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

Classification

cephalosporinARO:0000032

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:24129
• 3-(carbamoyloxymethyl)cephalosporin CHEBI:28084
• Label unavailable CHEBI:36816
• cephalosporin ARO:0000032

Chemical structure

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

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.

• cefuroximeARO:0000063
• cas:55268-75-2
• kegg.compound:C06894
• metacyc.compound:CPD0-2069
• reaxys:5783190
• chembl:CHEMBL1436
• pubchem.compound:5479529

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.

• drugbank:DB01112
• drugcentral:565
• kegg.drug:D00262

Patents and articles

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

• patent:DE2439880
• patent:DE2706413
• patent:US3974153
• patent:US4267320
• wikipedia.en:Cefuroxime

Activity roles

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

• antimicrobial agent 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.

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

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

6. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

7. RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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