165800-04-4

Basic information

• Product Name: eperezolid
• Synonyms: eperezolid;N-[[(5S)-3-[3-fluoro-4-[4-(2-hydroxyacetyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]-Acetamide;PNU 100592;(S)-N-[[3-[3-Fluoro-4-[4-(hydroxyacetyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide;U 100592;Eperezolid-d3
• CAS NO: 165800-04-4
• Molecular Formula: C₁₈H₂₃FN₄O₅
• Molecular Weight: 394.401
• Mol File: 165800-04-4.mol

Chemical Properties

• Melting Point: 174-176℃
• Boiling Point: 701.2°C at 760 mmHg
• Flash Point: 377.9°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 1.22E-20mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: 2-8°C
• Solubility: insoluble in EtOH; insoluble in H2O; ≥14.05 mg/mL in DMSO
• PKA: 13.84±0.10(Predicted)
• CAS DataBase Reference: eperezolid(CAS DataBase Reference)
• NIST Chemistry Reference: eperezolid(165800-04-4)
• EPA Substance Registry System: eperezolid(165800-04-4)

Safety Data

• Hazardous Substances Data: 165800-04-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 165800-04-4 differently. You can refer to the following data:
1. Antibacterial.
2. Eperezolid is an antimicrobial.

Biological Activity

mic50: 0.5, 1.0, 2.0, 1.0, 16.0 and 2.0 mg/l for pcptostreptococcus, propionibacterium acnes, ciostridium pefringens, clostridium dijiicile, bactrroidesjagilis, and fusobacterium, respectivleyanaerobic bacteria are a common cause of serious infections. anaerobic species which predominate in clinical infections include the bacteroides fragilis group, clostridium spp. and peptostreptococcus spp. the oxazolidinones are a novel class of synthetic antimicrobials inhibiting the initiation of protein synthesis. two compounds of this class, eperezolid and linezolid have been shown to inhibit enterococcus faecalis and enterococcus faecium.

in vitro

ninety per cent of all tested propionibacterium acnes (30 strains), peptostreptococccuj spp. (50 strains), c. perjringens (50 strains) and c. dficile (50 strains) were inhibited by <2 mg/l eperezolid. linezolid showed higher activity (mic90 4.0 mg/l) against b. jragilis (100 strains) compared to eperezolid (mic90 16 mg/l) [1].

in vivo

the in vivo effectiveness of eperezolid and linezolid against one strain each of enterococcus faecalis and vancomycin-resistant enterococcus faecium was examined in a rat intraabdominal abscess model. eperezolid was ineffective at doses of 25 mg/kg of body weight twice daily for the reductions in abscess bacterial density for e. faecalis. against e. faecium infections, intravenous eperezolid was effective, reducing densities approximately 2 log10 cfu/g [2].

references

[1] edlund c, oh h, nord ce. in vitro activity of linezolid and eperezolid against anaerobic bacteria. clin microbiol infect. 1999;5(1):51-53.[2] schülin t, thauvin-eliopoulos c, moellering rc jr, eliopoulos gm. activities of the oxazolidinones linezolid and eperezolid in experimental intra-abdominal abscess due to enterococcus faecalis or vancomycin-resistant enterococcus faecium. antimicrob agents chemother. 1999;43(12):2873-6.[3] schaadt rd, batts dh, daley-yates pt, pawsey sd, stalker dj, zurenko ge. serum inhibitory titers and serum bactericidal titers for human subjects receiving multiple doses of the antibacterial oxazolidinones eperezolid and linezolid. diagn microbiol infect dis. 1997;28(4):201-4.

InChI:InChI=1/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

Upstream product

• 19810-31-2 Benzyloxyacetyl chloride 
• 174649-06-0 (S)-N-[[3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
• 174649-05-9 (S)-N-[[3-[3-fluoro-4-[4-carbobenzoxypiperazin-1-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]phthalimide 
• 903594-02-5 4-[2-Fluoro-4-((R)-5-methanesulfonyloxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperazine-1-carboxylic acid benzyl ester 
• 174649-03-7 N-carbobenzoxy-3-fluoro-4-(N-carbobenzoxypiperazin-1-yl)aniline 
• 198410-25-2 (S)-N-(3-(3-fluoro-4-((N-4-carbobenzoxy)piperazin-1-yl)phenyl)-2-oxo-oxazolidin-5-yl)methylamine 
• 174649-04-8 (R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methanol 
• 183905-31-9 N-[(2S)-2-acetoxy-3-chloropropyl]acetamide 
• 183805-10-9 N-[(2S)oxiranylmethyl]acetamide 
• 239438-42-7 C₃₅H₄₂F₂N₆O₁₀ 
• 239438-46-1 C₃₂H₃₈F₂N₆O₁₀ 
• 239438-47-2 (R)-3-{3-Fluoro-4-[4-(2-hydroxy-acetyl)-piperazin-1-yl]-phenyl}-5-hydroxymethyl-oxazolidin-2-one 
• 154590-66-6 (S)-N-[[3-[3-fluoro-4-(1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 
• 507-09-5 tiolacetic acid 

