EPEREZOLID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H23FN4O5
Molecular Weight	394.3974
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC=C(N3CCN(CC3)C(=O)CO)C(F)=C2

InChI

InChIKey=SIMWTRCFFSTNMG-AWEZNQCLSA-N

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

HIDE SMILES / InChI

Molecular Formula	C18H23FN4O5
Molecular Weight	394.3974
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9333036
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8834904

Eperezolid is an antibiotic agent developed for the treatment of a wide range of bacterial infections. The drug exerts its action by binding to 50 S ribosome subunit causing the inhibition of protein synthesis in bacterias. Eperezolid was tested in preclinical in vivo models of different becterial diseases in which it was shown to be active.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 180 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9333036	Binding Agent 1076		20.0 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10582874	Curative		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Pharmacokinetics of Linezolid and Ertapenem in experimental parapneumonic pleural effusion.	2010-05-18	20482752
Production of icaADBC-encoded polysaccharide intercellular adhesin and therapeutic failure in pediatric patients with Staphylococcal device-related infections.	2010-03-15	20230642
Clinical outcomes of antimicrobial lock solutions used in a treatment modality: a retrospective case series analysis.	2010	22291495
Synthesis and antibacterial activities of eperezolid analogs with glycinyl substitutions.	2009-07	19544480
Synthesis and in vitro antibacterial activity of novel methylamino piperidinyl oxazolidinones.	2007-09-15	17624776
High-performance liquid chromatographic method for simple and rapid determination of linezolid in human plasma.	2006-08	16292746
Synthesis and SAR of novel oxazolidinones: discovery of ranbezolid.	2005-10-01	16054358
Synthesis and antibacterial activity of dihydro-1,2-oxazine and 2-pyrazoline oxazolidinones: novel analogs of linezolid.	2005-06-02	15911264
In vitro activity of vancomycin, quinupristin/dalfopristin, and linezolid against intact and disrupted biofilms of staphylococci.	2005-01-07	15638934
Simple method for the assay of eperezolid in brain heart infusion broth by high-performance liquid chromatography.	2004-06-29	15193729
Simple method for the assay of linezolid in Brain Heart Infusion broth by high-performance liquid chromatography.	2004-01	14872541
Oxazolidinone antibacterial agents: a critical review.	2003	12678835
Carbon-carbon-linked (pyrazolylphenyl)oxazolidinones with antibacterial activity against multiple drug resistant gram-positive and fastidious gram-negative bacteria.	2001-12	11711300
The discovery of linezolid, the first oxazolidinone antibacterial agent.	2001-08	12455414
Novel piperidinyloxy oxazolidinone antimicrobial agents.	2001-07-23	11459641
RU-79115 (Aventis Pharma).	2001-06	11572652
Oxazolidinones: a review.	2000-01	10718097
Activities of several novel oxazolidinones against Mycobacterium tuberculosis in a murine model.	1999-05	10223934
In vitro activities of U-100592 and U-100766, novel oxazolidinone antibacterial agents.	1996-04	8849237
Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant gram-positive bacterial infections.	1996-02-02	8576909

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Eperezolide was active against all classes of pneumococci, with MIC90s of 0.5 ug/ml.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:02:43 GMT 2025` Edited by `admin` on `Mon Mar 31 18:02:43 GMT 2025`
Record UNII	C460ZSU1OW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPEREZOLID

Official Name

English

U-100,592

Preferred Name

English

Eperezolid [WHO-DD]

Common Name

English

U-100592

Code

English

eperezolid [INN]

Common Name

English

ACETAMIDE, N-((3-(3-FLUORO-4-(4-(HYDROXYACETYL)-1-PIPERAZINYL)PHENYL)-2-OXO-5-OXAZOLIDINYL)METHYL)-, (S)-

Common Name

English

EPEREZOLID [USAN]

Common Name

English

N-[[(S)-3-[3-fluoro-4-(4-glycoloyl-1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C258