Stereochemistry | ABSOLUTE |
Molecular Formula | C20H20N6O7S4 |
Molecular Weight | 584.669 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SCC(CSC3=NC(C)=C(CC(O)=O)S3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C4=CSC(N)=N4)C(O)=O
InChI
InChIKey=XDZKBRJLTGRPSS-BGZQYGJUSA-N
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
Cefodizime is a third-generation cephalosporin with a broad spectrum of antibacterial activity. Administered intravenously or intramuscularly 1 to 4 g of cefodizime daily for an average of 7 to 10 days produces a clinical cure in 80 to 100% of patients (adults, elderly or children) with upper or lower respiratory tract infections or urinary tract infections. 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. 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. Preliminary data from a small number of patients indicates 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 compared to 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. 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. Cefodizime targets penicillin-binding proteins (PBPs) 1A/B, 2, and 3 resulting in the eventual death of the bacterial cell. In vivo experimental models of infection showed that bacterial clearance by this drug is at least as effective compared with other 3rd generation cephalosporins. It has a similar adverse effect profile to other 3rd generation cephalosporins which is mainly being limited to gastrointestinal or dermatological side effects. It is not currently approved by the FDA for use in the United States.
Approval Year
Sample Use Guides
intravenously or intramuscularly, cefodizime 1 to 4 g daily for an average of 7 to 10 days
Route of Administration:
Other