Cefepime
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Cefepime
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| Systematic (IUPAC) name | |
| (6R,7R,Z)- 7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)- 3-((1-methylpyrrolidinium-1-yl)methyl)-8-oxo-5-thia- 1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate |
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| Identifiers | |
| CAS number | |
| ATC code | J01 |
| PubChem | |
| Chemical data | |
| Formula | C19H24N6O5S2 |
| Mol. mass | 480.56 g/mol |
| Pharmacokinetic data | |
| Bioavailability | 100% (IM) |
| Metabolism | Hepatic 15% |
| Half life | 2 hours |
| Excretion | Renal 70–99% |
| Therapeutic considerations | |
| Pregnancy cat. |
B1 (Au) |
| Legal status |
S4 (Au) |
| Routes | Intravenous, intramuscular |
Cefepime (INN) (pronounced /ˈsɛfəpiːm/, /ˈkɛfəpiːm/) is a fourth-generation cephalosporin antibiotic developed in 1994. Cefepime has an extended spectrum of activity against Gram-positive and Gram-negative bacteria, with greater activity against both Gram-negative and Gram-positive organisms than third-generation agents. Cefepime hydrochloride was first marketed in 1994 and is currently marketed under various trade names including Neopime(Neomed), Maxipime (Elan Pharma), Maxcef, Cepimax, Cepimex, and Axepim. A 2007 meta-analysis suggested that when data of trials were combined, mortality was increased in patients treated with cefepime compared with other antibiotics.[1] In response, the U.S. Food and Drug Administration issued an early communication about ongoing safety review that would take about four months to conduct.[2]
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[edit] Clinical use
Cefepime is usually reserved to treat severe nosocomial pneumonia, infections caused by multi-resistant microorganisms (e.g. Pseudomonas aeruginosa) and empirical treatment of febrile neutropenia.[3] The use of cefepime might become less common, since it has been associated to an increase mortality when used for different types of infections.
Cefepime has good activity against important pathogens including Pseudomonas aeruginosa, Staphylococcus aureus, and multiple drug resistant Streptococcus pneumoniae. A particular strength is its activity against Enterobacteriaceae. Whereas other cephalosporins are degraded by many plasmid- and chromosome-mediated beta-lactamases, cefepime is stable and is a front line agent when infection with Enterobacteriaceae is known or suspected.
[edit] Chemistry
The combination of the syn-configuration of the methoxyimino moiety and the aminothiazolyl moiety confers extra stability to β-lactamase enzymes produced by many bacteria. The N-methylpyrrolidine moiety increases penetration into Gram-negative bacteria. These factors increases the activity of cefepime against otherwise resistant organisms including Pseudomonas aeruginosa and Staphylococcus aureus.
[edit] References
- ^ Yahav D, Paul M, Fraser A, Sarid N, Leibovici L (2007). "Efficacy and safety of cefepime: a systematic review and meta-analysis". Lancet Infect Dis 7 (5): 338–48. doi:. PMID 17448937.
- ^ Early Communication About an Ongoing Safety Review: Cefepime (marketed as Maxipime). Retrieved on 2008-02-17.
- ^ Chapman TM, Perry CM (2003). "Cefepime: a review of its use in the management of hospitalized patients with pneumonia". Am J Respir Med 2 (1): 75–107. PMID 14720024.
[edit] External links
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