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 179 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9333036	Binding Agent 1064		20.0 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10582874	Curative		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
In vitro activities of U-100592 and U-100766, novel oxazolidinone antibacterial agents.	1996 Apr	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 Feb 2	8576909
Activities of several novel oxazolidinones against Mycobacterium tuberculosis in a murine model.	1999 May	10223934
Oxazolidinones: a review.	2000 Jan	10718097
The discovery of linezolid, the first oxazolidinone antibacterial agent.	2001 Aug	12455414
Carbon-carbon-linked (pyrazolylphenyl)oxazolidinones with antibacterial activity against multiple drug resistant gram-positive and fastidious gram-negative bacteria.	2001 Dec	11711300
Novel piperidinyloxy oxazolidinone antimicrobial agents.	2001 Jul 23	11459641
RU-79115 (Aventis Pharma).	2001 Jun	11572652
Oxazolidinone antibacterial agents: a critical review.	2003	12678835
Simple method for the assay of linezolid in Brain Heart Infusion broth by high-performance liquid chromatography.	2004 Jan	14872541
Simple method for the assay of eperezolid in brain heart infusion broth by high-performance liquid chromatography.	2004 Jun 29	15193729
In vitro activity of vancomycin, quinupristin/dalfopristin, and linezolid against intact and disrupted biofilms of staphylococci.	2005 Jan 7	15638934
Synthesis and antibacterial activity of dihydro-1,2-oxazine and 2-pyrazoline oxazolidinones: novel analogs of linezolid.	2005 Jun 2	15911264
Synthesis and SAR of novel oxazolidinones: discovery of ranbezolid.	2005 Oct 1	16054358
High-performance liquid chromatographic method for simple and rapid determination of linezolid in human plasma.	2006 Aug	16292746
Synthesis and in vitro antibacterial activity of novel methylamino piperidinyl oxazolidinones.	2007 Sep 15	17624776
Synthesis and antibacterial activities of eperezolid analogs with glycinyl substitutions.	2009 Jul	19544480
Clinical outcomes of antimicrobial lock solutions used in a treatment modality: a retrospective case series analysis.	2010	22291495
Production of icaADBC-encoded polysaccharide intercellular adhesin and therapeutic failure in pediatric patients with Staphylococcal device-related infections.	2010 Mar 15	20230642
Pharmacokinetics of Linezolid and Ertapenem in experimental parapneumonic pleural effusion.	2010 May 18	20482752

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 `Fri Dec 15 15:36:20 UTC 2023` Edited by `admin` on `Fri Dec 15 15:36:20 UTC 2023`
Record UNII	C460ZSU1OW
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

EPEREZOLID

Official Name

English

Eperezolid [WHO-DD]

Common Name

English

U-100,592

Code

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