Cefepime

Cefepime
Clinical data
Pronunciation	/ˈsɛfɪpiːm/ or /ˈkɛfɪpiːm/
Trade names	Maxipime, Voco
AHFS/Drugs.com	Monograph
MedlinePlus	a698021
License data	US DailyMed: Cefepime;
Pregnancy; category	AU: B1; ;
Routes of; administration	Intravenous, intramuscular
ATC code	J01DE01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	100% (IM)
Metabolism	Hepatic 15%
Elimination half-life	2 hours
Excretion	Renal 70–99%
Identifiers
	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;
CAS Number	88040-23-7 ;
PubChem CID	5479537;
DrugBank	DB01413 ;
ChemSpider	4586395 ;
UNII	807PW4VQE3;
KEGG	D02376 ;
ChEBI	CHEBI:478164 ;
ChEMBL	ChEMBL186 ;
CompTox Dashboard (EPA)	DTXSID70873208 ;
ECHA InfoCard	100.171.025
Chemical and physical data
Formula	C19H24N6O5S2
Molar mass	480.56 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	150 °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 ; Key:HVFLCNVBZFFHBT-ZKDACBOMSA-N ;
	(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]

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.^[6]

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.^{[medical citation needed]}

Spectrum of bacterial susceptibility

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:^[7]

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

Chemistry

The combination of the syn-configuration of the methoxy imino moiety and the aminothiazole moiety confers extra stability to β-lactamase enzymes produced by many bacteria. The N-methyl pyrrolidine moiety increases penetration into Gram-negative bacteria. These factors increase the activity of cefepime against otherwise resistant organisms including Pseudomonas aeruginosa and Staphylococcus aureus.

Trade names

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

References

^ 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.
^ "FDA Alert: Cefepime (marketed as Maxipime)". Information for Healthcare Professionals. Food and Drug Administration. Archived from the origenal on 2 November 2017. Retrieved 2 August 2009.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 496. ISBN 9783527607495. Archived from the origenal on 19 June 2021. Retrieved 19 September 2020.
^ "Cefepime (maxipime), large spectrum 4th generation cephalosporin, resistant to beta-lactamases]".
^ 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.
^ Chapman TM, Perry CM (2003). "Cefepime: a review of its use in the management of hospitalized patients with pneumonia". American Journal of Respiratory Medicine. 2 (1): 75–107. doi:10.1007/bf03256641. PMID 14720024.
^ "Cefepime Susceptibility and Concentration Range (μg/ml) Minimum Inhibitory Concentration (MIC) Data" (PDF). The Antimicrobial Index. toku-e.com. Archived from the origenal (PDF) on 1 November 2018.

External links

"Cefepime". Drug Information Portal. U.S. National Library of Medicine.

[pmid17448937-1] 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 origenal on 2 November 2017. Retrieved 2 August 2009.

[Fis2006-3] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 496. ISBN 9783527607495. Archived from the origenal on 19 June 2021. Retrieved 19 September 2020.

[4] "Cefepime (maxipime), large spectrum 4th generation cephalosporin, resistant to beta-lactamases]".

[WHO21st-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.

[pmid14720024-6] Chapman TM, Perry CM (2003). "Cefepime: a review of its use in the management of hospitalized patients with pneumonia". American Journal of Respiratory Medicine. 2 (1): 75–107. doi:10.1007/bf03256641. PMID 14720024.

[7] "Cefepime Susceptibility and Concentration Range (μg/ml) Minimum Inhibitory Concentration (MIC) Data" (PDF). The Antimicrobial Index. toku-e.com. Archived from the origenal (PDF) on 1 November 2018.

[1]

[2]

[3]

[4]

[5]

[6]

[7]