cefepime

CHEBI:478164 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

cephalosporinARO:0000032

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:23066 CHEBI:23066
CHEBI:36816 CHEBI:36816
ARO:0000032 ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C19H24N6O5S2
Charge	0
Average mass	480.572 Da
Monoisotopic mass	480.12496 Da
Source	ChEBI
InChIKey	HVFLCNVBZFFHBT-ZKDACBOMSA-N

SMILES

[H][C@]12SCC(C[N+]3(C)CCCC3)=C(C(=O)[O-])N1C(=O)[C@H]2NC(=O)/C(=N\OC)c1csc(N)n1

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

Also called

cefepima (INN)— chebi
cefepimum (INN)— chebi
7β-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(1-methylpyrrolidinium-1-yl)methyl]-3,4-didehydrocepham-4-carboxylate (EXACT_SYNONYM)— chebi
(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 (EXACT_SYNONYM)— chebi
CFPM (EXACT_SYNONYM)— chebi
Cefepime (EXACT_SYNONYM)— chebi
Axepim (EXACT_SYNONYM)— aro
Cefepima (EXACT_SYNONYM)— aro
Cefepimum (EXACT_SYNONYM)— aro
FEP (EXACT_SYNONYM)— aro
Maxipime (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:0000059
cas:88040-23-7
drugbank:DB01413
drugcentral:535
kegg.compound:C08111
kegg.drug:D02376
patent:DE3307550
patent:US4406899
reaxys:7453587
wikipedia.en:Cefepime
chembl:CHEMBL186
pubchem.compound:5479537

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33281 CHEBI:33281
CHEBI:36047 CHEBI:36047

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:0000059`	cefepime	`antibioticmech:aro-3c50c3a1cf`	2026-08-30
CHEBI	`CHEBI:478164`	cefepime	`antibioticmech:chebi-7ff51e1b9f`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

beta-lactam sensitive penicillin-binding protein PROTEIN DIRECT_BINDING_TARGET

ARO:3000749

CARD/ARO database assertion; target organism, strain, and assay are not specified. Penicillin-binding proteins are asserted as inhibited transpeptidases. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000749 (CARD/ARO asserts targeted_by_antibiotic ARO:0000059 (cefepime); database assertion, not a primary citation.)

Resistance mechanisms

13 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_INACTIVATION 8

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
ACC-1	ARO:3001815	not organism-specific	—	ARO:3001815 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000059 (cefepime); database assertion, not a primary citation.)
Acinetobacter baumannii ampC beta-lactamase	ARO:3003796	not organism-specific	—	ARO:3003796 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000059 (cefepime); database assertion, not a primary citation.)
KPC-123	ARO:3007196	not organism-specific	—	ARO:3007196 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000059 (cefepime); database assertion, not a primary citation.)
LAP-1	ARO:3004825	not organism-specific	—	ARO:3004825 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000059 (cefepime); database assertion, not a primary citation.)
LAP-2	ARO:3004826	not organism-specific	—	ARO:3004826 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000059 (cefepime); database assertion, not a primary citation.)
LAQ-1	ARO:3007438	not organism-specific	—	ARO:3007438 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000059 (cefepime); database assertion, not a primary citation.)
SCO-1	ARO:3004856	not organism-specific	—	ARO:3004856 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000059 (cefepime); database assertion, not a primary citation.)
VIM-63	ARO:3005511	not organism-specific	—	ARO:3005511 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000059 (cefepime); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 3

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
Escherichia coli ompF with mutation conferring resistance to beta-lactam antibiotics	ARO:3003390	not organism-specific	—	ARO:3003390 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000059 (cefepime); database assertion, not a primary citation.)
Klebsiella aerogenes Omp36	ARO:3003385	not organism-specific	—	ARO:3003385 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000059 (cefepime); database assertion, not a primary citation.)
Klebsiella pneumoniae OmpK35	ARO:3003966	not organism-specific	—	ARO:3003966 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000059 (cefepime); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 2

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
AxyXY-OprZ	ARO:3004141	not organism-specific	—	ARO:3004141 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000059 (cefepime); database assertion, not a primary citation.)
Klebsiella pneumoniae KpnEF	ARO:3004585	not organism-specific	—	ARO:3004585 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000059 (cefepime); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.