Cefepime

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Cefepime
Cefepime2DCSD.svg
Cefepime ball-and-stick.png
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
Clinical data
Trade names Maxipime
AHFS/Drugs.com monograph
MedlinePlus a698021
Pregnancy cat. B1 (AU) B (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes Intravenous, intramuscular
Pharmacokinetic data
Bioavailability 100% (IM)
Metabolism Hepatic 15%
Half-life 2 hours
Excretion Renal 70–99%
Identifiers
CAS number 88040-23-7 YesY
ATC code J01DE01
PubChem CID 5479537
DrugBank DB01413
ChemSpider 4586395 YesY
UNII 807PW4VQE3 YesY
KEGG D02376 YesY
ChEBI CHEBI:478164 YesY
ChEMBL CHEMBL186 YesY
Chemical data
Formula C19H24N6O5S2 
Mol. mass 480.56 g/mol
 YesY (what is this?)  (verify)

Cefepime (INN, AAN, BAN, USAN) (/ˈsɛfɨpm/ or /ˈkɛfɨpm/) 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 organisms than third-generation agents. Cefepime hydrochloride was first marketed in 1994 and is currently marketed under various trade names, including Neopime (Neomed), Maxipime, Maxcef, Cepimax, Cepimex, and Axepim. A 2007 meta-analysis suggested when data of trials were combined, mortality was increased in patients treated with cefepime compared with other β-lactam antibiotics.[1] In response, the U.S. Food and Drug Administration performed their own meta-analysis which found no mortality difference.[2]

Clinical use[edit]

Main article: Cephalosporin

Cefepime is usually reserved to treat moderate to severe nosocomial pneumonia, infections caused by multiple drug-resistant microorganisms (e.g. Pseudomonas aeruginosa) and empirical treatment of febrile neutropenia.[3]

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.

Spectrum of bacterial susceptibility[edit]

Cefepime is a broad-spectrum cephalosporin antibiotic and has been used to treat bacteria responsible for causing pneumonia and infections of the skin and urinary tract. Some of these bacteria include Pseudomonas, Escherichia, and Streptoccus species. The following represents MIC susceptibility data for a few medically significant microorganisms.

  • Escherichia coli: ≤0.007 - 128 μg/ml
  • Pseudomonas aeruginosa: 0.06 - >256 μg/ml
  • Streptococcus pneumoniae: ≤0.007 - >8 μg/ml

[4]

Chemistry[edit]

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 increase the activity of cefepime against otherwise resistant organisms including Pseudomonas aeruginosa and Staphylococcus aureus.

References[edit]

  1. ^ 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:10.1016/S1473-3099(07)70109-3. PMID 17448937. 
  2. ^ "Information for Healthcare Professionals: Cefepime (marketed as Maxipime)". Retrieved 2009-08-02. 
  3. ^ 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. doi:10.1007/bf03256641. PMID 14720024. 
  4. ^ http://www.toku-e.com/Assets/MIC/Cefepime.pdf