linezolid

CHEBI:63607 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

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

Classification

oxazolidinone antibioticARO:3000079

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:22160
Label unavailable CHEBI:37143
Label unavailable CHEBI:38785
Label unavailable CHEBI:55374
oxazolidinone antibiotic ARO:3000079

Chemical structure

Computed structure properties
Molecular formula	C16H20FN3O4
Charge	0
Average mass	337.351 Da
Monoisotopic mass	337.14378 Da
Source	ChEBI
InChIKey	TYZROVQLWOKYKF-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

N-({(5S)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (EXACT_SYNONYM)— chebi
Linezolid (EXACT_SYNONYM)— chebi
N-(((S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide (EXACT_SYNONYM)— chebi
Zyvox (EXACT_SYNONYM)— aro
Zyvoxa (EXACT_SYNONYM)— aro
Zyvoxam (EXACT_SYNONYM)— aro
Zyvoxid (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.

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.

Patents and articles

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

Activity roles

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

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: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).

ARO:3000757 (CARD/ARO asserts targeted_by_antibiotic ARO:0000072 (linezolid); database assertion, not a primary citation.)

50S ribosomal peptidyl-transferase-center A-site pocket RIBOSOMAL_SUBUNIT DIRECT_BINDING_TARGET

A linezolid-bound D. radiodurans 50S crystal structure localized the drug in the PTC A-site pocket and showed nonproductive U2585 and tRNA-positioning effects. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2008-08 (retrieved 2026-09-02).

Deinococcus radiodurans NCBITaxon:1299

PMID:18757750 (Primary linezolid-bound 50S structural mechanism study (DOI:10.1073/pnas.0804276105).)

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION host shared target — CURATOR: PMID:18757750 resolved linezolid in the A-site pocket of the Deinococcus radiodurans 50S peptidyl-transferase center. It overlaps the aminoacyl group of A-site tRNA and stabilizes a nonproductive conformation of conserved 23S-rRNA nucleotide U2585, perturbing tRNA positioning.
Clinical status: APPROVED

Activity spectrum

Measured or curated activity against specific taxa. A number without a method is not an observation — every row here carries an assay.

273 observations · Browse all observations · Complete record (JSON.gz)

Observations 1–20 of 273

Activity observations
Organism	Activity	MIC	Disk diffusion	Assay	Strain	Sample/genome	Evidence
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960	—	79 source isolates 79 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; liquid media; MGIT; MGIT960	—	4536 source isolates 4536 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; not specified	—	5 source isolates 5 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2020; solid media	—	1 source isolates 1 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2020; solid media	—	97 source isolates 97 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	RESISTANT	—	—	CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960	—	24 source isolates 24 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2023; liquid media; MGIT; MGIT960	—	1065 source isolates 1065 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2023; not specified	—	1 source isolates 1 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	—	—	CRyPTIC DST; CLIRES2023; solid media	—	10 source isolates 10 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.06 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L	—	138 source isolates 138 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.06 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L	—	50 source isolates 50 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.06 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L	—	11 source isolates 11 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.12 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L	—	380 source isolates 380 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.12 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L	—	88 source isolates 88 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.12 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L	—	84 source isolates 84 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.25 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L	—	1138 source isolates 1138 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.25 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L	—	184 source isolates 184 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.25 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L	—	330 source isolates 330 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.5 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L	—	2644 source isolates 2644 measurements	Evidence Page data (JSON.gz)
Mycobacterium tuberculosis complex	SUSCEPTIBLE	0.5 mg/L	—	CRyPTIC DST; CRyPTIC; liquid media; microdilution plate; UKMYC5; critical concentration 1.0 mg/L	—	218 source isolates 218 measurements	Evidence Page data (JSON.gz)

Resistance mechanisms

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

ANTIBIOTIC_TARGET_ALTERATION 7

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
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
Determinant	ARO ID	Organism	Gene families	Evidence
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
Determinant	ARO ID	Organism	Gene families	Evidence
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.)

Record-level evidence

PMID:18757750 (Primary exact-linezolid ribosome-bound structural mechanism study.)

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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI/CARD identity, structure, roles, class, retained FDA status, and CARD target/resistance provenance; curator-confirmed protein synthesis inhibition and added the directly bound 50S A-site target.
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted
Added three DOI-backed linezolid-resistant Enterococcus faecium isolate MIC observations from Freitas et al. 2020.
CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted
Added five CDC/FDA AR Isolate Bank linezolid-resistant Staphylococcus activity observations for AR-0701, AR-0702, AR-0726, AR-0729, and AR-0730.
CURATED_RESISTANT_TAXA 2026-09-13 · codex · LLM-assisted
Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 linezolid-resistant Enterococcus faecalis activity observation for AR-0780.
STRUCTURED_ACTIVITY_BIOSAMPLE_ACCESSIONS 2026-09-26 · codex · LLM-assisted
Structured BioSample accessions on 5 activity_spectrum observation(s) where evidence notes already named exactly one accession.
RESEEDED_FROM_SOURCES 2026-09-26 · seed_from_sources
Re-seeded; changed: activity_spectrum (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.
RESEEDED_FROM_SOURCES 2026-10-05 · seed_from_sources
Re-seeded; changed: activity_membership_collections (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.

Provenance

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

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