SynCED: Linezolid

Record Information

Version

1.0

Creation Date

2009-07-15 20:47:03 UTC

Update Date

2026-05-14 16:43:40 UTC

Accession Number

CHEM002120

Identification

Common Name

Linezolid

Class

Small Molecule

Description

Linezolid is only found in individuals that have used or taken this drug. It is a synthetic antibiotic, the first of the oxazolidinone class, used for the treatment of infections caused by multi-resistant bacteria including streptococcus and methicillin-resistant Staphylococcus aureus (MRSA). Linezolid is a synthetic antibacterial agent of the oxazolidinone class of antibiotics. It has in vitro activity against aerobic Gram positive bacteria, certain Gram negative bacteria and anaerobic microorganisms. It selectively inhibits bacterial protein synthesis through binding to sites on the bacterial ribosome and prevents the formation of a functional 70S-initiation complex. Specifically, linezolid binds to a site on the bacterial 23S ribosomal RNA of the 50S subunit and prevents the formation of a functional 70S initiation complex, which is an essential component of the bacterial translation process. The results of time-kill studies have shown linezolid to be bacteriostatic against enterococci and staphylococci. For streptococci, linezolid was found to be bactericidal for the majority of strains. Linezolid is also a reversible, nonselective inhibitor of monoamine oxidase. Therefore, linezolid has the potential for interaction with adrenergic and serotonergic agents.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Anti-Bacterial Agent
Anti-Infective Agent
Drug
Ester
Ether
Human Neurotoxin
Metabolite
Organic Compound
Organofluoride
Protein Synthesis Inhibitor
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-(((S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide	ChEBI
Zyvox	Kegg
N-((3-(3-Fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide	HMDB
Linezolide	HMDB

Chemical Formula

C₁₆H₂₀FN₃O₄

Average Molecular Mass

337.346 g/mol

Monoisotopic Mass

337.144 g/mol

CAS Registry Number

165800-03-3

IUPAC Name

N-{[(5S)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide

Traditional Name

linezolid

SMILES

CC(=O)NC[C@H]1CN(C(=O)O1)C1=CC(F)=C(C=C1)N1CCOCC1

InChI Identifier

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

InChI Key

TYZROVQLWOKYKF-ZDUSSCGKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxazinanes

Sub Class

Morpholines

Direct Parent

Phenylmorpholines

Alternative Parents

Substituents

Phenylmorpholine
Aniline or substituted anilines
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Fluorobenzene
Halobenzene
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Oxazolidinone
Benzenoid
Oxazolidine
Acetamide
Carbamic acid ester
Secondary carboxylic acid amide
Tertiary amine
Amino acid or derivatives
Carboxamide group
Carbonic acid derivative
Azacycle
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Ether
Amine
Organic oxide
Hydrocarbon derivative
Organohalogen compound
Organofluoride
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:63607 )
acetamides (CHEBI:63607 )
morpholines (CHEBI:63607 )
oxazolidinone (CHEBI:63607 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Bone Marrow
Eyes
Nerve Cells

Pathways

Not Available

Applications

antibacterial drug

Biological Roles

Chemical Roles

protein synthesis inhibitor

Physical Properties

State

Solid

Appearance

Whitish crystalline powder (MSDS, A308).

Experimental Properties

Property	Value
Melting Point	182°C
Boiling Point	Not Available
Solubility	3 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	1.44 g/L	ALOGPS
logP	0.61	ALOGPS
logP	0.64	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	14.45	ChemAxon
pKa (Strongest Basic)	-0.66	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.11 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.47 m³·mol⁻¹	ChemAxon
Polarizability	34.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Toxicity Profile

Route of Exposure

Inhalation (MSDS). Linezolid is rapidly and extensively absorbed after oral dosing. Maximum plasma concentrations are reached approximately 1 to 2 hours after dosing, and the absolute bioavailability is approximately 100%.

Mechanism of Toxicity

Linezolid targets the large 39S subunit of the mitochondrial ribosome thereby deactivation mitochondrial protein synthesis. As a result Linezolid is cytotoxic to the most metabolically active cells or tissues including the heart, liver, thymus and bone-marrow. (3). The likely target of Linezolid is the 16S rRNA molecule in the mitochondrial ribosome, which is analogous to the 23S rRNA in bacterial ribosomes.

Metabolism

Linezolid is rapidly and extensively absorbed after oral dosing. Maximum plasma concentrations are reached approximately 1 to 2 hours after dosing, and the absolute bioavailability is approximately 100%. Linezolid is primarily metabolized by oxidation of the morpholine ring, which results in two inactive ring-opened carboxylic acid metabolites: the aminoethoxyacetic acid metabolite (A), and the hydroxyethyl glycine metabolite (1). Half Life: 4.5-5.5 hours.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of bacterial infections caused by susceptible strains of vancomycin resistant Enterococcus faecium, Staphylococcal aureus (methicillin resistant and susceptible strains), Streptococcus pneumoniae, Streptococcus pyogenes, Streptococcus agalactiae (1).

Minimum Risk Level

Not Available

Health Effects

Common adverse effects of short-term use include headache, diarrhea, and nausea. Long-term use, however, has been associated with serious adverse effects; linezolid can cause bone marrow suppression and low platelet counts, particularly when used for more than two weeks. If used for longer periods still, it may cause sometimes irreversible chemotherapy-induced peripheral neuropathy and optic nerve damage, and lactic acidosis (a buildup of lactic acid in the body), all most likely due to mitochondrial toxicity.

Symptoms

Clinical signs of acute toxicity lead to decreased activity, ataxia, vomiting and tremors.

Treatment

Drug therapy is discontinued immediately; exchange transfusion may be required to remove the drug. Sometimes, phenobarbital (UGT induction) is used.

Concentrations

Not Available

External Links

DrugBank ID

DB00601

HMDB ID

HMDB0014739

FooDB ID