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Cefoperazone

Cefoperazone Structure
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
Molecular Weight:
645.67
MOL File:
62893-19-0.mol
MSDS File:
SDS
Modify Date:
2024/4/25 13:42:50

Cefoperazone Properties

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
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)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
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

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.

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Cefoperazone Spectrum

(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 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 (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 Cefoperazone USP/EP/BP Cefoperazoner Cefoperazone acid, Pharma 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 Trolamine Impurity 5 62893-19-0 C25H27N9O8S2 Inhibitors Pharmaceutical