| Identification | More | [Name]
Cefuroxime sodium | [CAS]
56238-63-2 | [Synonyms]
CEFUROXIME NA
CEFUROXIME SODIUM
CEFUROXIME SODIUM SALT
sodium [6r-[6a,7b(z)]]-3-[[(aminocarbonyl)oxy]methyl]-7-[2-furyl(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
7-beta(z)))-6-alph
ethyl)-7-((2-furanyl(methoxyimino)acetyl)amino)-8-oxo-,monosodiumsalt,(6r-(
sodiumcefuroxime
zinacef
sodium [6R-[6alpha,7beta(Z)]]-3-[[(aminocarbonyl)oxy]methyl]-7-[2-furyl(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Cefuroxime Sodium(sterile)
Cefroxine
CEFUROXIME SODIUM/ CEFUROXIME
(6R,7R)-3-[[(Aminocarbonyl)oxy]methyl]-7-[[(2Z)-2-furanyl(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Sodium Salt
Anaptivan
Biociclin
Biofurex
Cefurin
Duxima
Novocef
Zinace | [EINECS(EC#)]
260-073-1 | [Molecular Formula]
C16H16N4NaO8S | [MDL Number]
MFCD00079036 | [Molecular Weight]
447.38 | [MOL File]
56238-63-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
240-245°C(dec) | [alpha ]
D20 +60° (c = 0.91 in water) | [storage temp. ]
2-8°C
| [solubility ]
Freely soluble in water, very slightly soluble in ethanol (96 per cent). | [form ]
neat | [pka]
pKa (water): 2.5; (DMF): 5.1(at 25℃) | [color ]
White to Pale Beige | [Water Solubility ]
Freely soluble in water | [Usage]
Antibacterial | [InChIKey]
URDOHUPGIOGTKV-JTBFTWTJSA-M | [CAS DataBase Reference]
56238-63-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R42/43:May cause sensitization by inhalation and skin contact .
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
2
| [RTECS ]
XI0330000
| [HS Code ]
29419090 |
| Questions And Answer | Back Directory | [Description]
Cefuroxime sodium is marketed by Eli Lilly and Company under the trade name of Kefurox® and by Glaxo Limited under the trade name of Zinacef®. Cefuroxime sodium is an off-white to white amorphous powder. Cefuroxime sodium is an injectable second generation, semisynthetic, broad spectrum cephalosporin antibiotic with excellent activity in vitro, enhanced stability to many enterobacterial β-lactamases and favorable pharmacokinetic properties.
It is used to treat a wide variety of bacterial infections. It is effective for treating meningitis, lower respiratory tract infections, urinary tract infections, gonorrhea, septicemia, skin and skin infections, bone and joint infections, and is approved for surgical prophylaxis.
| [References]
[1] Timothy J. Woznaik and John R. Hicks, Analytical Profile of Cefuroxime Sodium, Analytical Profiles of Drug Substances, 1991, vol. 20, 209-236
[2] https://dailymed.nlm.nih.gov
[3] L. M. Galanti, J. D. Hecq, D. Vanbeckbergen and J. Jamart, Long-term stability of cefuroxime and cefazolin sodium in intravenous infusions, Journal of Clinical Pharmacy and Therapeutics, 1996, vol. 21, 185-189
|
| Hazard Information | Back Directory | [Chemical Properties]
White Crystalline Solid | [Originator]
Ultroxim,Duncan,Italy,1978 | [Uses]
Cephalosporin antibacterial. | [Definition]
ChEBI: Cefuroxime sodium is an organic molecular entity. | [Manufacturing Process]
A stirred mixture of N,N-dimethylacetamide (75 ml), acetonitrile (75 ml),
triethylamine (42 ml, 0.3 mol) and (6R,7R)-7-amino-3-carbamoyloxy-methylceph-3-em-4-carboxylic acid was immersed in an ice-bath and water
(10 ml) was added. The mixture was stirred at 0°C to 2°C for 45 minutes, the
solid slowly dissolving to give a yellow solution.
Meanwhile a stirred suspension of phosphorus pentachloride (14.99 g, 0.072
mol) in dry dichloromethane (150 ml) was cooled to 0°C, and N,N-dimethylacetamide (27.5 ml) was added. The resulting solution was recooled
to -10°C and 2-(fur-2-yl)-2-methoxyiminoacetic acid (synisomer) (12.17 g,
0.072 mol) was added. The mixture was stirred at -10°C for 15 minutes and
crushed ice (35 g) was added. The mixture was stirred at 0°C for 10minutes,
where after the lower dichloromethane phase was added over 10 minutes to
the cephalosporin solution prepared above, cooled to -10°C so that the
reaction temperature rose steadily to 0°C. The mixture was stirred at 0°C to
2°C for 1 hour, where after the cooling bath was removed and the reaction
temperature allowed to rise to 20°C over 1 hour. The reaction mixture was
then added slowly to 2 N hydrochloric acid (100 ml) diluted with cold water
(1.15 l) at 5°C. The pH of the two phase mixture was adjusted to below 2
with 2 N hydrochloric acid (10 ml), and the mixture was stirred and recooled
to 5°C. The solid which precipitated was filtered, washed with
dichloromethane (100 ml) and water (250 ml), and dried in vacuo at 40°C
overnight to give the title compound (22.04 g, 86.6%). | [Brand name]
Kefurox (Lilly); Zinacef
(GlaxoSmithKline). | [Therapeutic Function]
Antibiotic | [Clinical Use]
Cefuroxime (Zinacef) is the first of a series of α-methoximinoacyl–substituted cephalosporins that constitute most of thethird-generation agents available for clinical use. A syn alkoximinosubstituent is associated with β-lactamase stability in these cephalosporins.78 Cefuroxime is classified as a secondgenerationcephalosporin because its spectrum of antibacterialactivity more closely resembles that of cefamandole. It is,however, active against β-lactamase–producing strains thatare resistant to cefamandole, such as E. coli, K. pneumoniae,N. gonorrhoeae, and H. influenzae. Other important Gramnegativepathogens, such as Serratia, indole-positive Proteusspp., P. aeruginosa, and B. fragilis, are resistant.Cefuroxime is distributed throughout the body. It penetratesinflamed meninges in high enough concentrations tobe effective in meningitis caused by susceptible organisms.Three-times-daily dosing is required to maintain effectiveplasma levels for most sensitive organisms, such asNeisseria meningitidis, Streptococcus pneumoniae, and H.influenzae. It has a plasma half-life of 1.4 hours. | [storage]
Store at -20°C |
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