group Limited
2021-04-24 Cefoperazone
62893-19-0
US $10.00 / Kg/Bag 1KG 99% 100 mt Hebei Guanlang Biotechnology Co., Ltd.

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