Cefpodoxime

cefpodoxime
IUPAC name: see Chemistry Synonyms: cefpodoxime proxetil Formula: C15H17N5O6S2
Uses:	antibiotic drug
Properties:	cephalosporin beta-lactam
Hazards:	allergic reactions
Mass (g/mol): CAS #: 427.4554 82619-04-3

Cefpodoxime is a third-generation cephalosporin antibiotic useful against many Gram-postitive and Gram-negative bacteria, including enteric bacteria and other eubacteria. However, cefpodoxime cannot be used to treat Pseudomonas aeruginosa, Enterococcus, and Bacteroides fragilis. Cefpodoxime proxetil is an oral prodrug that becomes de-esterified into the cefpodoxime, the active metabolite.

Mechanism of action

Like other cephalosporins and peniciillins, cefpodoxime inhibits the proper formation of bacterial cells walls in the last stage of cell wall synthesis. Because cefpodoxime is stable against many beta-lactamases, many organisms that are resistant to penicillins and cephalosporins, due to their beta-lactamase production, may be susceptible to cefpodoxime. Some extended-spectrum beta-lactamases may inactivate cefpodoxime.

Chemistry

The systematic IUPAC chemical name for cefpodoxime is (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, and its chemical formula, C₁₅H₁₇N₅O₆S₂, gives is a molecular mass of 427.4554 g/mol. Like other cephalosporins and the penicillins, cefpodoxime contains a beta-lactam as the active functional group, subject to ring opening and irreversible binding via acylation to penicillin binding proteins 1A/1B.

Hazards

Patients with known allergies to penicillins or other cephalosporins should not take cefpodoxime, as this may result in a serious allergic reaction. Contact a physician immediately if any of the follow symptoms occur: hives, itching, skin rash, sore throat or mouth, swallowing or breathing difficulties, such as wheezing, or a vaginal infection. Take should be taken when using this drug in combination with anticoagulants.

Brand names

• Vantin®
• Banan®
• Doxef®
• Orelox®
• Otreon®
• Podomexef®

The most up-to-date information about Cefpodoxime and other drugs can be found at the following sites.

• Cefpodoxime - FDA approved drug information (drug label) from DailyMed (U.S. National Library of Medicine).
• Cefpodoxime - Drug information for consumers from MedlinePlus (U.S. National Library of Medicine).
• Cefpodoxime - Detailed information from DrugBank.