cefotaxime

CHEBI:204928 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A cephalosporin compound having acetoxymethyl and [2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups. — 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
Label unavailable CHEBI:36816
Label unavailable CHEBI:38418
cephalosporin ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C16H17N5O7S2
Charge	0
Average mass	455.474 Da
Monoisotopic mass	455.05694 Da
Source	ChEBI
InChIKey	GPRBEKHLDVQUJE-QSWIMTSFSA-N

SMILES

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

InChI

InChI=1S/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9-/t10-,14-/m1/s1

Also called

cefotaxima (INN)— chebi
cefotaximum (INN)— chebi
3-(acetoxymethyl)-7β-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3,4-didehydrocepham-4-carboxylic acid (EXACT_SYNONYM)— chebi
(6R,7R)-3-(acetoxymethyl)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
(6R,7R)-3-Acetoxymethyl-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
(6R,7R,Z)-3-(acetoxymethyl)-7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
Cephotaxime (EXACT_SYNONYM)— chebi
CTX (EXACT_SYNONYM)— aro
cefotaxime acid (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:3000645`	cefotaxime	`antibioticmech:aro-dc40265400`	2026-08-30
CHEBI	`CHEBI:204928`	cefotaxime	`antibioticmech:chebi-4a4bc5cba7`	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:3000645 (cefotaxime); 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.

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

Activity observations
Organism	Activity	MIC	Disk diffusion	Assay	Strain	Sample/genome	Evidence
Escherichia coli NCBITaxon:562	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	0349	BioSample SAMN11953777	Evidence Page data (JSON.gz)
Klebsiella pneumoniae NCBITaxon:573	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	0497	BioSample SAMN11953783	Evidence Page data (JSON.gz)
Acinetobacter baumannii NCBITaxon:470	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2024 M100 S34.	0297	BioSample SAMN04901687	Evidence Page data (JSON.gz)
Escherichia coli NCBITaxon:562	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	0346	BioSample SAMN11953774	Evidence Page data (JSON.gz)
Escherichia coli NCBITaxon:562	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1305	BioSample SAMN46941623	Evidence Page data (JSON.gz)
Klebsiella pneumoniae NCBITaxon:573	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1149	BioSample SAMN34111336	Evidence Page data (JSON.gz)
Enterobacter cloacae complex NCBITaxon:354276	—	32.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1150	BioSample SAMN34111337	Evidence Page data (JSON.gz)
Enterobacter cloacae complex NCBITaxon:354276	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1151	BioSample SAMN34111338	Evidence Page data (JSON.gz)
Enterobacter cloacae complex NCBITaxon:354276	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1152	BioSample SAMN34111339	Evidence Page data (JSON.gz)
Klebsiella pneumoniae NCBITaxon:573	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1153	BioSample SAMN34111340	Evidence Page data (JSON.gz)
Klebsiella pneumoniae NCBITaxon:573	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1158	BioSample SAMN34111344	Evidence Page data (JSON.gz)
Enterobacter cloacae complex NCBITaxon:354276	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1160	BioSample SAMN34111346	Evidence Page data (JSON.gz)
Escherichia coli NCBITaxon:562	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1162	BioSample SAMN34111348	Evidence Page data (JSON.gz)
Klebsiella pneumoniae NCBITaxon:573	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	1163	BioSample SAMN34111349	Evidence Page data (JSON.gz)
Escherichia coli NCBITaxon:562	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35.	0495	BioSample SAMN11953781	Evidence Page data (JSON.gz)
Acinetobacter baumannii NCBITaxon:470	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; CDC/FDA AR Isolate Bank reports an R interpretation without a versioned breakpoint footnote on this isolate page.	0033	BioSample SAMN04014874	Evidence Page data (JSON.gz)
Acinetobacter baumannii NCBITaxon:470	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2024 M100 S34 per the CDC/FDA AR Isolate Bank Panel 1227 footnote.	0078	BioSample SAMN04014919	Evidence Page data (JSON.gz)
Acinetobacter baumannii NCBITaxon:470	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2020 M100 S30 per the CDC/FDA AR Isolate Bank Panel 1227 footnote.	0083	BioSample SAMN04014924	Evidence Page data (JSON.gz)
Salmonella enterica subsp. enterica serovar Typhimurium NCBITaxon:90371	—	>64.0 mg/L	—	Broth microdilution cefotaxime MIC; modal MIC reported; interpreted using CLSI 2025 M100 S35 per the CDC/FDA AR Isolate Bank Panel 10 footnote.	0539	BioSample SAMN07688908	Evidence Page data (JSON.gz)

