Linezolid

Summary

Linezolid (CHEMBL126) is an approved small-molecule antibacterial drug (ATC J01XX08) targeting MAOA and MAOB; indicated across 23 conditions including pneumonia and bacterial infectious disease with sepsis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J01XX08
• Targets: 2 (MAOA, MAOB)
• Indications: 23 conditions
• Clinical trials: 132
• Chemistry: 337.35 Da · C16H20FN3O4

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL126
Name	Linezolid
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	441401
ChEBI	CHEBI:63607
ATC	J01XX08
Molecular formula	C16H20FN3O4
Molecular weight	337.35
InChIKey	TYZROVQLWOKYKF-ZDUSSCGKSA-N

SMILES: CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCOCC3)F

IUPAC name: N-[[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide

ChEBI definition: 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.

Pharmacological roles (ChEBI): antibacterial drug, protein synthesis inhibitor.

Also known as: Linezolid, Linezolide, Pnu-100766, U-100,766, U-100766, Zyvox, linezolid, Linezoid, SID26719842, SID49681612, LINEZOLID, Linelozide

Patent coverage: 7,703 distinct patent families (27,339 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 27,071 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
MAOA	Monoamine oxidase A	Inhibition	4.34	0.2%	P21397
MAOB	Monoamine oxidase B	Inhibition	5.68	0%	P27338

Broader ChEMBL bioactivity targets: 8 (assay-derived). Sample: Streptokinase A, Prelamin-A/C, Amine oxidase [flavin-containing] A, Amine oxidase [flavin-containing] B, Prostaglandin G/H synthase 1, Amine oxidase [flavin-containing] B, Calmodulin-like protein 3, Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial.

Bioactivity

ChEMBL activities: 14 potent at pChembl ≥ 5 of 22 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
P10520	6.8	EC50	158	nM	CHEMBL_ACT_4925497
MAOB	6.21	IC50	619	nM	CHEMBL_ACT_25731055
MAOB	6.21	IC50	619	nM	CHEMBL_ACT_25950035
MAOB	6.21	IC50	620	nM	CHEMBL_ACT_29220958
MAOB	5.68	IC50	2100	nM	CHEMBL_ACT_16402688
MAOB	5.36	IC50	4336	nM	CHEMBL_ACT_25996610
P10520	5.22	EC50	5998	nM	CHEMBL_ACT_4990564
MAOA	5.19	IC50	6520	nM	CHEMBL_ACT_25731052
MAOA	5.19	IC50	6520	nM	CHEMBL_ACT_25950026
MAOA	5.19	IC50	6520	nM	CHEMBL_ACT_29220945
MAOA	5.1	Ki	7900	nM	CHEMBL_ACT_13338208
PTGS1	5.09	IC50	8190	nM	CHEMBL_ACT_19036384
SDHA	5.09	IC50	8190	nM	CHEMBL_ACT_19036387
CALML3	5.03	IC50	9300	nM	CHEMBL_ACT_24700259

Target pathways

Aggregated over 2 target gene(s): MAOA, MAOB.

Top Reactome pathways

23 total, by targets touching each:

Pathway	Targets	Genes
Amine Oxidase reactions	2	MAOA, MAOB
Biogenic amines are oxidatively deaminated to aldehydes by MAOA and MAOB	2	MAOA, MAOB
Metabolism	2	MAOA, MAOB
Biological oxidations	2	MAOA, MAOB
Phase I - Functionalization of compounds	2	MAOA, MAOB
Neurotransmitter release cycle	1	MAOA
Neurotransmitter clearance	1	MAOA
Transmission across Chemical Synapses	1	MAOA
Neuronal System	1	MAOA
Cytokine Signaling in Immune system	1	MAOA
Disease	1	MAOA
Immune System	1	MAOA
Norepinephrine Neurotransmitter Release Cycle	1	MAOA
Enzymatic degradation of dopamine by COMT	1	MAOA
Enzymatic degradation of Dopamine by monoamine oxidase	1	MAOA
Dopamine clearance from the synaptic cleft	1	MAOA
Metabolism of serotonin	1	MAOA
Serotonin clearance from the synaptic cleft	1	MAOA
Signaling by Interleukins	1	MAOA
Defective MAOA causes BRUNS	1	MAOA
Metabolic disorders of biological oxidation enzymes	1	MAOA
Diseases of metabolism	1	MAOA
Interleukin-4 and Interleukin-13 signaling	1	MAOA

