AntibioticMech

linezolid

CHEBI:63607 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

An organofluorine compound that consists of 1,3-oxazolidin-2-one bearing an N-3-fluoro-4-(morpholin-4-yl)phenyl group as well as an acetamidomethyl group at position 5. A synthetic antibacterial agent that inhibits bacterial protein synthesis by binding to a site on 23S ribosomal RNA of the 50S subunit and prevents further formation of a functional 70S initiation complex. — 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

oxazolidinone antibioticARO:3000079

Strictly broader compounds or drug classes this molecule belongs to.

Chemical structure

Computed structure properties
Molecular formulaC16H20FN3O4
Charge0
Average mass337.351 Da
Monoisotopic mass337.14378 Da
SourceChEBI
InChIKeyTYZROVQLWOKYKF-ZDUSSCGKSA-N

SMILES

CC(=O)NC[C@H]1CN(c2ccc(N3CCOCC3)c(F)c2)C(=O)O1

InChI

InChI=1S/C16H20FN3O4/c1-11(21)18-9-13-10-20(16(22)24-13)12-2-3-15(14(17)8-12)19-4-6-23-7-5-19/h2-3,8,13H,4-7,9-10H2,1H3,(H,18,21)/t13-/m0/s1

Also called

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.

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
SourceNative IDLabelMinted CURIEVersion
ARO ARO:0000072 linezolid antibioticmech:aro-b680637e45 2026-08-30
CHEBI CHEBI:63607 linezolid antibioticmech:chebi-626e30d994 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.

50S ribosomal subunit P-site RIBOSOMAL_SUBUNIT DIRECT_BINDING_TARGET

ARO:3000757

CARD/ARO database assertion; target organism, strain, and assay are not specified. The 50S P-site is asserted as the target site. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

Mechanism summary

Mode of action
PROTEIN_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:48001 (protein synthesis inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.
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_TARGET_ALTERATION 7
ANTIBIOTIC_TARGET_ALTERATION
DeterminantARO IDOrganismGene familiesEvidence
23S rRNA with mutation conferring resistance to linezolid antibiotics ARO:3004057 not organism-specific —
  • ARO:3004057 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000072 (linezolid); database assertion, not a primary citation.)
Escherichia coli 23S rRNA with mutation conferring resistance to oxazolidinone antibiotics ARO:3004173 not organism-specific —
  • ARO:3004173 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000072 (linezolid); database assertion, not a primary citation.)
Mycobacterium tuberculosis 23S rRNA with mutation conferring resistance to linezolid ARO:3009345 not organism-specific —
  • ARO:3009345 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000072 (linezolid); database assertion, not a primary citation.)
Staphylococcus aureus 23S rRNA with mutation conferring resistance to linezolid ARO:3004058 not organism-specific —
  • ARO:3004058 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000072 (linezolid); database assertion, not a primary citation.)
cfr(B) ARO:3004649 not organism-specific —
  • ARO:3004649 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000072 (linezolid); database assertion, not a primary citation.)
cfr(D) ARO:3005021 not organism-specific —
  • ARO:3005021 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000072 (linezolid); database assertion, not a primary citation.)
clcD ARO:3004599 not organism-specific —
  • ARO:3004599 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000072 (linezolid); database assertion, not a primary citation.)
ANTIBIOTIC_TARGET_PROTECTION 2
ANTIBIOTIC_TARGET_PROTECTION
DeterminantARO IDOrganismGene familiesEvidence
optrA ARO:3003746 not organism-specific —
  • ARO:3003746 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000072 (linezolid); database assertion, not a primary citation.)
poxtA ARO:3004470 not organism-specific —
  • ARO:3004470 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000072 (linezolid); database assertion, not a primary citation.)
ANTIBIOTIC_EFFLUX 1
ANTIBIOTIC_EFFLUX
DeterminantARO IDOrganismGene familiesEvidence
Staphylococcus aureus LmrS ARO:3004572 not organism-specific —
  • ARO:3004572 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000072 (linezolid); database assertion, not a primary citation.)

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

Provenance

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