Cefoperazone
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Cefoperazone
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CAS No:
62893-19-0
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Formula:
C25H27N9O8S2
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Chemical Name:
Cefoperazone
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Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,(6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino](4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,[6R-[6α,7β(R*)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2R)-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino](4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,(6R,7R)-;(6R,7R)-7-[[(2R)-2-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefoperazone;Cefoperazine;Cefobid;Cefob;Cephaperazon;Medocef;Cefozon;Biocefazon;72448-63-6
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CAS No:
Description
Cefoperazone is a cephalosporin antibiotic for inhibition of rMrp2-mediated [3H]E217βG uptake with IC50 of 199 μM.Target: AntibacterialCefoperazone is a sterile, semisynthetic, broad-spectrum, parenteral cephalosporin antibiotic for intravenous or intramuscular administration. After intravenous administration of 2 g of Cefoperazone, levels in serum rang from 202μg/mL to 375 μg/mL depending on the period of drug administration. After intramuscular injection of 2 g of Cefoperazone, the mea
Cefoperazone is a semi-synthetic parenteral cephalosporin with a tetrazolyl moiety that confers beta-lactamase resistance. It has a role as an antibacterial drug.|Cefoperazone is a semisynthetic broad-spectrum cephalosporin proposed to be effective against Pseudomonas infections. It is a third-generation antiobiotic agent and it is used in the treatment of various bacterial infections caused by susceptible organisms in the body, including respiratory tract infections, peritonitis, skin infections, endometritis, and bacterial septicemia. While its clinical use has been discontinued in the U.S., cefoperazone is available in several European countries most commonly under the product name, Sulperazon.|Cefoperazone is a Cephalosporin Antibacterial.|Cefoperazone is a semisynthetic, broad-spectrum, third-generation cephalosporin with antibacterial activity. Cefoperazone binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.|Semisynthetic broad-spectrum cephalosporin with a tetrazolyl moiety that is resistant to beta-lactamase. It may be used to treat Pseudomonas infections.
Cefoperazone Basic Attributes
645.67
645.67
263-749-4
7U75I1278D
DTXSID2022759
C61663
J - Antiinfectives for systemic use
29419000
Characteristics
271
-0.7
white crystalline powder
1.8±0.1 g/cm3
167-171 °C
1.819
239.1 Ų [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|244.1 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]
Safety Information
Ⅲ
2811
3
20/21/22-36/37/38
26-36
XI0373900
Xn
P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, P501
H317
|Danger|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 40 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H317 (98.04%): May cause an allergic skin reaction [Warning Sensitization, Skin]|Aggregated GHS information provided by 51 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting.
The degree of reversible protein binding varies with the serum concentration from 93% at 25 mcg/mL to 90% at 250 mcg/mL and 82% at 500 mcg/mL. Cefotetan is 88% plasma protein bound.
Drug Information
Indicated for the treatment of following infections caused by susceptible bacteria: 1) Respiratory tract infections caused by _S. pneumoniae_, _H. influenzae_, _S. aureus_ (penicillinase and non-penicillinase producing strains), _S. pyogenes_ (Group A beta-hemolytic streptococci), _P. aeruginosa_, _Klebsiella pneumoniae_, _E. coli_, _Proteus mirabilis_, and Enterobacter species. 2) Peritonitis and other intra-abdominal infections caused by _E. coli_, _P. aeruginosa_, and anaerobic gram-negative bacilli (including _Bacteroides fragilis_). 3) Bacterial septicemia caused by _S. pneumoniae_, _S. agalactiae_, _S. aureus_, _Pseudomonas aeruginosa_, _E. coli_, _Klebsiella_ spp., _Klebsiella pneumoniae_, Proteus species (indole-positive and indole-negative), _Clostridium_ spp. and anaerobic gram-positive cocci. 4) Infections of the skin and skin structures caused by S. aureus (penicillinase and non-penicillinase producing strains), S. pyogenes, and P. aeruginosa. 5) Pelvic Inflammatory Disease, Endometritis, and Other Infections of the Female Genital Tract caused by N. gonorrhoeae, S. epidermidis, S. agalactiae, E. coli, Clostridium spp., Bacteroides species (including Bacteroides fragilis), and anaerobic gram-positive cocci. 6) Urinary tract infections caused by Escherichia coli and Pseudomonas aeruginosa. 7) Enterococcal Infections. Although cefoperazone has been shown to be clinically effective in the treatment of infections caused by enterococci in cases of peritonitis and other intra-abdominal infections, infections of the skin and skin structures, pelvic inflammatory disease, endometritis and other infections of the female genital tract, and urinary tract infections, the majority of clinical isolates of enterococci tested are not susceptible to cefoperazone but fall just at or in the intermediate zone of susceptibility, and are moderately resistant to cefoperazone. However, _in vitro_ susceptibility testing may not correlate directly with _in vivo_ results. Despite this, cefoperazone therapy has resulted in clinical cures of enterococcal infections, chiefly in polymicrobial infections. Cefoperazone should be used in enterococcal infections with care and at doses that achieve satisfactory serum levels of cefoperazone.|FDA Label
Cefoperazone is a third generation cephalosporin antibiotic. Cefoperazone exerts its bactericidal effect by inhibiting the bacterial cell wall synthesis
Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)
Cefoperazone is excreted mainly in the bile.
