856677-03-7

Usage

Uses

Used in Pharmaceutical Industry:
Linezolid is used as an antibiotic for the treatment of certain bacterial infections, particularly those caused by gram-positive bacteria. Its application is primarily for skin and soft tissue infections, as well as specific types of pneumonia. The drug's effectiveness against antibiotic-resistant bacteria, such as MRSA and VRE, makes it a valuable asset in the fight against bacterial infections.
Additionally, Linezolid is used as a last-resort antibiotic when other conventional treatments have failed or are not suitable due to drug resistance or patient intolerance. Its versatility in administration, being available in both oral and intravenous forms, contributes to its widespread use in the medical field.

Upstream product

• 1032827-78-3 (S)-2-((3-(4-bromo-3-fluorophenyl)-2-oxooxazolidin-5-yl)methyl)isoindoline-1,3-dione 
• 656-65-5 3-fluoro-4-bromophenylamine 
• 510729-01-8 (4-bromo-3-fluorophenyl)carbamic acid benzyl ester 
• 856676-99-8 methanesulfonic acid (5R)-3-(4-bromo-3-fluorophenyl)-2-oxooxazolidin-5-ylmethyl ester 
• 856677-01-5 (R)-5-(azidomethyl)-3-(4-bromo-3-fluorophenyl)oxazolidin-2-one 
• 1032827-77-2 2-((R)-3-(4-bromo-3-fluorophenylamino)-2-hydroxypropyl)isoindolin-1,3-dione 
• 444335-16-4 (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one 
• 444335-17-5 3-Nitro-benzenesulfonic acid (R)-3-(4-bromo-3-fluoro-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester 

Downstream Products

• 856677-05-9 (5S)-N-[[3-(3-fluoro-4-bromophenyl)-2-oxo-oxazolidin-5-yl]methyl]acetamide 
• 1401342-10-6 C₂₁H₂₁FN₆O₄ 
• 1401342-11-7 C₂₀H₂₁FN₆O₃*ClH 
• 1401342-12-8 C₂₂H₂₃FN₆O₅ 
• 1401342-13-9 C₂₃H₂₃FN₆O₃ 
• 1401342-14-0 C₂₂H₂₅FN₆O₃ 
• 504437-66-5 (S)‐N‐((3‐(3‐fluoro‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenyl)‐2‐oxooxazolidin‐5‐yl)methyl)acetamide 
• 1401341-59-0 C₂₁H₂₁FN₆O₄ 
• 1401341-60-3 C₂₀H₂₁FN₆O₃*ClH 
• 1401341-61-4 C₂₁H₂₃FN₆O₃ 
• 1401341-63-6 C₂₄H₂₇FN₆O₅ 
• 1401341-64-7 C₂₂H₂₅FN₆O₄ 
• 1401341-65-8 C₂₃H₂₅FN₆O₃ 
• 1401341-66-9 C₂₃H₂₃FN₆O₃ 

Relevant academic research and scientific papers

OXAZOLIDINONE COMPOUNDS, LIPOSOME COMPOSITIONS COMPRISING OXAZOLIDINONE COMPOUNDS AND METHOD OF USE THEREOF

Compositions and methods for the treatment of tuberculosis, as well as other mycobacterial and gram positive bacterial infections are disclosed. These compositions contain a highly potent and selective oxazolidinone encapsulated with high efficiency to maximize dosing potential of low toxicity drugs, and are stable in the presence of plasma. The compositions are long circulating and retain their encapsulated drug while in the circulation following intravenous dosing to allow for efficient accumulation at the site of the bacterial or mycobacterial infection. The high doses that can be achieved when combined with the long circulating properties and highly stable retention of the drug allow for a reduced frequency of administration when compared to daily or twice daily administrations of other drugs typically utilized to treat these infections.

