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.

CHEBI:23066 CHEBI:23066
CHEBI:35285 CHEBI:35285
CHEBI:36816 CHEBI:36816
CHEBI:38099 CHEBI:38099
CHEBI:38418 CHEBI:38418
ARO:0000032 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

Equivalent identifiers for this same structure in other resources.

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: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 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_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.