CHEBI:478164 - cefepime

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ChEBI Name cefepime
ChEBI ID CHEBI:478164
Definition A cephalosporin bearing (1-methylpyrrolidinium-1-yl)methyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3486, CHEBI:473919
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Formula C19H24N6O5S2
Net Charge 0
Average Mass 480.56100
Monoisotopic Mass 480.125
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
InChIKey HVFLCNVBZFFHBT-ZKDACBOMSA-N
SMILES [H][C@]12SCC(C[N+]3(C)CCCC3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\c1csc(N)n1)C([O-])=O
Roles Classification
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
drug allergen
Any drug which causes the onset of an allergic reaction.
(via cephalosporin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cefepime (CHEBI:478164) has role antibacterial drug (CHEBI:36047)
cefepime (CHEBI:478164) is a cephalosporin (CHEBI:23066)
cefepime (CHEBI:478164) is a oxime O-ether (CHEBI:36816)
cefepime (CHEBI:478164) is conjugate base of cefepime(1+) (CHEBI:59349)
Incoming cefepime(1+) (CHEBI:59349) is conjugate acid of cefepime (CHEBI:478164)
IUPAC Name
7β-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(1-methylpyrrolidinium-1-yl)methyl]-3,4-didehydrocepham-4-carboxylate
INNs Sources
cefepima ChemIDplus
cefepime ChemIDplus
cefepimum ChemIDplus
Synonyms Sources
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(1-methylpyrrolidinium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate IUPAC
Cefepime KEGG COMPOUND
cefepime ChEMBL
CFPM ChEBI
Manual Xrefs Databases
535 DrugCentral
C08111 KEGG COMPOUND
Cefepime Wikipedia
D02376 KEGG DRUG
DB01413 DrugBank
DE3307550 Patent
US4406899 Patent
View more database links
Registry Numbers Types Sources
7453587 Beilstein Registry Number Beilstein
7453587 Reaxys Registry Number Reaxys
88040-23-7 CAS Registry Number KEGG COMPOUND
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Last Modified
13 February 2018
General Comment
2011-03-18 A semi-synthetic fourth-generation cephalosporin antibiotic, cefepime shows greater activity than third-generation agents against both Gram-positive and Gram-negative organisms, and is used as its hydrochloride salt for treatment of severe nosocomial pneumonia, infections caused by multi-resistant microorganisms (e.g. Pseudomonas aeruginosa) and empirical treatment of febrile neutropenia.