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]

^ 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 original 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 original 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.

[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 original 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 original 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.

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