Compound ID | 757

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Eperezolid

Synonym(s): PNU 100592  |  U 100592  |  U100592  |  (S)-N-[[3-[3-fluoro-4-[4-(hydroxyacetyl)-1-piperazinyl]- phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide

Class: Oxazolidinone

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Protein synthesis inhibitor. Binds to the 50S ribosomal subunit
Description: A fluorinated oxazolidinone; Pawsey SD, Harry JD, Stalker DJ. 1st administration of a new oxazolidinone antibiotic (U-100592) to man. 35th-ICAAC 1995;15
Institute where first reported: Pharmacia & Upjohn (Pfizer, USA)
Year first mentioned: 1995
Highest development stage: Phase 3
Development status: Inactive
Reason dropped: Less effective than linezolid; development of resistance observed
Chemical structure(s):
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Molecular weight: 394.4
Iso. SMILES: CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCN(CC3)C(=O)CO)F
InChI Key: SIMWTRCFFSTNMG-AWEZNQCLSA-N
Can. SMILES: CC(=O)NC[C@H]1CN(C2=CC=C(C(=C2)F)N3CCN(CC3)C(=O)CO)C(=O)O1
InChI: InChI=1S/C18H23FN4O5/c1-12(25)20-9-14-10-23(18(27)28-14)13-2-3-16(15(19)8-13)21-4-6-22(7-5-21)17(26)11-24/h2-3,8,14,24H,4-7,9-11H2,1H3,(H,20,25)/t14-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/73214
Guide to Pharmacology: eperezolid
Citations:
  • https://doi.org/10.1016/s0140-6736(01)06964-1
  • https://doi.org/10.1021/jm9509556
  • https://doi.org/10.1128/aac.40.4.839
  • https://doi.org/10.1128/aac.40.3.720

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