Cefepime

Cefepime
Clinical data
Pronunciation/ˈsɛfɪpiːm/ or /ˈkɛfɪpiːm/
Trade namesMaxipime, Voco
AHFS/Drugs.comMonograph
MedlinePlusa698021
License data
Pregnancy
category
  • AU: B1
Routes of
administration		Intravenous, intramuscular
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability100% (IM)
MetabolismHepatic 15%
Elimination half-life2 hours
ExcretionRenal 70–99%
Identifiers
  • (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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.171.025 Edit this at Wikidata
Chemical and physical data
FormulaC19H24N6O5S2
Molar mass480.56 g·mol−1
3D model (JSmol)
Melting point150 °C (302 °F) (dec.)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)/c3nc(sc3)N)C[N+]4(C)CCCC4)C([O-])=O
  • InChI=1S/C19H24N6O5S2/c1-25(5-3-4-6-25)7-10-8-31-17-13(16(27)24(17)14(10)18(28)29)22-15(26)12(23-30-2)11-9-32-19(20)21-11/h9,13,17H,3-8H2,1-2H3,(H3-,20,21,22,26,28,29)/b23-12-/t13-,17-/m1/s1 checkY
  • Key:HVFLCNVBZFFHBT-ZKDACBOMSA-N checkY
  (verify)

Cefepime is a fourth-generation cephalosporin antibiotic. Cefepime has an extended spectrum of activity against Gram-positive and Gram-negative bacteria, with greater activity against both types of organism than third-generation agents. A 2007 meta-analysis suggested when data of trials were combined, mortality was increased in people treated with cefepime compared with other β-lactam antibiotics.[1] In response, the U.S. Food and Drug Administration (FDA) performed their own meta-analysis which found no mortality difference.[2]

Cefepime was patented in 1982 by Bristol-Myers Squibb and approved for medical use in 1994.[3] It is available as a generic drug and sold under a variety of trade names worldwide.[citation needed][4]

It was removed from the World Health Organization's List of Essential Medicines in 2019.[5]

  1. ^ Yahav D, Paul M, Fraser A, Sarid N, Leibovici L (May 2007). "Efficacy and safety of cefepime: a systematic review and meta-analysis". The Lancet. Infectious Diseases. 7 (5): 338–348. doi:10.1016/S1473-3099(07)70109-3. PMID 17448937.
  2. ^ "FDA Alert: Cefepime (marketed as Maxipime)". Information for Healthcare Professionals. Food and Drug Administration. Archived from the original on 2 November 2017. Retrieved 2 August 2009.
  3. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 496. ISBN 9783527607495. Archived from the original on 19 June 2021. Retrieved 19 September 2020.
  4. ^ "Cefepime (maxipime), large spectrum 4th generation cephalosporin, resistant to beta-lactamases]".
  5. ^ World Health Organization (2019). Executive summary: the selection and use of essential medicines 2019: report of the 22nd WHO Expert Committee on the selection and use of essential medicines. Geneva: World Health Organization. hdl:10665/325773. WHO/MVP/EMP/IAU/2019.05. License: CC BY-NC-SA 3.0 IGO.