Dominant GO biological processes

GO term	Targets
dopamine catabolic process	2
biogenic amine metabolic process	1
positive regulation of signal transduction	1
serotonin catabolic process	1
catecholamine metabolic process	1
substantia nigra development	1
hydrogen peroxide biosynthetic process	1

Indications & clinical

Indications

23 indications (5 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
pneumonia	4	MONDO:0005249	EFO:0003106
bacterial infectious disease with sepsis	4	MONDO:0005229	EFO:0003033
osteomyelitis	4	MONDO:0005246	EFO:0003102
bacterial infectious disease	4	MONDO:0005113	EFO:0000771
skin disorder	3	MONDO:0005093	EFO:0000701
pulmonary tuberculosis	3	MONDO:0006052	EFO:1000049
staphylococcus aureus infection	3	MONDO:0005545	EFO:0005681
bacterial pneumonia	3	MONDO:0004652	EFO:1001272
abscess	3	MONDO:0005227	EFO:0003030
cellulitis	3	MONDO:0005230	EFO:0003035
streptococcal pneumonia	3	MONDO:0005972	EFO:1001474
gram-positive bacterial infections	3	MONDO:0021679	MONDO:0021679
Foster-Kennedy syndrome	3	MONDO:0001998	EFO:1001330
syphilis	3	MONDO:0005976	EFO:0007504
tuberculosis	3	MONDO:0018076	MONDO:0018076
multidrug-resistant tuberculosis	2	MONDO:0005861	EFO:0007381
meningitis	2	MONDO:0021108	MONDO:0021108
cystic fibrosis	2	MONDO:0009061	MONDO:0009061
hematopoietic and lymphoid system neoplasm	2	MONDO:0002334	MONDO:0044881
lung disorder	2	MONDO:0005275	EFO:0003818
burn	1	MONDO:0043519	EFO:0009516

2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 132.

Phase distribution

Phase	Trials
PHASE3	37
PHASE2	32
Not specified	26
PHASE4	16
PHASE1	10
PHASE2/PHASE3	7
PHASE1/PHASE2	4

