Cefepime

Cefepime
Names
Pronunciation/ˈsɛfɪpiːm/ or /ˈkɛfɪpiːm/
Trade namesMaxipime, Voco, Renapime, others
Other namesCephepime
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
Drug classAntibiotic (4th generation cephalosporin)[1]
Main usesBacterial infections[2]
Side effectsDiarrhea, nausea, rash, pain at the site of injection[2]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • AU: B1
  • US: B (No risk in non-human studies)
    Routes of
    use    		Intravenous, intramuscular
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa698021
    Legal
    Legal status
    Pharmacokinetics
    Bioavailability100% (IM)
    MetabolismLiver 15%
    Elimination half-life2 hours
    ExcretionKidney 70–99%
    Chemical and physical data
    FormulaC19H24N6O5S2
    Molar mass480.56 g·mol−1
    3D model (JSmol)
    Melting point150 °C (302 °F) (dec.)
    SMILES
    • 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
    • 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

    Cefepime, sold under the brand name Renapime among others, is an antibiotic used to treat intra abdominal infections, respiratory tract infections, skin and skin structure infections, urinary tract infections, meningitis, endocarditis, and sepsis.[2][3] It works against both gram positive and gram negative bacteria.[4] It is given by injection into a vein or muscle.[3]

    Common side effects include diarrhea, nausea, rash, and pain at the site of injection.[2] Other side effects may include allergic reactions, Clostridioides difficile infection, and encephalopathy.[2] There is no evidence of harm in pregnancy but such use has not been well studied.[5] It is a fourth-generation cephalosporin.[1]

    Cefepime was patented in 1982 and approved for medical use in 1994.[6] It is available as a generic medication.[7] In the United Kingdom 10 doses of 2 grams costs the NHS about £110 as of 2021.[3] This amount in the United States is about 70 USD.[8] It was removed from the World Health Organization's List of Essential Medicines in 2019.[9]

    Medical use

    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.[10]

    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.

    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.

    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.[11] In response, the U.S. Food and Drug Administration (FDA) performed their own meta-analysis which found no mortality difference.[12]

    Spectrum of activity

    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 Streptococcus species. The following represents MIC susceptibility data for a few medically significant microorganisms:[13]

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

    Dosage

    It is given at a dose of 500 to 2,000 mg twice per day and occasionally three times per day.[3]

    Chemistry

    The combination of the syn-configuration of the methoxyimino moiety and the aminothiazole 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.

    History

    Cefepime was patented in 1982 by Bristol-Myers Squibb and approved for medical use in 1994.[6]

    Society and culture

    Brand names

    Following expiration of the Bristol-Myers Squibb patent, cefepime became available as a generic and is now marketed by numerous companies worldwide under tradenames including Neopime (Neomed), Maxipime, Cepimax, Cepimex, and Axepim.

    References

    1. 1 2 Beauduy, Camille E.; Winston, Lisa G. (2020). "43. Beta-lactam and other cell wall - & membrane - active antibiotics". In Katzung, Bertram G.; Trevor, Anthony J. (eds.). Basic and Clinical Pharmacology (15th ed.). New York: McGraw-Hill. p. 833. ISBN 978-1-260-45231-0. Archived from the original on 10 October 2021. Retrieved 30 November 2021.
    2. 1 2 3 4 5 "Cefepime Monograph for Professionals". Drugs.com. Archived from the original on 19 January 2021. Retrieved 30 December 2021.
    3. 1 2 3 4 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 561. ISBN 978-0857114105.
    4. ↑ "Cephalosporins". LiverTox: Clinical and Research Information on Drug-Induced Liver Injury. National Institute of Diabetes and Digestive and Kidney Diseases. 2012. Archived from the original on 1 November 2021. Retrieved 30 December 2021.
    5. ↑ "Cefepime (Maxipime) Use During Pregnancy". Drugs.com. Archived from the original on 29 November 2020. Retrieved 30 December 2021.
    6. 1 2 Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 496. ISBN 9783527607495. Archived from the original on 19 June 2021. Retrieved 26 July 2021.
    7. ↑ "Cefepime Prices, Coupons & Savings Tips - GoodRx". GoodRx. Retrieved 30 December 2021.
    8. ↑ "Cefepime Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 12 August 2020. Retrieved 30 December 2021.
    9. ↑ 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.
    10. ↑ 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.
    11. ↑ 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.
    12. ↑ "Information for Healthcare Professionals: Cefepime (marketed as Maxipime)". Archived from the original on 2 November 2017. Retrieved 2 August 2009.
    13. ↑ "Archive copy" (PDF). Archived (PDF) from the original on 1 November 2018. Retrieved 26 July 2021.{{cite web}}: CS1 maint: archived copy as title (link)
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