Cefoperazone

Product Name: Cefoperazone
CAS No.: 62893-19-0
Chemical Name: Cefoperazone
Synonyms: CEFOPERAZONE ACID;Cefoperazone (Cefobid);(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-carboxylic acid;Cefob;l~rdum;Medocef;CEFOPERAZONE;cefoperazine;Cephaperazon;Cefoperazoner
CBNumber: CB4752040
Molecular Formula: C25H27N9O8S2
Formula Weight: 645.67
MOL File: 62893-19-0.mol

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Cefoperazone Property

Melting point:: 169-171 C
Density: 1.77±0.1 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMSO (Slightly, Sonicated), Methanol (Slightly, Heated, Sonicated)
form: Solid
pka: pKa 2.6 (Uncertain)
color: White to Off-White
Merck: 14,1930
InChI: InChI=1S/C25H27N9O8S2/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-/m1/s1
InChIKey: GCFBRXLSHGKWDP-XCGNWRKASA-N
SMILES: N12[C@@]([H])([C@H](NC([C@H](NC(N3CCN(CC)C(=O)C3=O)=O)C3=CC=C(O)C=C3)=O)C1=O)SCC(CSC1N(C)N=NN=1)=C2C(O)=O
CAS DataBase Reference: 62893-19-0(CAS DataBase Reference)

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Safety

Hazard Codes: Xn
Risk Statements: 20/21/22-36/37/38
Safety Statements: 26-36
RTECS: XI0373900
HS Code: 29419000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: C242903
Product name: CefoperazoneAcid
Packaging: 25g
Price: $365
Updated: 2021/12/16

Chem-Impex

Product number: 38390
Product name: Cefoperazone,98%(HPLC)
Purity: 98%(HPLC)
Packaging: 25G
Price: $464.8
Updated: 2021/12/16

ChemScene

Product number: CS-2155
Product name: Cefoperazone
Purity: 99.82%
Packaging: 5g
Price: $199
Updated: 2021/12/16

ChemScene

Product number: CS-2155
Product name: Cefoperazone
Purity: 99.82%
Packaging: 500mg
Price: $50
Updated: 2021/12/16

AK Scientific

Product number: J10932
Product name: Cefoperazone
Packaging: 25mg
Price: $57.2
Updated: 2021/12/16

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Cefoperazone Chemical Properties,Usage,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.

Uses

Cefoperazone acid is an antimicrobial β-lactamase inhibitor.

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.

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 |á-(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.

References

[1]. kato y1,takahara s,kato s,kubo y,sai y,tamai i,yabuuchi h,tsuji a. involvement of multidrug resistance-associated protein 2 (abcc2) in molecular weight-dependent biliary excretion of beta-lactam antibiotics.drug metab dispos.2008 jun;36(6):1088-96. doi: 10.1124/dmd.107.019125. epub 2008 mar 13.
[2]. craig wa,gerber au. pharmacokinetics of cefoperazone: a review. drugs.1981;22suppl 1:35-45.

Cefoperazone Preparation Products And Raw materials

Raw materials

1-Phenyltetrazole-5-thiol Acetaminophen Pyrazine Nitrogen Acetone p-Toluenesulfonic acid monohydrate Tetrazole Chlorotrimethylsilane Acid chloride 5-Mercapto-1-methyltetrazole N,N-Dimethylacetamide (2S)-1-(3-Acetylthio-2-methyl-1-oxopropyl)-L-proline

Preparation Products

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View Lastest Price from Cefoperazone manufacturers

Hebei Weibang Biotechnology Co., Ltd

Product: Cefoperazone 62893-19-0
Price: US $10.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 100 mt
Release date: 2024-11-13

Shaanxi TNJONE Pharmaceutical Co., Ltd

Product: Cefoperazone 62893-19-0
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20tons
Release date: 2024-04-08

Hebei Mojin Biotechnology Co., Ltd

Product: Cefoperazone 62893-19-0
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2023-07-03

62893-19-0, CefoperazoneRelated Search:

7-TMCA (2R)-2-[(4-Ethyl-2,3-dioxopiperazinyl)carbonylamino]-2-(4-hydroxyphenyl)acetic acid 4-Ethyl-2,3-dioxo-1-piperazine carbonyl chloride Cefoperazone sodium +sulbactam sodium(1:1/2:1),Cefoperazone sodium/sullbactam sodium CEFADROXIL Cefoperazone SALOR-INT L169811-1EA 1-Ethyl-2,3-dioxopiperazine Cephalexin 7-Phenyl-acetamido-deacetoxy-cephalosporanic-acid Cefadroxil Cefoperazone acid(sodium) CP2000,USP24,EP2001,CEFOPERAZONE SODIUM,CEFOPERAZONE SODIUM SALT sodium [6R-[6alpha,7beta(R*)]]-7-(aminophenylacetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate BENZENEACETAMIDE, N-(2-AMINOETHYL)-4-HYDROXY- Sulbactam sodium·cefoperazone sodium,Cefoperazone sodium·sulbactam sodium PIPERAZINE-2,3-DIONE CEFOPERAZONE SODIUM FOR INJECTION Cefoperazone dihydrate

(6R,7R)-7-{[(2S)-2-{[(4-ETHYL-2,3-DIOXO-1-PIPERAZINYL)CARBONYL]AMINO}-2-(4-HYDROXYPHENYL)ACETYL]AMINO}-3-{[(1-METHYL-1H-TETRAZOL-5-YL)SULFANYL]METHYL}-8-OXO-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBO XYLIC ACID

CEFOPERAZONE

CEFOPERAZONE ACID

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-,(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 (Cefobid)

(6r-(6-alpha,7-beta(r*)))--tetrazol-5-yl)thio)methyl)-8-oxo

-1-piperazinyl)carbonyl)amino)(4-hydroxyphenyl)acetyl)amino)-3-(((1-methyl-1h

cefoperazine

Cefobis：Cefogram

l~rdum

Perocef：Tomabef

Cefoperazone Dihydrate (200 mg)

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)-

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*)]]-

Cefob

Cephaperazon

Medocef

Cefoperazone (base and/or unspecified salts)

Cefoperazone SodiuM IMp. B

Cefoperazone free acid

[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

(6S,7S)-7-[[2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)-oxomethyl]amino]-2-(4-hydroxyphenyl)-1-oxoethyl]amino]-3-[[(1-methyl-5-tetrazolyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic

Cefoperazone dihydrate CRS

(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-carboxylic acid

Cefoperazone USP/EP/BP

Cefoperazoner

Cefoperazone acid, Pharma

Trolamine Impurity 5

Cefoperazone in methanol

62893-19-0

C25H27N9O8S2

Inhibitors

Pharmaceutical