Top trials by phase / activity

NCT	Phase	Status	Title
NCT05398679	PHASE4	RECRUITING	Oral Antimicrobial Treatment vs. Outpatient Parenteral for Infective Endocarditis
NCT05571722	PHASE4	RECRUITING	Linezolid or Vancomycin Surgical Site Infection Prophylaxis
NCT06709196	PHASE4	RECRUITING	Clinical Trial Testing Whether Targeted Antibiotic Prophylaxis Can Reduce Infections After Cystectomy Compared to Empiric Prophylaxis
NCT07301294	PHASE4	NOT_YET_RECRUITING	Microbiological Characteristics of Biofilm on Double J Ureteral Stents After Lithotripsy.
NCT00084266	PHASE4	COMPLETED	Nosocomial Pneumonia With Suspected Or Proven Methicillin-Resistant Staphylococcus Aureus (MRSA)
NCT00087490	PHASE4	COMPLETED	Skin Structure Infections With Suspected or Proven Methicillin-Resistant Staphylococcus Aureus (MRSA)
NCT00147511	PHASE4	COMPLETED	Time To Efficacy and Onset Of Action Of Linezolid
NCT00572559	PHASE4	COMPLETED	Microbiologic Response With Linezolid And Vancomycin In Ventilator-Associated Pneumonia Due To Methicillin Resistant Staphylococcus Aureus
NCT00711854	PHASE4	COMPLETED	Randomized Clinical Trial to Compare a Regimen of Trimethoprim-sulfamethoxazole Plus Rifampicin With a Regimen of Linezolid in the Treatment of Methicillin-Resistant Staphylococcus Aureus (MRSA) Infection
NCT01200654	PHASE4	COMPLETED	Population Pharmacokinetics of Linezolid
NCT01734694	PHASE4	TERMINATED	Safety and Efficacy of Strategy to Prevent Drug-Induced Nephrotoxicity in High-Risk Patients
NCT01805284	PHASE4	COMPLETED	Pharmacokinetic and Pharmacodynamic Evaluation of Linezolid Administered Intravenously in MRSA-positive, Morbidly Obese Patients With Pneumonia
NCT03012360	PHASE4	TERMINATED	Antimicrobial Treatment in Patients With Ventilator-associated Tracheobronchitis
NCT05156437	PHASE4	TERMINATED	Postoperative Antibiotic Management Duration Following Surgery for Intravenous Drug Abuse (IVDA) Endocarditis (OPTIMAL)
NCT05306223	PHASE4	UNKNOWN	A Study of an Oral Short-course Regimen Including Bedaquiline for the Treatment of Participants With Multidrug-resistant Tuberculosis in China
NCT05977868	PHASE4	TERMINATED	Comparing Oral Versus Parenteral Antimicrobial Therapy
NCT04310930	PHASE2/PHASE3	RECRUITING	Finding the Optimal Regimen for Mycobacterium Abscessus Treatment
NCT05069974	PHASE3	ACTIVE_NOT_RECRUITING	Alternative Antibiotics for Syphilis
NCT06081361	PHASE3	ACTIVE_NOT_RECRUITING	Innovating Shorter, All- Oral, Precised, Individualized Treatment Regimen for Rifampicin Resistant Tuberculosis：Contezolid, Delamanid and Bedaquiline Cohort
NCT06441006	PHASE2/PHASE3	RECRUITING	Program for Rifampicin-Resistant Disease With Stratified Medicine for Tuberculosis
NCT06444802	PHASE3	NOT_YET_RECRUITING	Model-informed Precision Dosing for Linezolid
NCT06649721	PHASE3	ACTIVE_NOT_RECRUITING	Innovating Shorter, All- Oral, Precised Treatment Regimen for Rifampicin Resistant Tuberculosis：BDLL Chinese Cohort
NCT00035425	PHASE3	COMPLETED	Treatment of Neutropenic Patients With Fever Who Are Suspected to Have A Gram Positive Infection
NCT00035854	PHASE3	COMPLETED	New Antibiotic to Treat Pediatric Patients With Infections Due to a Specific Bacteria (Vancomycin-Resistant Enterococcus)
NCT00037050	PHASE3	COMPLETED	Antibiotic Treatment for Infections of Short Term In-dwelling Vascular Catheters Due to Gram Positive Bacteria
NCT00150332	PHASE3	COMPLETED	Linezolid for the Treatment of Infections Caused by Methicillin Resistant Staphylococcus Aureus in Japan
NCT00303550	PHASE3	COMPLETED	Study of Intravenous (I.V.) Iclaprim Versus Linezolid in Complicated Skin and Skin Structure Infections [cSSSI] (ASSIST-2)
NCT00852540	PHASE3	COMPLETED	Retapamulin Versus Linezolid in the Treatment of SITL and Impetigo Due to MRSA
NCT00865280	PHASE3	TERMINATED	Study the Safety and Efficacy of PTK 0796 in Patients With Complicated Skin and Skin Structure Infection (CSSSI)
NCT00876850	PHASE3	WITHDRAWN	Phase 3 Study - Safety and Efficacy of PTK 0796 in Patients With Complicated Skin and Skin Structure Infection (CSSSI)
NCT01170221	PHASE3	COMPLETED	TR-701 FA vs. Linezolid for the Treatment of Acute Bacterial Skin and Skin Structure Infections.
NCT01339091	PHASE3	COMPLETED	Efficacy and Safety of Dalbavancin for the Treatment of Acute Bacterial Skin and Skin Structure Infections
NCT01421511	PHASE3	COMPLETED	TR-701 FA vs Linezolid for the Treatment of Acute Bacterial Skin and Skin Structure Infections
NCT01431339	PHASE3	COMPLETED	Efficacy and Safety of Dalbavancin for the Treatment of Acute Bacterial Skin and Skin Structure Infections
NCT01792804	PHASE3	COMPLETED	Staphylococcus Aureus Bacteremia Antibiotic Treatment Options
NCT01967225	PHASE3	COMPLETED	Safety and Efficacy of BAY1192631 in Japanese Patients With Methicillin-resistant Staphylococcus Aureus (MRSA) Infections
NCT02019420	PHASE3	COMPLETED	Tedizolid Phosphate (TR-701 FA, MK-1986) vs Linezolid for the Treatment of Nosocomial Pneumonia (MK-1986-002)
NCT02066402	PHASE3	COMPLETED	Efficacy and Safety of Intravenous to Oral 6-Day Tedizolid Phosphate vs. Intravenous to Oral 10-Day Linezolid in Patients With Acute Bacterial Skin and Skin Structure Infection (ABSSSI)
NCT02269644	PHASE3	WITHDRAWN	A P3 Comparator Trial in Community Acquired Bacterial Pneumonia
NCT02333799	PHASE3	COMPLETED	A Phase 3 Trial Assessing Safety and Efficacy of B-Pa-L in Participants With DR-TB