Compound design guidelines for evading the efflux and permeation barriers of Escherichia coli with the oxazolidinone class of antibacterials: Test case for a general approach to improving whole cell Gram-negative activity

Previously we reported the results from an effort to improve Gram-negative antibacterial activity in the oxazolidinone class of antibiotics via a systematic medicinal chemistry campaign focused entirely on C-ring modifications. In that series we set about testing if the efflux and permeation barriers intrinsic to the outer membrane of Escherichia coli could be rationally overcome by designing analogs to reside in specific property limits associated with Gram-negative activity: i) low MW (7.4 1), and iii) zwitterionic character at pH 7.4. Indeed, we observed that only analogs residing within these limits were able to overcome these barriers. Herein we report the results from a parallel effort where we explored structural changes throughout all three rings in the scaffold for the same purpose. Compounds were tested against a diagnostic MIC panel of Escherichia coli and Staphylococcus aureus strains to determine the impact of combining structural modifications in overcoming the OM barriers and in bridging the potency gap between the species. The results demonstrated that distributing the charge-carrying moieties across two rings was also beneficial for avoidance of the outer membrane barriers. Importantly, analysis of the structure-permeation relationship (SPR) obtained from this and the prior study indicated that in addition to MW, polarity, and zwitterionic character, having ≤4 rotatable bonds is also associated with evasion of the OM barriers. These combined results provide the medicinal chemist with a framework and strategy for overcoming the OM barriers in GNB in antibacterial drug discovery efforts.

OXAZOLIDINONE COMPOUNDS AND METHODS OF USE THEREOF AS ANTIBACTERIAL AGENTS

The present invention relates to oxazolidinone compounds of Formula (I): and pharmaceutically acceptable salts thereof, wherein A, E, and R1 are as defined herein. The present invention also relates to compositions which comprise at least one oxazolidinone compound of the invention. The invention also provides methods for inhibiting growth of mycobacterial cells as well as a method of treating mycobacterial infections by Mycobacterium tuberculosiscomprising administering a therapeutically effective amount of an oxazolidinone of the invention and/or apharmaceutically acceptable salt thereof, or a composition comprising such compound and/or salt.

Oxazolidinone-quinolone hybrid antibiotics

The present invention relates to compounds of the Formula (I) that are useful antimicrobial agents and effective against a variety of multi-drug resistant bacteria:

NOVEL OXAZOLIDINONE DERIVATIVE AND MEDICAL COMPOSITION CONTAINING SAME

Disclosed is a novel oxazolidinone derivative represented by Formula 1 above, in particular, a novel oxazolidinone compound having a cyclic amidoxime or cyclic amidrazone group. In Formula 1, R and Q are the same as defined in the detailed description. In addition, disclosed is a pharmaceutical composition for an antibiotic which includes the novel oxazolidinone derivative of Formula 1, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an active ingredient. The novel oxazolidinone derivative, the prodrug thereof, the hydrate thereof, the solvate thereof, the isomer thereof, and the pharmaceutically acceptable salt thereof have broad antibacterial spectrum against resistant bacteria, low toxicity and strong antibacterial effects against Gram-positive and Gram-negative bacteria and thus may be effectively used as antibiotics.

NOVEL OXAZOLIDINONE DERIVATIVES, PROCESS FOR PREPARING THEREOF AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME

The present invention relates to a novel oxazolidinone derivative, its prodrugs, hydrates, solvates, isomers, pharmaceutically permitted salts, and its preparation methods and pharmaceutical compositions containing the same. The oxazolidinone derivative and its pharmaceutically permitted salts according to the present invention have wide antimicrobial spectrum against resistant bacteria and low toxicity, and they show strong antibacterial effect against gram-positive and gram-negative pathogens. So, they can be used as good antibiotics.

Novel oxazolidinone-quinolone hybrid antimicrobials

Antimicrobial compounds incorporating oxazolidinone and quinolone pharmacophore substructures have been synthesized and evaluated. Representative analogues 2, 5, and 6 display an improved potency versus linezolid against gram-positive and fastidious gram-negative pathogens. The compounds are also active against linezolid- and ciprofloxacin-resistant Staphylococcus aureus and Enterococcus faecium strains. The MOA for these new antimicrobials is consistent with a combination of protein synthesis and gyrase A/topoisomerase IV inhibition, with a structure-dependent degree of the contribution from each inhibitory mechanism.