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 [1-2]. It was removed from the World Health Organization's List of Essential Medicines in 2019.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
SMILES / InChI / InChIKey
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1996), UK (2017))
IUPAC Name Click here for help
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
International Nonproprietary Names Click here for help
INN number INN
6092 cefepime
Synonyms Click here for help
BMY-28142 | BMY28142 | CFPM | Maxipime® | Renapime®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefepime/VNRX-5133 | Cefepime | Cefepime + enmetazobactam (Exblifep)
Other databases
BindingDB Ligand 50350470
CAS Registry No. 88040-23-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL186
DrugCentral Ligand 535
GtoPdb PubChem SID 405560213
PubChem CID 5479537
Search Google for chemical match using the InChIKey HVFLCNVBZFFHBT-ZKDACBOMSA-N
Search Google for chemicals with the same backbone HVFLCNVBZFFHBT
Search PubMed clinical trials cefepime
Search PubMed titles cefepime
Search PubMed titles/abstracts cefepime
UniChem Compound Search for chemical match using the InChIKey HVFLCNVBZFFHBT-ZKDACBOMSA-N
UniChem Connectivity Search for chemical match using the InChIKey HVFLCNVBZFFHBT-ZKDACBOMSA-N