Cefepime

{{Short description|Fourth-generation Cephalosporin Antibiotic}}

{{Use dmy dates|date=September 2019}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| verifiedrevid = 458746257

| drug_name =

| 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

| image = Cefepime2DCSD.svg

| width = 300px

| image2 = Cefepime ball-and-stick model from xtal 2018.png

| width2 = 300px

| pronounce = {{IPAc-en|ˈ|s|ɛ|f|ᵻ|p|iː|m}} or {{IPAc-en|ˈ|k|ɛ|f|ᵻ|p|iː|m}}

| tradename = Maxipime, Voco

| Drugs.com = {{drugs.com|monograph|cefepime-hydrochloride}}

| MedlinePlus = a698021

| pregnancy_AU = B1

| pregnancy_US = B

| pregnancy_category=

| DailyMedID = Cefepime

| legal_AU = S4

| legal_CA = Rx-only

| legal_UK = POM

| legal_US = Rx-only

| routes_of_administration = Intravenous, intramuscular

| bioavailability = 100% (IM)

| metabolism = Hepatic 15%

| elimination_half-life = 2 hours

| excretion = Renal 70–99%

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 88040-23-7

| ATC_prefix = J01

| ATC_suffix = DE01

| PubChem = 5479537

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01413

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4586395

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 807PW4VQE3

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D02376

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 478164

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 186

| C=19 | H=24 | N=6 | O=5 | S=2

| 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HVFLCNVBZFFHBT-ZKDACBOMSA-N

| melting_point = 150

| melting_notes = (dec.)

}}

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.{{cite journal | vauthors = Yahav D, Paul M, Fraser A, Sarid N, Leibovici L | title = Efficacy and safety of cefepime: a systematic review and meta-analysis | journal = The Lancet. Infectious Diseases | volume = 7 | issue = 5 | pages = 338–348 | date = May 2007 | pmid = 17448937 | doi = 10.1016/S1473-3099(07)70109-3 }} In response, the U.S. Food and Drug Administration (FDA) performed their own meta-analysis which found no mortality difference.{{cite web |url=https://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/DrugSafetyInformationforHeathcareProfessionals/ucm167254.htm |work = Information for Healthcare Professionals | title = FDA Alert: Cefepime (marketed as Maxipime) | publisher = Food and Drug Administration |access-date=2009-08-02 |archive-date=2 November 2017 |archive-url=https://web.archive.org/web/20171102213540/https://www.fda.gov/Drugs/DrugSafety/PostmarketDrugSafetyInformationforPatientsandProviders/DrugSafetyInformationforHeathcareProfessionals/ucm167254.htm |url-status=dead }}

Cefepime was patented in 1982 by Bristol-Myers Squibb and approved for medical use in 1994.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=496 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA496 |access-date=19 September 2020 |archive-date=19 June 2021 |archive-url=https://web.archive.org/web/20210619051212/https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA496 |url-status=live }} It is available as a generic drug and sold under a variety of trade names worldwide.{{citation needed|date=September 2019}}{{Cite news |title=Cefepime (maxipime), large spectrum 4th generation cephalosporin, resistant to beta-lactamases].}}

It was removed from the World Health Organization's List of Essential Medicines in 2019.{{cite book | vauthors = ((World Health Organization)) | year = 2019 | title = 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 | publisher = World Health Organization | location = Geneva | author-link = World Health Organization | hdl = 10665/325773 | id = WHO/MVP/EMP/IAU/2019.05. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}