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

174 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
TEDIZOLID	ChEMBL + PubChem	Phase 4 (approved)	MAOA, MAOB
CLOTRIMAZOLE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
DANTHRON	ChEMBL	Phase 4 (approved)	MAOA, MAOB
FENTANYL	ChEMBL	Phase 4 (approved)	MAOA, MAOB
IPRONIAZID	ChEMBL	Phase 4 (approved)	MAOA, MAOB
MENADIONE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
METHYLENE BLUE CATION	ChEMBL	Phase 4 (approved)	MAOA, MAOB
MICONAZOLE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
MOCLOBEMIDE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
PARGYLINE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
PHENELZINE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
PIOGLITAZONE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
PRIMAQUINE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
RASAGILINE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
ROSIGLITAZONE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
SAFINAMIDE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
SELEGILINE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
TOLOXATONE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
TRANYLCYPROMINE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
TROGLITAZONE	ChEMBL	Phase 4 (approved)	MAOA, MAOB
CURCUMIN	ChEMBL	Phase 3	MAOA, MAOB
IDAZOXAN	ChEMBL	Phase 3	MAOA, MAOB
QUERCETIN	ChEMBL	Phase 3	MAOA, MAOB
RESVERATROL	ChEMBL	Phase 3	MAOA, MAOB
BROFAROMINE	ChEMBL	Phase 2	MAOA, MAOB
CIGLITAZONE	ChEMBL	Phase 2	MAOA, MAOB
CLORGILINE	ChEMBL	Phase 2	MAOA, MAOB
DAIDZEIN	ChEMBL	Phase 2	MAOA, MAOB
FORMONONETIN	ChEMBL	Phase 2	MAOA, MAOB
GENISTEIN	ChEMBL	Phase 2	MAOA, MAOB
LADOSTIGIL	ChEMBL	Phase 2	MAOA, MAOB
LUTEOLIN	ChEMBL	Phase 2	MAOA, MAOB
MOFEGILINE	ChEMBL	Phase 2	MAOA, MAOB
PHENAMAZOLINE	ChEMBL	Phase 2	MAOA, MAOB
PIPERINE	ChEMBL	Phase 2	MAOA, MAOB
SEMBRAGILINE	ChEMBL	Phase 2	MAOA, MAOB
SUTEZOLID	ChEMBL	Phase 2	MAOA, MAOB
TIOXOLONE	ChEMBL	Phase 2	MAOA, MAOB
CRIZOTINIB	ChEMBL + PubChem	Phase 4 (approved)	MAOA
REGORAFENIB	ChEMBL + PubChem	Phase 4 (approved)	MAOA
TAFAMIDIS	ChEMBL + PubChem	Phase 4 (approved)	MAOA
ABROCITINIB	ChEMBL	Phase 4 (approved)	MAOA
AMILORIDE	ChEMBL	Phase 4 (approved)	MAOA
ANISINDIONE	ChEMBL	Phase 4 (approved)	MAOA
ARIPIPRAZOLE	ChEMBL	Phase 4 (approved)	MAOA
ATALUREN	ChEMBL	Phase 4 (approved)	MAOA
BENOXAPROFEN	ChEMBL	Phase 4 (approved)	MAOA
BIFONAZOLE	ChEMBL	Phase 4 (approved)	MAOA
CABOZANTINIB	ChEMBL	Phase 4 (approved)	MAOA
CHLOROPROCAINE	ChEMBL	Phase 4 (approved)	MAOA
COCAINE	ChEMBL	Phase 4 (approved)	MAOA
DEBRISOQUIN	ChEMBL	Phase 4 (approved)	MAOA
DELAVIRDINE	ChEMBL	Phase 4 (approved)	MAOA
DEQUALINIUM	ChEMBL	Phase 4 (approved)	MAOA
DEXTROAMPHETAMINE	ChEMBL	Phase 4 (approved)	MAOA
DISULFIRAM	ChEMBL	Phase 4 (approved)	MAOA
DONEPEZIL	ChEMBL	Phase 4 (approved)	MAOB
ETHOPROPAZINE	ChEMBL	Phase 4 (approved)	MAOA
ETHYNODIOL DIACETATE	ChEMBL	Phase 4 (approved)	MAOA
FAMOTIDINE	ChEMBL	Phase 4 (approved)	MAOA