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.

CHEBI:23066 CHEBI:23066
CHEBI:36816 CHEBI:36816
CHEBI:38418 CHEBI:38418
ARO:0000032 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

Equivalent identifiers for this same structure in other resources.

ARO:3000645
beilstein:1096643
cas:63527-52-6
drugbank:DB00493
drugcentral:546
kegg.compound:C06885
kegg.drug:D07647
patent:DE2556736
patent:DE2702501
patent:US4098888
patent:US4152432
pdb-ccd:CE3
reaxys:1096643
wikipedia.en:Cefotaxime
chembl:CHEMBL1730
pubchem.compound:5742673

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: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.)

Resistance mechanisms

20 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 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

Provenance

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