ceftaroline

CHEBI:70729 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A cephalosporin that is the active metabolite of the prodrug ceftaroline fosamil. Used for the treatment of adults with acute bacterial skin and skin structure 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
Label unavailable CHEBI:35285
Label unavailable CHEBI:36816
Label unavailable CHEBI:38099
Label unavailable CHEBI:38418
cephalosporin ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C22H20N8O5S4
Charge	0
Average mass	604.721 Da
Monoisotopic mass	604.04395 Da
Source	ChEBI
InChIKey	RGFBRLNVZCCMSV-BIRGHMBHSA-N

SMILES

[H][C@]12SCC(Sc3nc(-c4cc[n+](C)cc4)cs3)=C(C(=O)[O-])N1C(=O)[C@H]2NC(=O)/C(=N\OCC)c1nsc(N)n1

InChI

InChI=1S/C22H20N8O5S4/c1-3-35-27-13(16-26-21(23)39-28-16)17(31)25-14-18(32)30-15(20(33)34)12(9-36-19(14)30)38-22-24-11(8-37-22)10-4-6-29(2)7-5-10/h4-8,14,19H,3,9H2,1-2H3,(H3-,23,25,26,28,31,33,34)/b27-13-/t14-,19-/m1/s1

Also called

(6R,7R)-7-{[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetyl]amino}-3-{[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (EXACT_SYNONYM)— chebi
PPI 0903M (EXACT_SYNONYM)— chebi
T 91825 (EXACT_SYNONYM)— chebi
T-91825 (EXACT_SYNONYM)— chebi
CPT (EXACT_SYNONYM)— aro
T91825 (EXACT_SYNONYM)— aro
ceftaroline fosamil (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.

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:3000651`	ceftaroline	`antibioticmech:aro-c685757b90`	2026-08-30
CHEBI	`CHEBI:70729`	ceftaroline	`antibioticmech:chebi-2e0316ebf1`	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:3000651 (ceftaroline); database assertion, not a primary citation.)

Resistance mechanisms

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

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Escherichia coli PBP3 mutants conferring resistance to beta-lactam antibiotics	ARO:3007423	not organism-specific	—	ARO:3007423 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000651 (ceftaroline); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_REPLACEMENT 1

ANTIBIOTIC_TARGET_REPLACEMENT
Determinant	ARO ID	Organism	Gene families	Evidence
mecA	ARO:3000617	not organism-specific	—	ARO:3000617 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000651 (ceftaroline); 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 (YAML).

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