Cefuroxime
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| Category | Antibiotics |
| Catalog number | BBF-00751 |
| CAS | 55268-75-2 |
| Molecular Weight | 424.39 |
| Molecular Formula | C16H16N4O8S |
| Purity | 98% |
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Description
It is produced by the strain of Semisynthetic second generation cephalosporin. Cefuroxime is an orally active second-generation cephalosporin antibiotic with increased stability to β-lactamase. Cefuroxime has a broad spectrum activity against Gram-positive and Gram-negative bacteria.
Specification
| Related CAS | 56238-63-2 (sodium salt) |
| Synonyms | Cephuroxime; Cefuroxim; Cefuroximo; Cefuroximum; Sharox; Zinacef; Biofuroksym; Cefuril; (6R,7R)-7-(2-(2-Furyl)glyoxylamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid 7(sup 2)-(Z)-(O-methyloxime) carbamate (ester) |
| Storage | −20 °C under inert atmosphere |
| IUPAC Name | (6R,7R)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Canonical SMILES | CON=C(C1=CC=CO1)C(=O)NC2C3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O |
| InChI | InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1 |
| InChI Key | JFPVXVDWJQMJEE-IZRZKJBUSA-N |
Properties
| Appearance | White to Off-white Solid |
| Melting Point | 166-168 °C |
| Density | 1.76 g/cm3 (Predicted) |
| Solubility | Soluble in Phosphate Buffer; Slightly soluble in DMSO, Methanol |
Reference Reading
1. Cefuroxime axetil
W K Fant, M A Marx Drug Intell Clin Pharm . 1988 Sep;22(9):651-8. doi: 10.1177/106002808802200901.
Cefuroxime axetil is a orally active prodrug formulation of cefuroxime, which upon absorption undergoes immediate deesterification to free cefuroxime. Cefuroxime axetil offers an in vitro antibacterial spectrum against many gram-positive and some gram-negative organisms. Its beta-lactamase stability makes it useful in treating a variety of infections caused by beta-lactamase-producing strains of Haemophilus influenzae, Branhamella catarrhalis, and Staphylococcus aureus. Cefuroxime axetil has good activity against the Enterobacteriaceae and moderate activity against non-Bacteroides fragilis anaerobes. Clinical studies suggest it is at least as effective as ampicillin, amoxicillin, amoxicillin/clavulanic acid, penicillin V, or cefaclor in the treatment of uncomplicated urinary tract infections, acute otitis media, upper respiratory infections, skin and soft tissue infections, and uncomplicated gonorrhea.
2. Cefuroxime axetil in the treatment of sinusitis. A review
G E Pakes, A M Rauch, J J Collins, J A Graham Arch Fam Med . 1994 Feb;3(2):165-75. doi: 10.1001/archfami.3.2.165.
Cefuroxime axetil is a beta-lactamase-stable, second-generation, oral cephalosporin that penetrates sinus tissue in concentrations exceeding the MIC90 values (the minimum concentration of drug needed to inhibit the growth of 90% of an isolate of a particular microorganism) for pathogens most commonly associated with acute sinusitis, including Streptococcus pneumoniae and Haemophilus influenzae. A review of all clinical data published to date demonstrates that cefuroxime axetil has been evaluated in the treatment of acute sinusitis and acute exacerbations of chronic sinusitis ("acute-on-chronic sinusitis") in 18 clinical trials involving 1516 assessable patients. In 12 randomized, comparative trials, the rates of satisfactory clinical outcomes (cure or improvement, 79% to 100%) and bacteriologic eradication (84% to 100%) reported with the use of 250 mg of cefuroxime axetil twice daily were similar to those observed with the use of amoxicillin, amoxicillin/clavulanate potassium, cefaclor, cefadroxil, cefixime, clarithromycin, and doxycycline. In these comparisons, no antibiotic demonstrated any therapeutic advantages over cefuroxime axetil regarding time to symptom abatement. Cefuroxime axetil was at least as well tolerated as the other antibiotics. Overall, the role of cefuroxime axetil in the treatment of sinusitis appears to be as one of the broad-spectrum antibiotics that can be used for infections due to the most commonly implicated sinus pathogens, especially those due to the increasing number of relatively penicillin-resistant strains of S pneumoniae and beta-lactamase-producing strains of H influenzae and Moraxella catarrhalis.
3. Cefuroxime: antimicrobial activity, Pharmacology, and clinical efficacy
J L LeFrock, B R Smith Ther Drug Monit . 1983 Jun;5(2):149-60.
The antimicrobial activity, pharmacology, toxicity, and clinical efficacy of cefuroxime are reviewed. Cefuroxime has a second-generation cephalosporin spectrum of activity similar to cefamandole. Addition of a methoxyimino side chain has enhanced its beta-lactamase stability. Cefuroxime is active against certain cephalothin-, cefamandole-, and gentamicin-resistant bacteria. Cefuroxime has an extended half-life which allows dosing every 8 h. If penetrates into bodily tissues and fluids, including the cerebrospinal fluid, in therapeutic concentrations. Cefuroxime has been used successfully in the treatment of meningitis; sepsis; urinary tract, bone and joint, pulmonary, skin, and soft tissue infections; and gonorrhea. Competitive pricing of cefuroxime should provide a cost-effective substitute for cefamandole and, in certain situations, third-generation cephalosporins.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
