cefepime   Click here for help

GtoPdb Ligand ID: 10772

Synonyms: BMY-28142 | BMY28142 | CFPM | Maxipime® | Renapime®
Approved drug
cefepime is an approved drug (FDA (1996), UK (2017))
Compound class: Synthetic organic
Comment: Cefepime is a semisynthetic, broad-spectrum, fourth-generation cephalosporin antibacterial [1,4]. It was removed from the World Health Organization's List of Essential Medicines in 2019.

cefepime is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 203.58
Molecular weight 480.12
XLogP -3.06
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[N+]1(C)CCCC1
Isomeric SMILES CO/N=C(/c1csc(n1)N)\C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])C[N+]1(C)CCCC1
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
InChI Key HVFLCNVBZFFHBT-ZKDACBOMSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Cefepime is reserved for the treatment of severe nosocomial pneumonia, particularly infections caused by multi-resistant microorganisms such as Pseudomonas aeruginosa. It does not have a Europe-wide EMA authorisation but is approved by most of the individual nations.
Cefepime + taniborbactam (formerly VNRX-5133, an injectable beta-lactamase inhibitor with in vitro activity against both serine- and metallo-beta-lactamases) is proposed as an option for infections due to carbapenem-resistant Enterobacteriaceae and Pseudomonas aeruginosa, and to combat engineerable bioterror pathogens such as Burkholderia species. This combination has completed Phase 3 evaluation for efficacy in the treatment of complicated urinary tract infections (cUTIs; NCT03840148) [3,5]. Cefepime + enmetazobactam has also been evaluated for the treatment of cUTIs [2]. The combination (Exblifep®) was FDA approved for this indication in February 2024 and by the EMA the following month.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03840148 Safety and Efficacy Study of Cefepime/VNRX-5133 in Patients With Complicated Urinary Tract Infections (CERTAIN-1) Phase 3 Interventional VenatoRx Pharmaceuticals, Inc. A study examining the combination of the 4th gen cephalosporin cefepime and the broad-spectrum β-lactamse inhibitor taniborbactam. 3,5
NCT03687255 Safety and Efficacy Study of Cefepime-AAI101 in the Treatment of Complicated Urinary Tract Infections Phase 3 Interventional Allecra 2
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com