Ceftizoxime
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| Category | Antibiotics |
| Catalog number | BBF-00749 |
| CAS | 68401-81-0 |
| Molecular Weight | 383.41 |
| Molecular Formula | C13H13N5O5S2 |
| Purity | > 95% |
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Description
It is produced by the strain of Semisynthetic third generation cephalosporin for injection. Its sodium salt is used in preparations. Cefazide can be used for parenteral administration. Unlike other third-generation cephalosporins, the entire C-3 side chain of cefotaxime has been removed to prevent hydrolase inactivation. It is quite similar in nature to cefotaxime, but is not affected by metabolism.
Specification
| Related CAS | 68401-82-1 (sodium salt) |
| Synonyms | Ceftizoxima; Ceftizoximum; Cefizox; Epocelin; Eposerin; FK-749; FR 13749; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-, (6R-(6alpha,7beta(Z)))- |
| Storage | −20 °C under inert atmosphere |
| IUPAC Name | (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Canonical SMILES | CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=CCS3)C(=O)O |
| InChI | InChI=1S/C13H13N5O5S2/c1-23-17-7(5-4-25-13(14)15-5)9(19)16-8-10(20)18-6(12(21)22)2-3-24-11(8)18/h2,4,8,11H,3H2,1H3,(H2,14,15)(H,16,19)(H,21,22)/b17-7-/t8-,11-/m1/s1 |
| InChI Key | NNULBSISHYWZJU-LLKWHZGFSA-N |
Properties
| Appearance | Off-White to Pale Yellow Solid |
| Application | Anti-Bacterial Agents |
| Melting Point | > 224 °C (dec.) |
| Density | 1.89±0.1 g/cm3 (Predicted) |
| Solubility | Slightly soluble in Aqueous Base, DMSO (Heated), Methanol (Heated) |
Reference Reading
1. Is ceftizoxime an appropriate surrogate for amikacin in neonatal sepsis treatment? A randomized clinical trial
Peymaneh Alizadeh Taheri,Hossein Eslamieh,Peyman Salamati Acta Med Iran . 2011;49(8):499-503.
Neonatal sepsis, a life-threatening condition, presents with non-specific clinical manifestations and needs immediate empirical antimicrobial therapy. Choosing an appropriate antibiotic regimen covering the most probable pathogens is an important issue. In this study we compared the effectiveness of ceftizoxime and amikacin in the treatment of neonatal sepsis both in combination with ampicillin. In a randomized clinical trial, all term neonates with suspected sepsis referred to Bahrami hospital during March 2008 to March 2010 were evaluated. Patients were randomly recruited into two groups; one group receiving ampicillin and amikacin and the other ampicillin and ceftizoxime. Blood, urine and cerebrospinal fluid cultures, leukocyte count and C-reactive protein level were measured in all neonates. A total of 135 neonates were evaluated, 65 in amikacin group and 70 in ceftizoxime group. 60 neonates (85.7%) in ceftizoxime group and 54 neonates (83.1%) in amikacin group responded to the treatment (P= 0.673 and χ2 = 0.178). Only 24 (18%) blood samples had a report of positive blood culture. The most frequent pathogen was coagulase negative staphylococcus with the frequency of 58.32% of all positive blood samples. Ceftizoxime in combination with ampicillin is an appropriate antimicrobial regimen for surrogating the combination of ampicillin and amikacin to prevent bacterial resistance against them.
2. Ceftizoxime disposition in neonates and infants during the first six months of life
M D Reed,T S Yamashita,J Tanaka-Kido,S D Minton,J L Blumer,J I Santos,W M Gooch 3rd DICP . 1991 Apr;25(4):344-7. doi: 10.1177/106002809102500401.
The single-dose pharmacokinetics of ceftizoxime sodium were studied in 52 neonates and infants between 0.1 and 189 days of age. Subjects received ceftizoxime 25 or 50 mg/kg iv over 15-30 minutes. The drug was administered q8-12h for five days to permit tolerance evaluation on repetitive dosing. No differences were observed in ceftizoxime pharmacokinetic parameter estimates relative to dose. However, marked differences were observed in ceftizoxime pharmacokinetic characteristics relative to infant age; ceftizoxime half-life and mean residence time decreased, whereas body clearance increased with infant age. Ceftizoxime volume of distribution remained relatively constant over infant age. No adverse effects associated with ceftizoxime administration were observed. These data suggest that ceftizoxime 50 mg/kg q12h be used for infants less than or equal to 2 weeks of age (less than or equal to 40 weeks postconceptional age) and that 50 mg/kg q8h be administered for older infants.
3. An update on the in vitro activity of ceftizoxime and other cephalosporin/cephamycin antimicrobial agents against clinically significant anaerobic bacteria
K E Aldridge Clin Ther . 1990;12 Suppl C:3-12.
The in vitro activity of certain beta-lactam agents against aerobic and anaerobic bacteria is influenced by the method and medium used for susceptibility testing. The in vitro activity of ceftizoxime and cefoxitin against Bacteroides fragilis group strains varies when either the broth microdilution or agar dilution method is used. In general, minimal inhibitory concentration values from broth microdilution are two- to fourfold lower than those from agar dilution. Broth microdilution test results with ceftizoxime have recently been shown to correlate more closely with clinical outcome in patients than those from agar dilution testing. Broth microdilution has become the recommended method of the National Committee for Clinical Laboratory Standards for testing ceftizoxime. Using broth microdilution testing, the in vitro activity of ceftizoxime has been shown to be as good as or better than that of cefoxitin, cefotetan, and cefotaxime against anaerobes, including the B fragilis group. Ceftizoxime also had good activity against B fragilis group strains resistant to cefoxitin or cefotetan. Time-kill kinetic studies have shown that the bactericidal activity of ceftizoxime is equal to or greater than that of cefoxitin or cefotetan against both cefoxitin-susceptible or cefoxitin-resistant strains of the B fragilis group.
4. Cefpodoxime proxetil
Abdullah A Al-Badr,Gamal A E Mostafa,Yazeed H Al-Otaibi Profiles Drug Subst Excip Relat Methodol . 2019;44:1-165. doi: 10.1016/bs.podrm.2019.02.001.
A comprehensive profile of cefpodoxime proxetil including the nomenclatures, formulae, elemental composition, appearance, uses, and applications. The methods which were developed for the preparation of the drug substance and their respective schemes are outlined. The physical characteristics of the drug including the ionization constant, solubility, X-ray powder diffraction pattern, differential scanning calorimetry, thermal behavior, and spectroscopic studies are included. The methods which were used for the analysis of the drug substance in bulk drug and/or in pharmaceutical formulations includes the compendial, spectrophotometric, electrochemical and the chromatographic methods. The other studies which was carried out on this drug substance are including the drug stability, pharmacokinetics, bioavailability, drug evaluation, comparison and several compiled reviews. Finally, more than two hundred references are listed at the end of this profile.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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