cefixime

CHEBI:472657 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A third-generation cephalosporin antibiotic bearing vinyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It is used in the treatment of gonorrhoea, tonsilitis, pharyngitis, bronchitis, and urinary tract infections. — 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
ARO:0000032 ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C16H15N5O7S2
Charge	0
Average mass	453.458 Da
Monoisotopic mass	453.04129 Da
Source	ChEBI
InChIKey	OKBVVJOGVLARMR-QSWIMTSFSA-N

SMILES

[H][C@]12SCC(C=C)=C(C(=O)O)N1C(=O)[C@H]2NC(=O)/C(=N\OCC(=O)O)c1csc(N)n1

InChI

InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1

Also called

cefixima (INN)— chebi
cefiximum (INN)— chebi
7β-{(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido}-3-ethenyl-3,4-didehydrocepham-4-carboxylic acid (EXACT_SYNONYM)— chebi
(6R,7R)-7-({(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetyl}amino)-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
(−)-cefixim (EXACT_SYNONYM)— chebi
CFM (EXACT_SYNONYM)— aro
necopen (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000646
beilstein:6025058
cas:79350-37-1
drugbank:DB00671
drugcentral:537
kegg.compound:C06881
kegg.drug:D00258
patent:EP30630
patent:US4409214
chembl:CHEMBL1541
pubchem.compound:5362065

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:3000646`	cefixime	`antibioticmech:aro-6fbe9bca14`	2026-08-30
CHEBI	`CHEBI:472657`	cefixime	`antibioticmech:chebi-1371a3fd71`	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:3000646 (cefixime); database assertion, not a primary citation.)

Resistance mechanisms

8 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 6

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
CMY-2	ARO:3002013	not organism-specific	—	ARO:3002013 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000646 (cefixime); database assertion, not a primary citation.)
CTX-M-27	ARO:3001889	not organism-specific	—	ARO:3001889 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000646 (cefixime); database assertion, not a primary citation.)
CTX-M-3	ARO:3001866	not organism-specific	—	ARO:3001866 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000646 (cefixime); database assertion, not a primary citation.)
PDC-3	ARO:3002500	not organism-specific	—	ARO:3002500 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000646 (cefixime); database assertion, not a primary citation.)
PDC-5	ARO:3002502	not organism-specific	—	ARO:3002502 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000646 (cefixime); database assertion, not a primary citation.)
blaS1	ARO:3005111	not organism-specific	—	ARO:3005111 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000646 (cefixime); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 2

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Neisseria gonorrhoeae PBP2 conferring resistance to beta-lactam antibiotics	ARO:3004832	not organism-specific	—	ARO:3004832 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000646 (cefixime); database assertion, not a primary citation.)
Neisseria meningititis PBP2 conferring resistance to beta-lactam	ARO:3003937	not organism-specific	—	ARO:3003937 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000646 (cefixime); 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.