Resistance mechanisms

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

ANTIBIOTIC_INACTIVATION 14

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:3000645 (cefotaxime); database assertion, not a primary citation.)
ACC-2	ARO:3001816	not organism-specific	—	ARO:3001816 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
ACC-4	ARO:3001818	not organism-specific	—	ARO:3001818 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
ACI-1	ARO:3004359	not organism-specific	—	ARO:3004359 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
CAM-1	ARO:3004559	not organism-specific	—	ARO:3004559 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
CMY-136	ARO:3004854	not organism-specific	—	ARO:3004854 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
KPC-123	ARO:3007196	not organism-specific	—	ARO:3007196 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
PJM-1	ARO:3007374	not organism-specific	—	ARO:3007374 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
PRC-1	ARO:3007085	not organism-specific	—	ARO:3007085 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
SCO-1	ARO:3004856	not organism-specific	—	ARO:3004856 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
TEM-61	ARO:3000930	not organism-specific	—	ARO:3000930 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
VAM-1	ARO:3007062	not organism-specific	—	ARO:3007062 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
VIM-63	ARO:3005511	not organism-specific	—	ARO:3005511 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
VMB-1	ARO:3005015	not organism-specific	—	ARO:3005015 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 2

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
CmeABC	ARO:3000773	not organism-specific	—	ARO:3000773 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
abcA	ARO:3003942	not organism-specific	—	ARO:3003942 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 2

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Haemophilus influenzae PBP3 conferring resistance to beta-lactam antibiotics	ARO:3004446	not organism-specific	—	ARO:3004446 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
Streptococcus pyogenes PBP2x conferring resistance to beta-lactam antibiotics	ARO:3007531	not organism-specific	—	ARO:3007531 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 2

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
Klebsiella pneumoniae OmpK37	ARO:3004122	not organism-specific	—	ARO:3004122 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); database assertion, not a primary citation.)
Serratia marcescens Omp1	ARO:3004128	not organism-specific	—	ARO:3004128 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000645 (cefotaxime); 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 2026-09-12 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank cefotaxime-resistant Escherichia coli isolate MIC observation.
CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank cefotaxime-resistant Klebsiella pneumoniae isolate MIC observation.
CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank cefotaxime-resistant Acinetobacter baumannii isolate MIC observation.
CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted
Corrected the CDC/FDA AR Isolate Bank 0349 breakpoint context from CLSI 2024 M100 S34 to CLSI 2025 M100 S35.
CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank cefotaxime-resistant Escherichia coli MIC observation from isolate 0346.
CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank cefotaxime-resistant Escherichia coli isolate MIC observation for AR-1305.
CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted
Added 9 stable-URL CDC/FDA AR Isolate Bank cefotaxime-resistant Multi-Mechanism panel MIC observations for AR-1149, AR-1150, AR-1151, AR-1152, AR-1153, AR-1158, AR-1160, AR-1162, and AR-1163.
CURATED_RESISTANT_TAXA 2026-09-17 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 cefotaxime-resistant Escherichia coli MIC observation for AR-0495.
CURATED_RESISTANT_TAXA 2026-09-18 · codex · LLM-assisted
Added CDC/FDA AR Isolate Bank Panel 1227 isolate 0033 Acinetobacter baumannii cefotaxime MIC >64 mg/L with interpretation R; preserved BioSample SAMN04014874 and Study ID CarbaNP-02 in evidence notes.
CURATED_RESISTANT_TAXA 2026-09-18 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1227 cefotaxime-resistant Acinetobacter baumannii MIC observation for AR-0078; preserved source Pus, BioSample SAMN04014919, Study ID CarbaNP-47, and MLST ST229(Pasteur)/ST203(Oxford) in evidence notes.
CURATED_RESISTANT_TAXA 2026-09-19 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank Panel 1227 cefotaxime-resistant Acinetobacter baumannii MIC observation for AR-0083; preserved source Unknown, BioSample SAMN04014924, Study ID CarbaNP-52, and MLST ST1(Pasteur)/ST231/1604(Oxford) in evidence notes.
CURATED_RESISTANT_TAXA 2026-09-20 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 cefotaxime-resistant Salmonella Typhimurium MIC observation for AR-0539; preserved source Stool, BioSample SAMN07688908, and Study ID NEW-23 in evidence notes.
STRUCTURED_ACTIVITY_BIOSAMPLE_ACCESSIONS 2026-09-26 · codex · LLM-assisted
Structured BioSample accessions on 19 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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