Cefodizime
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| Category | Antibiotics |
| Catalog number | BBF-00726 |
| CAS | 69739-16-8 |
| Molecular Weight | 584.67 |
| Molecular Formula | C20H20N6O7S4 |
| Purity | > 95% |
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Description
It is produced by the strain of Semisynthetic third generation cephalosporin for injection. Cefodizime has broad-spectrum antibacterial activity against aerobic gram positive and gram negative bacteria. Clinically, it has been shown to be effective against upper and lower respiratory tract infections, urinary tract infections, and gonorrhea. Cefodizime is a bactericidal antibiotic that targets penicillin-binding proteins (PBPs) 1A/B, 2, and 3 resulting in the eventual death of the bacterial cell. It also has immunomodulatory effect.
Specification
| Related CAS | 86329-79-5 (sodium salt) |
| Synonyms | Cefodizima; Cefodizimum; CDZM; 7-(α-(Z)-Methoxyimino-α-(2-aminothiazol-4-yl)acetamido)-3-((5-carboxymethyl-4-methylthiazol-2-yl)thiomethyl)-3-cephem-4-carboxylic Acid |
| Storage | −20 °C |
| IUPAC Name | (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Canonical SMILES | CC1=C(SC(=N1)SCC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)O)CC(=O)O |
| InChI | InChI=1S/C20H20N6O7S4/c1-7-10(3-11(27)28)37-20(22-7)36-5-8-4-34-17-13(16(30)26(17)14(8)18(31)32)24-15(29)12(25-33-2)9-6-35-19(21)23-9/h6,13,17H,3-5H2,1-2H3,(H2,21,23)(H,24,29)(H,27,28)(H,31,32)/b25-12-/t13-,17-/m1/s1 |
| InChI Key | XDZKBRJLTGRPSS-BGZQYGJUSA-N |
Properties
| Appearance | White to Yellowish Crystalline Powder |
| Melting Point | > 170 °C (dec.) |
| Density | 1.86±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Water; DMSO, Methanol (Heated); Almost insoluble in Ethanol, Ether |
Reference Reading
1. Cefodizime. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use
L B Barradell, R N Brogden Drugs. 1992 Nov;44(5):800-34. doi: 10.2165/00003495-199244050-00008.
Cefodizime is a third generation cephalosporin with a broad spectrum of antibacterial activity. Administered intravenously or intramuscularly, cefodizime 1 to 4 g daily for an average of 7 to 10 days produced clinical cure in 80 to 100% of patients (adults, elderly or children) with upper or lower respiratory tract infections or urinary tract infections, and in comparative trials cefodizime was as effective as other third generation cephalosporins. A single dose of cefodizime 1 or 2 g is also useful in treating lower urinary tract infections, particularly uncomplicated infections, with a rate of clinical success of 72 to 88%. Urogenital gonorrhoea, whether caused by beta-lactamase producing or non-beta-lactamase producing Neisseria gonorrhoeae, is very effectively treated by single dose therapy with intramuscular cefodizime 0.25 to 1 g (virtually 100% cured). Preliminary data from a small number of patients indicate that cefodizime may also be useful in the treatment of otitis media, sinusitis and gynaecological infections, and for the prophylaxis or treatment of surgical infections. The clinical efficacy of cefodizime in comparison with other third generation cephalosporins is superior to that predicted from in vitro results. This superior activity of cefodizime may be related to the relatively long elimination half-life of the drug or its ability to modify some functions of the immune system--a potentially important finding awaiting further investigation. Cefodizime is well tolerated and has a tolerability profile similar to other members of its class with systemic adverse events being primarily gastrointestinal or dermatological. Thus, limited comparative studies indicate cefodizime has the potential to become a useful alternative to current antimicrobial therapy for the treatment of a variety of infections. Cefodizime may be more convenient to administer than some other agents of its class as it may be given once or twice daily. While there are no trials comparing cefodizime to other third generation cephalosporins in immunosuppressed populations, preliminary information indicates cefodizime may be useful in this group.
2. Safety profile of cefodizime
K Andrassy Infection. 1992;20 Suppl 1:S36-40. doi: 10.1007/BF01709949.
The results of animal toxicology studies with cefodizime (CDZ) showed no reason for concern with respect to drug safety. Renal tolerance of CDZ proved to be better than that observed with other cephalosporins; furthermore, CDZ had no adverse effects on spermatogenesis, fertility or embryonic development. A total of 6,299 patients were treated with CDZ in clinical trials worldwide, while 1,225 patients received cefuroxime, cefotaxime, cefmenoxime or cefizoxime in comparative studies. The incidence of mortality in the repeated dose trials was 1.6% (CDZ) and 1.75% (comparators); the incidence of adverse drug reactions (ADRs) was 3.06% and 3.64%, respectively. ADRs were mostly of gastrointestinal or allergic nature. In no case was a causative relationship established between CDZ and the death of a patient. Any influence of CDZ on platelet count and function, plasma coagulation and vitamin K metabolism has been excluded. Cefodizime has a favorable risk/benefit ratio.
3. In vitro activity of cefodizime
H Knothe, P M Shah Infection. 1992;20 Suppl 1:S3-8. doi: 10.1007/BF01709942.
Cefodizime is a bactericidal cephem with the typical broad spectrum activity of an aminothiazolyl cephalosporin, including both gram-positive and gram-negative bacteria: its MIC90 is 0.125 mg/l for Streptococcus pneumoniae, Streptococcus pyogenes and other streptococci; and 0.05 mg/l for Haemophilus spp., Neisseria meningitidis, Neisseria gonorrhoeae and Moraxella catarrhalis; while beta-lactamase positive strains of M. catarrhalis require 1 mg/l. Less than 1 mg/l is needed for Escherichia coli, Klebsiella spp., Proteus spp. and Shigella spp. The MIC90 is 4 mg/l for methicillin-sensitive Staphylococcus aureus, Morganella morganii, Providencia spp. and most strains of Serratia marcescens, Citrobacter spp. and Enterobacter spp. Staphylococcus epidermidis, Enterococcus faecalis and most strains of Pseudomonas spp. and Acinetobacter spp. are considered cefodizime-resistant. Cefodizime is unaffected by plasmid-mediated beta-lactamases, but it is hydrolyzed by some chromosomally mediated enzymes, thus resembling other third-generation cephalosporins. Cefodizime has high affinity for PBP 3 and PBP IA and IB (Escherichia coli); in S. aureus it shows the highest affinity for PBP 1.
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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 ╳
