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.

cephalosporin CHEBI:23066
cephalosporin 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

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

antimicrobial agent CHEBI:33281
antibacterial drug 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.)

Activity spectrum

Measured or curated activity against specific taxa. A number without a method is not an observation — every row here carries an assay.

2 observations · Browse all observations · Complete record (JSON.gz)

Activity observations
Organism	Activity	MIC	Disk diffusion	Assay	Strain	Sample/genome	Evidence
Neisseria gonorrhoeae NCBITaxon:485	—	1.0 mg/L	—	Broth microdilution cefixime MIC; modal MIC reported; interpreted using CLSI 2026 M100 Ed36.	1280	BioSample SAMN35332250	Evidence Page data (JSON.gz)
Neisseria gonorrhoeae NCBITaxon:485	—	>1.0 mg/L	—	Broth microdilution cefixime MIC; modal MIC reported; interpreted using CLSI 2026 M100 Ed36.	1281	BioSample SAMN35332251	Evidence Page data (JSON.gz)

Resistance mechanisms

8 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

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
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_RESISTANT_TAXA 2026-09-13 · codex · LLM-assisted
Added two stable-URL CDC/FDA AR Isolate Bank Panel 10 cefixime-resistant Neisseria gonorrhoeae MIC observations for AR-1280 and AR-1281.
STRUCTURED_ACTIVITY_BIOSAMPLE_ACCESSIONS 2026-09-26 · codex · LLM-assisted
Structured BioSample accessions on 2 activity_spectrum observation(s) where evidence notes already named exactly one accession.

Provenance

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

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