Chemical Component Summary

NameN-{[(5S)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide
SynonymsLinezolid
IdentifiersN-[[(5S)-3-(3-fluoro-4-morpholin-4-yl-phenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]ethanamide
FormulaC16 H20 F N3 O4
Molecular Weight337.346
TypeNON-POLYMER
Isomeric SMILESCC(=O)NC[C@H]1CN(C(=O)O1)c2ccc(c(c2)F)N3CCOCC3
InChIInChI=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
InChIKeyTYZROVQLWOKYKF-ZDUSSCGKSA-N

Chemical Details

Formal Charge0
Atom Count44
Chiral Atom Count1
Bond Count46
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB00601 
NameLinezolid
Groups
  • approved
  • investigational
DescriptionLinezolid is a synthetic antibiotic which is used for the treatment of infections caused by aerobic Gram-positive bacteria. Its effects are bacteriostatic against both enterococci and staphylococci and bactericidal against most isolates of streptococci.[L32965] Linezolid exerts its antibacterial activity by inhibiting the initiation of bacterial protein synthesis - more specifically, it binds to the 23S ribosomal RNA of the 50S subunit[A11227,A199050] and, in doing so, prevents the formation of the 70S initiation complex which is essential for bacterial reproduction. Linezolid was initially approved in 2000 and was the first member of the oxazolidinone antibiotic class.[A233425] A second member of this class, [tedizolid], was approved by the FDA in 2014 and is considered generally more effective and tolerable than its predecessor.
Synonyms
  • Linezolide
  • Linezolid
  • Linezolidum
  • N-(((S)-3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide
Brand Names
  • Linezolid Tablets
  • Linezolid Intravenous Injection
  • Linezolid Injection
  • Jamp Linezolid
  • Sandoz Linezolid
IndicationLinezolid is indicated in adults and children for the treatment of infections caused by susceptible Gram-positive bacteria, including nosocomial pneumonia, community-acquired pneumonia, skin and skin structure infections, and vancomycin-resistant _Enterococcus faecium_ infections.[L32965] Examples of susceptible bacteria include _Staphylococcus aureus_, _Streptococcus pneumoniae_, _Streptococcus pyogenes_, and _Streptococcus agalactiae_.[L32965] Linezolid is not indicated for the treatment of Gram-negative infections, nor has it been evaluated for use longer than 28 days.[L32965]
Categories
  • Acetamides
  • Acetates
  • Acids, Acyclic
  • Agents that produce hypertension
  • Agents that reduce seizure threshold
ATC-CodeJ01XX08
CAS number165800-03-3

Drug Targets

NameTarget SequencePharmacological ActionActions
23S ribosomal RNA-unknowninhibitor
Amine oxidase [flavin-containing] BMSNKCDVVVVGGGISGMAAAKLLHDSGLNVVVLEARDRVGGRTYTLRNQK...unknowninhibitor
Amine oxidase [flavin-containing] AMENQEKASIAGHMFDVVVIGGGISGLSAAKLLTEYGVSVLVLEARDRVGG...unknowninhibitor
Serum albuminMKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...unknownbinder
Solute carrier family 22 member 6MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 441401
ChEMBL CHEMBL126
ChEBI CHEBI:63607
CCDC/CSD TIYQAU01, QUGNEO, QUGNUE, QUGNIS, TIYQAU, TIYQAU02
COD 2108674, 2108676, 2108678