| Identification | More | [Name]
Cefoperazone sodium | [CAS]
62893-20-3 | [Synonyms]
BIOPERAZONE
CEFAZONE
CEFOBID
CEFOBID SODIUM SALT
CEFOPERAZONE SODIUM
CEFOPERAZONE SODIUM SALT
CP-52640-2
T-1551
sodiumcefoperazone
-tetrazol-5-yl)thio)methyl)-8-oxo-,monosodiumsalt,(6r-(6-alpha,7-beta(r*)))
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
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
Cefobis
Cefogram | [EINECS(EC#)]
263-751-5 | [Molecular Formula]
C25H26N9NaO8S2 | [MDL Number]
MFCD07793331 | [Molecular Weight]
667.65 | [MOL File]
62893-20-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Faint beige powder | [Melting point ]
200-202°C | [storage temp. ]
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. | [Usage]
An antibacterial | [Merck ]
13,1943 | [BRN ]
4902135 | [Stability:]
Hygroscopic | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R42/43:May cause sensitization by inhalation and skin contact . | [Safety Statements ]
S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
2
| [RTECS ]
XI0374000
| [HS Code ]
29419056 |
| Hazard Information | Back Directory | [Chemical Properties]
Faint beige powder | [Originator]
Cefobid,Pfizer,W. Germany,1981 | [Uses]
antidepressant, serotonin reuptake inhibitor, 5HT1A agonist | [Uses]
Broad spectrum third generation cephalosporin antibiotic. An antibacterial. | [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. |
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