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
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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.

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Click here for structure editor
Physico-chemical Properties
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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.

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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
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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/)

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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/)
References
1. Fuchs PC, Jones RN, Barry AL, Thornsberry C. (1985)
Evaluation of the in vitro activity of BMY-28142, a new broad-spectrum cephalosporin.
Antimicrob Agents Chemother, 27 (5): 679-82. [PMID:3893316]
2. Kaye KS, Belley A, Barth P, Lahlou O, Knechtle P, Motta P, Velicitat P. (2022)
Effect of Cefepime/Enmetazobactam vs Piperacillin/Tazobactam on Clinical Cure and Microbiological Eradication in Patients With Complicated Urinary Tract Infection or Acute Pyelonephritis: A Randomized Clinical Trial.
JAMA, 328 (13): 1304-1314. [PMID:36194218]
3. Moeck G, Gasink LB, Mendes RE, Woosley LN, Dorr M, Chen H, Wagenlehner FM, Henkel T, McGovern PC. (2024)
Patient outcomes by baseline pathogen resistance phenotype and genotype in CERTAIN-1, a Phase 3 study of cefepime-taniborbactam versus meropenem in adults with complicated urinary tract infection.
Antimicrob Agents Chemother, 68 (7): e0023624. [PMID:38780262]
4. Tomatsu K, Ando S, Masuyoshi S, Hirano M, Miyaki T, Kawaguchi H. (1986)
Antibacterial activity of BMY-28142, a novel broad-spectrum cephalosporin.
J Antibiot, 39 (11): 1584-91. [PMID:3539901]
5. Wagenlehner FM, Gasink LB, McGovern PC, Moeck G, McLeroth P, Dorr M, Dane A, Henkel T, CERTAIN-1 Study Team. (2024)
Cefepime-Taniborbactam in Complicated Urinary Tract Infection.
N Engl J Med, 390 (7): 611-622. [PMID:38354140]