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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 15:46:59 UTC
HMDB IDHMDB0014739
Secondary Accession Numbers
  • HMDB14739
Metabolite Identification
Common NameLinezolid
DescriptionLinezolid 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.
Structure
Data?1582753215
Synonyms
ValueSource
N-(((S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl)methyl)acetamideChEBI
ZyvoxKegg
N-((3-(3-Fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl)methyl)acetamideHMDB
LinezolideHMDB
Chemical FormulaC16H20FN3O4
Average Molecular Weight337.3461
Monoisotopic Molecular Weight337.143784348
IUPAC NameN-{[(5S)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide
Traditional Namelinezolid
CAS Registry Number165800-03-3
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 KeyTYZROVQLWOKYKF-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxazinanes
Sub ClassMorpholines
Direct ParentPhenylmorpholines
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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.44 g/LNot Available
LogP0.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.44 g/LALOGPS
logP10(0.61) g/LALOGPS
logP10(0.64) g/LChemAxon
logS10(-2.4) g/LALOGPS
pKa (Strongest Acidic)14.45ChemAxon
pKa (Strongest Basic)-0.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.11 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity84.47 m³·mol⁻¹ChemAxon
Polarizability34.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+173.44130932474
DeepCCS[M-H]-171.04130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LinezolidCC(=O)NC[C@H]1CN(C(=O)O1)C1=CC(F)=C(C=C1)N1CCOCC13525.9Standard polar33892256
LinezolidCC(=O)NC[C@H]1CN(C(=O)O1)C1=CC(F)=C(C=C1)N1CCOCC12876.9Standard non polar33892256
LinezolidCC(=O)NC[C@H]1CN(C(=O)O1)C1=CC(F)=C(C=C1)N1CCOCC13237.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Linezolid,1TMS,isomer #1CC(=O)N(C[C@H]1CN(C2=CC=C(N3CCOCC3)C(F)=C2)C(=O)O1)[Si](C)(C)C2895.6Semi standard non polar33892256
Linezolid,1TMS,isomer #1CC(=O)N(C[C@H]1CN(C2=CC=C(N3CCOCC3)C(F)=C2)C(=O)O1)[Si](C)(C)C2681.9Standard non polar33892256
Linezolid,1TMS,isomer #1CC(=O)N(C[C@H]1CN(C2=CC=C(N3CCOCC3)C(F)=C2)C(=O)O1)[Si](C)(C)C3772.9Standard polar33892256
Linezolid,1TBDMS,isomer #1CC(=O)N(C[C@H]1CN(C2=CC=C(N3CCOCC3)C(F)=C2)C(=O)O1)[Si](C)(C)C(C)(C)C3100.3Semi standard non polar33892256
Linezolid,1TBDMS,isomer #1CC(=O)N(C[C@H]1CN(C2=CC=C(N3CCOCC3)C(F)=C2)C(=O)O1)[Si](C)(C)C(C)(C)C2941.0Standard non polar33892256
Linezolid,1TBDMS,isomer #1CC(=O)N(C[C@H]1CN(C2=CC=C(N3CCOCC3)C(F)=C2)C(=O)O1)[Si](C)(C)C(C)(C)C3835.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Linezolid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-4292000000-5170fb56647608eed4302017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Linezolid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Linezolid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid LC-ESI-QFT , positive-QTOFsplash10-000i-0009000000-05a0d0b23e80851df1d52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid LC-ESI-QFT , positive-QTOFsplash10-000j-0396000000-959c643931df034e05fc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid LC-ESI-QFT , positive-QTOFsplash10-000b-0940000000-066fc762e228726946fb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid LC-ESI-QFT , positive-QTOFsplash10-0292-0900000000-99847141a31b0134dcfa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid LC-ESI-QFT , positive-QTOFsplash10-000j-0900000000-7cf676c358a3890ab4602017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid LC-ESI-QFT , positive-QTOFsplash10-000j-0900000000-fdccf108eb9fcb8a102d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid , positive-QTOFsplash10-000i-1649000000-a1dedd5c256e9f3bfa4f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid , positive-QTOFsplash10-000i-0649000000-1ac199ac8af65a2644f82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid 35V, Positive-QTOFsplash10-000j-0972000000-f92653e1d91ee8543bb42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid 45V, Positive-QTOFsplash10-000b-0940000000-0711d88ecca97721cf7e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid 35V, Negative-QTOFsplash10-008b-4090000000-c3f9f9dd9eae71988eba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid 60V, Positive-QTOFsplash10-0292-0900000000-1570ab964080c874de432021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid 30V, Positive-QTOFsplash10-000j-0297000000-73173bf0292e65c168412021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid 15V, Positive-QTOFsplash10-000i-0009000000-8562c06c8dcd0b4893cf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Linezolid 75V, Positive-QTOFsplash10-000j-0900000000-79bb52e95431285441272021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linezolid 10V, Positive-QTOFsplash10-000f-0095000000-3ebea74048f88df3cb4a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linezolid 20V, Positive-QTOFsplash10-0006-0090000000-96eb6763b5a2a907e2f12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linezolid 40V, Positive-QTOFsplash10-053r-9860000000-947b5be602b12bd9b78f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linezolid 10V, Negative-QTOFsplash10-000l-2179000000-12bfdea8c4c5e2b1143e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linezolid 20V, Negative-QTOFsplash10-0arc-9283000000-ab9a9e6dc95bc68ff6c32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linezolid 40V, Negative-QTOFsplash10-0btc-9740000000-4ca38bd856baf42e41792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linezolid 10V, Positive-QTOFsplash10-000i-0009000000-15a1e52af5b01e4259432021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linezolid 20V, Positive-QTOFsplash10-004i-0091000000-cc6595bff24fbc8c17272021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linezolid 40V, Positive-QTOFsplash10-0k96-3490000000-fdd909ee5e5fd9c996512021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Linezolid 10V, Negative-QTOFsplash10-000i-3019000000-024547f1b0b65495d5a42021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00601 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00601 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00601
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID390139
KEGG Compound IDC08146
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLinezolid
METLIN IDNot Available
PubChem Compound441401
PDB IDZLD
ChEBI ID63607
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Park IN, Hong SB, Oh YM, Kim MN, Lim CM, Lee SD, Koh Y, Kim WS, Kim DS, Kim WD, Shim TS: Efficacy and tolerability of daily-half dose linezolid in patients with intractable multidrug-resistant tuberculosis. J Antimicrob Chemother. 2006 Sep;58(3):701-4. Epub 2006 Jul 19. [PubMed:16857689 ]
  2. South African Electronic Package Inserts [Link]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
References
  1. Stevens DL, Dotter B, Madaras-Kelly K: A review of linezolid: the first oxazolidinone antibiotic. Expert Rev Anti Infect Ther. 2004 Feb;2(1):51-9. [PubMed:15482171 ]
  2. Taylor JJ, Wilson JW, Estes LL: Linezolid and serotonergic drug interactions: a retrospective survey. Clin Infect Dis. 2006 Jul 15;43(2):180-7. Epub 2006 Jun 9. [PubMed:16779744 ]
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
References
  1. Stevens DL, Dotter B, Madaras-Kelly K: A review of linezolid: the first oxazolidinone antibiotic. Expert Rev Anti Infect Ther. 2004 Feb;2(1):51-9. [PubMed:15482171 ]
  2. Taylor JJ, Wilson JW, Estes LL: Linezolid and serotonergic drug interactions: a retrospective survey. Clin Infect Dis. 2006 Jul 15;43(2):180-7. Epub 2006 Jun 9. [PubMed:16779744 ]