ChemicalBook > CAS DataBase List > Cefoperazone sodium

Cefoperazone sodium

Product Name
Cefoperazone sodium
CAS No.
62893-20-3
Chemical Name
Cefoperazone sodium
Synonyms
CEFOBID;T-1551;Dardum;Cefobis;Cefoneg;Farecef;Kefazon;Peracef;Perocef;Tomabef
CBNumber
CB5448988
Molecular Formula
C25H28N9NaO8S2
Formula Weight
669.66
MOL File
62893-20-3.mol
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Cefoperazone sodium Property

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
InChI
InChI=1/C25H27N9O8S2.Na.H/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2;;/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41);;/t15-,16-,22-;;/s3
InChIKey
NCFTXMQPRQZFMZ-WERGMSTESA-M
SMILES
C(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 Reference
62893-20-3(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
42/43
Safety Statements 
22-36/37
WGK Germany 
2
RTECS 
XI0374000
HS Code 
29419000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C4292
Product name
Cefoperazone sodium salt
Purity
870-1015 μg/mg (anhydrous basis)
Packaging
1g
Price
$83.7
Updated
2024/03/01
Sigma-Aldrich
Product number
C4292
Product name
Cefoperazone sodium salt
Purity
870-1015 μg/mg (anhydrous basis)
Packaging
5g
Price
$296
Updated
2024/03/01
Alfa Aesar
Product number
J65185
Product name
Cefoperazone sodium salt
Packaging
1g
Price
$65.65
Updated
2024/03/01
Alfa Aesar
Product number
J65185
Product name
Cefoperazone sodium salt
Packaging
5g
Price
$257
Updated
2024/03/01
Cayman Chemical
Product number
16113
Product name
Cefoperazone (sodium salt)
Purity
≥95%
Packaging
1g
Price
$49
Updated
2024/03/01
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Cefoperazone sodium Chemical Properties,Usage,Production

Description

Cefoperazone was synthesized by Toyama Chemicals Co. in 1978. Except for the hydroxyl group, the side chain attached to the cephem nucleus is the same as that of piperacillin. Cefoperazone shows excellent activity against gram-positive (except Staphylococcus) and gram- negative bacteria, including Pseudomonas aeruginosa. Its pharmacological characteristics are unique. Cefoperazone is excreted mainly in bile, and a concentration five to tenfold higher in bile than in serum is obtained. The transfer into cerebrospinal fluid is 10 – 30 % of the serum concentration; the half-life in serum is 2.0 – 2.6h, and the degree of binding with serum protein is as high as 86.6 %.

Chemical Properties

Faint beige powder

Originator

Cefobid,Pfizer,W. Germany,1981

Uses

Broad spectrum third generation cephalosporin antibiotic. An antibacterial.

Uses

antidepressant, serotonin reuptake inhibitor, 5HT1A agonist

Uses

For 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.

Definition

ChEBI: Cefoperazone sodium is an organic molecular entity.

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

Biological Activity

cefoperazone 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 Use

Cefoperazone 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 Treatments

Cefoperazone 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 vitro

there 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 vivo

in 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

Preparation Products

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View Lastest Price from Cefoperazone sodium manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Cefoperazone sodium 62893-20-3
Price
US $0.00-0.00/KG/Tin
Min. Order
1KG
Purity
870-1015 μg/mg; USP
Supply Ability
500KGS
Release date
2021-07-05
Sinoway Industrial co., ltd.
Product
Cefoperazone Sodium 62893-20-3
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20tons
Release date
2024-08-16
Hebei Weibang Biotechnology Co., Ltd
Product
Cefoperazone Sodium 62893-20-3
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-21

62893-20-3, Cefoperazone sodiumRelated Search:

Cefoperazone Sodium alginate Sodium acetate Trisodium phosphate CARBONYL SULFIDE Sodium benzoate Diclofenac sodium N-Aminoethylpiperazine Sodium citrate Selenium dioxide PYRAZOPHOS Sodium hydroxide Sodium bicarbonate 1,4-Dioxane (6R,7S)-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 open ring Impurities 7-Amino-3-(1,2,3-triazol-4-ylthio)methyl cephalosporanic acid 5-Desthiolyl-5-thioxo Cefoperazone

  • 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
  • CP-52640-2
  • BIOPERAZONE
  • 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-, monosodium salt, [6R-[6alpha,7beta(R*)]]-
  • Cefoperazone acid(sodium) CP2000,USP24,EP2001
  • CEFOPARAZONE SODIUM SALT
  • (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-carboxylicacid,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-,sodiuM salt (1:1), (6R,7R)-
  • Cefperazone Sodium
  • Cefoperazone Sodium, USP, Antibacterial.
  • Cefoperazone Sodium/Sulbactan Sodium
  • Cefazone sodium salt
  • CP-52640-2, T-1551, Bioperazone, Cefazone, Cefobid
  • CEFOPERAZONESODIUM,USP
  • 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-, monosodium salt, (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-, monosodium salt, [6R-[6α,7β(R*)]]-
  • Cefobine
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  • Cefosint
  • Dardum
  • Farecef
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  • Novobiocyl
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  • Perocef
  • Tomabef
  • [6R-[6alpha,7beta(R*)]]-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-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt
  • Cefoperazone Sodium Salt Standard
  • CAS 62983-20-3 Email/Skype:info@hbatun.com Whatsapp/Wechat:+86-13031440310
  • sodium,(6R,7R)-7-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  • Cefoperazone sodium USP/EP/BP
  • Cefoperazone sodium (sterile usp 30)
  • Sodium (6R,7R)-7-((R)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-2-(4-hydroxyphenyl)acetamido)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  • Cefoperazone sodiumQ: What is Cefoperazone sodium Q: What is the CAS Number of Cefoperazone sodium Q: What is the storage condition of Cefoperazone sodium Q: What are the applications of Cefoperazone sodium
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  • 62893-20-3
  • 62983-20-3
  • C25H26N9O8S2Na
  • C25H26N9NaO8S2
  • C25H26N5NaO8S2
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