cefuroxime

CHEBI:3515 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A 3-(carbamoyloxymethyl)cephalosporin compound having a 7-(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido side chain. — 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:24129 CHEBI:24129
CHEBI:28084 CHEBI:28084
CHEBI:36816 CHEBI:36816
ARO:0000032 ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C16H16N4O8S
Charge	0
Average mass	424.391 Da
Monoisotopic mass	424.06888 Da
Source	ChEBI
InChIKey	JFPVXVDWJQMJEE-IZRZKJBUSA-N

SMILES

[H][C@]12SCC(COC(N)=O)=C(C(=O)O)N1C(=O)[C@H]2NC(=O)/C(=N\OC)c1ccco1

InChI

InChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1

Also called

Sharox (BRAND_NAME)— chebi
Zinacef Danmark (BRAND_NAME)— chebi
cefuroximo (INN)— chebi
cefuroximum (INN)— chebi
3-[(carbamoyloxy)methyl]-7β-[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-3,4-didehydrocepham-4-carboxylic acid (EXACT_SYNONYM)— chebi
(6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-furan-2-yl-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
Cefuroxim (EXACT_SYNONYM)— chebi
Cefuroxime (EXACT_SYNONYM)— chebi
Cephuroxime (EXACT_SYNONYM)— chebi
Biofuroksym (EXACT_SYNONYM)— aro
CXM (EXACT_SYNONYM)— aro
Cefuril (EXACT_SYNONYM)— aro
Cefuroximo (EXACT_SYNONYM)— aro
Cefuroximum (EXACT_SYNONYM)— aro
Zinacef (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:0000063
cas:55268-75-2
drugbank:DB01112
drugcentral:565
kegg.compound:C06894
kegg.drug:D00262
metacyc.compound:CPD0-2069
patent:DE2439880
patent:DE2706413
patent:US3974153
patent:US4267320
reaxys:5783190
wikipedia.en:Cefuroxime
chembl:CHEMBL1436
pubchem.compound:5479529

Activity roles

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

CHEBI:33281 CHEBI:33281

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:0000063`	cefuroxime	`antibioticmech:aro-5a4b3112fe`	2026-08-30
CHEBI	`CHEBI:3515`	cefuroxime	`antibioticmech:chebi-6baa755c24`	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:0000063 (cefuroxime); database assertion, not a primary citation.)

Mechanism summary

Clinical status: APPROVED

Resistance mechanisms

10 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 10

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
ACC-4	ARO:3001818	not organism-specific	—	ARO:3001818 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000063 (cefuroxime); database assertion, not a primary citation.)
CAE-1	ARO:3007635	not organism-specific	—	ARO:3007635 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000063 (cefuroxime); database assertion, not a primary citation.)
CMY-136	ARO:3004854	not organism-specific	—	ARO:3004854 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000063 (cefuroxime); database assertion, not a primary citation.)
EBR-5	ARO:3007437	not organism-specific	—	ARO:3007437 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000063 (cefuroxime); database assertion, not a primary citation.)
LAP-1	ARO:3004825	not organism-specific	—	ARO:3004825 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000063 (cefuroxime); database assertion, not a primary citation.)
LAP-2	ARO:3004826	not organism-specific	—	ARO:3004826 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000063 (cefuroxime); database assertion, not a primary citation.)
MAB	ARO:3007180	not organism-specific	—	ARO:3007180 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000063 (cefuroxime); database assertion, not a primary citation.)
SCO-1	ARO:3004856	not organism-specific	—	ARO:3004856 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000063 (cefuroxime); database assertion, not a primary citation.)
SED-1	ARO:3003561	not organism-specific	—	ARO:3003561 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000063 (cefuroxime); database assertion, not a primary citation.)
YRC-1	ARO:3005035	not organism-specific	—	ARO:3005035 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000063 (cefuroxime); 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 2026-08-31 · 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.