No significant quanitity of metabolites have been identified in urine.
The mean serum half-life is approximately 2.0 hours, independent of the route of administration.
Like all beta-lactam antibiotics, cefoperazone binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.
Céfobis
Cefoperazone Use and Manufacturing
Method 1: Under nitrogen protection, 0°C and stirring, add 1-methyl-5-mercapto-1, 2, 3, 4-tetrazolium to the boron trifluoride monoethyl ether complex, and cool to- At 5°C, 7-ACA was added in batches and heated to 25°C for 2h. Add p-toluenesulfonic acid monohydrate at 15-20°C, then add 6mol/L hydrochloric acid dropwise, and stir at 20°C and 0-5°C for 1h. The crystals were collected by filtration and washed twice with acetonitrile-acetone to obtain compound (I) with a yield of 82%. Compound (I) was dissolved in dimethylacetamide (DMA), and trimethylchlorosilane was added dropwise under stirring at 10°C, and stirred at 25°C for 1 hour to obtain a solution of compound (I), which was directly used in the next reaction . Compound (II) was dissolved in DMA, and phosphorus oxychloride was added dropwise at -20°C and stirred for 2h. The above-mentioned compound (I) solution was dropped and stirred for 1 hour. The temperature was raised to 20°C, and sodium bicarbonate was added in batches to control the Ph value of the reaction liquid to 2. Add water and stir for 2h. Under vigorous stirring, the reaction solution was slowly poured into water. The solid was collected by filtration and recrystallized from acetonitrile-water to obtain white crystals of cefoperazone with a yield of 52.3% and a melting point of 169-171°C. [α]D23-35.5°. Using 7-ACA as a raw material, it firstly reacts with 5-mercapto-1-methyl-tetrazolium to form the 3-substituted 7-ATCA intermediate, and then with α-(p-hydroxyphenyl)-α-[(4- Ethyl-2, 3-dioxo-1-pyrazinyl)carboxamido]acetyl chloride is condensed, the Ph value is adjusted by acidification to crystallize the free acid of cefoperazone, which is dissolved with sodium bicarbonate to obtain cefoperazone The sodium salt. Method 2: Add 3.0g of 7-[(D)-2-amino-2-p-hydroxyphenylacetamido]-3-[[(1-methyl-1, 2, 3, 4-tetrazole-5 Mono)sulfur]methyl]cephem-4-carboxylic acid was suspended in 29 ml of water, and 0.95 g of anhydrous potassium carbonate was added. When the insoluble matter is completely dissolved, add 15ml ethyl acetate, and then add 1.35g 4-ethyl-2, 3-dioxopyrazinecarboxylic acid chloride within 15min at 0～5℃, and continue at 0～5℃ Reaction for 30min. After the completion of the reaction, 40 ml of ethyl acetate and 10 ml of acetone were added to the separated water layer and adjusted to Ph=2.0 with dilute hydrochloric acid. The organic layer was separated, washed twice with 10 ml of water, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was dissolved in 10 ml of acetone, and 60 ml of isopropanol was added to cause crystallization. The crystals were collected by filtration, washed with isopropanol, and dried to obtain 3.27 g of cefoperazone with a yield of 80.7% and a melting point of 188-190°C (decomposition).
It is a semi-synthetic broad-spectrum antibiotic with an antibacterial spectrum similar to cefotaxime
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals
Computed Properties
Molecular Weight:645.7
XLogP3:-0.7
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:13
Rotatable Bond Count:9
Exact Mass:645.14240120
Monoisotopic Mass:645.14240120
Topological Polar Surface Area:271
Heavy Atom Count:44
Complexity:1250
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Bactericidal effect achieved by inhibiting the biosynthesis of sensitive bacterial cell walls
Registered Holders
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Shandong Ruiying Pioneer Pharmaceutical Co., Ltd.
Active
China
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PAREKH CHEMICALS ITALIA SPA
Inactive
United States
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