Downstream Products

• 912552-58-0 4-{4-[benzyloxycarbonyl-(3-oxo-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester 
• 912552-57-9 4-{4-[benzyloxycarbonyl-(3-hydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester 
• 912552-59-1 4-{4-[Benzyloxycarbonyl-((S)-2,3-dihydroxy-propyl)-amino]-2-fluoro-phenyl}-piperazine-1-carboxylic acid benzyl ester 
• 174649-04-8 (R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methanol 
• 198410-25-2 (S)-N-(3-(3-fluoro-4-((N-4-carbobenzoxy)piperazin-1-yl)phenyl)-2-oxo-oxazolidin-5-yl)methylamine 
• 903594-02-5 4-[2-Fluoro-4-((R)-5-methanesulfonyloxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperazine-1-carboxylic acid benzyl ester 
• 239438-48-3 (R)-[N-3-[3-fluoro-4-[N-1-(4-carbobenzoxy)piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methyl azide 

Relevant articles and documents

A convenient synthesis of oxazolidinone derivatives linezolid and eperezolid from (S)-glyceraldehyde acetonide

A new convenient method for the synthesis of oxazolidinone antibacterials Linezolid and Eperezolid from readily available (S)-glyceraldehyde acetonide was developed. The key steps include reductive amination of arylamine and (S)-glyceraldehyde acetonide in the presence of NaBH4 and 4 A sieve, followed by hydrolysis and regioselective cyclization.

Short and practical enantioselective synthesis of linezolid and eperezolid via proline-catalyzed asymmetric α-aminooxylation

An efficient enantioselective synthesis of the antibacterials, linezolid (U-100766), and eperezolid (U-100592) using d-proline-catalyzed asymmetric α-aminooxylation of aldehydes as the key step is described here. This is the first report on the enantioselective synthesis of linezolid and eperezolid using asymmetric catalysis.

Treating infections by administration of oxazolidinones

Disclosed is a method of treating ear infections, soft-tissue infections, acne, or cellulitis in a mammal in need thereof comprising administration of Oxazolidinone in a pharmaceutical formulation or composition to the skin of the mammal at a site proximal to the site of the infection to deliver a pharmaceutically-effective amount of Oxazolidinone to the infection to have a concentration of the Oxazolidinone at the site of infection of about 0.5 to about 4 μg/ml, provided that the application for administration is not directly to the site of the infection.

USE OF OXAZOLIDINONE DERIVATIVES FOR TREATING ARTHRITIS

The present invention is a method of treating a person who has psoriasis or arthritis or reducing the toxicity of cancer chemotherapy which comprises administering to the patient an anti-psoriasis effective amount of an oxazolidinone, preferably (S)-N-[[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide.

TOPICAL ADMINISTRATION OF OXAZOLIDINONES FOR TRANSDERMAL DELIVERY

Disclosed is a method of treating a non-topical infection selected from the group consisting of ear infections, skin and soft tissue infections, acne, infected wounds, bacteremia, in a useful warm blooded mammal who is in need of such treatment which comprises topical administration of a pharmaceutical formulation containing a transdermally effective amount of an OXAZOLIDINONE.

Treatment of urinary tract infections with antibacterial oxazolidinones

The present invention is a method of treating a warm blooded mammal who has a urinary tract infection caused by a Gram-positive organism who is in need of such treatment, which comprises administering to the mammal in need of such treatment a urinary therapeutically effective amount of an antibacterial oxazolidinone.

A short synthesis of oxazolidinone derivatives linezolid and eperezolid: A new class of antibacterials

Oxazolidinone derivatives such as Linezolid and Eperazolid, which are a new class of antibacterials, have been synthesized from 1,2,5,6-dianhydro- 3,4-isopropylidine-D-mannitol in good yield.

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.

Bacterial resistance development has become a very serious clinical problem for many classes of antibiotics. The 3-aryl-2-oxazolidinones are a relatively new class of synthetic antibacterial agents, having a new mechanism of action which involves very early inhibition of bacterial protein synthesis. We have prepared two potent, synthetic oxazolidinones, U-100592 and U-100766, which are currently in clinical development for the treatment of serious multidrug-resistant Gram-positive bacterial infections caused by strains of staphylococci, streptococci, and enterococci. The in vitro and in vivo (po and iv) activities of U-100592 and U-100766 against representative strains are similar to those of vancomycin. U-100592 and U-100766 demonstrate potent in vitro activity against Mycobacterium tuberculosis. A novel and practical asymmetric synthesis of (5S)-(acetamidomethyl)-2-oxazolidinones has been developed and is employed for the synthesis of U-100592 and U-100766. This involves the reaction of N-lithioarylcarbamates with (R)-glycidyl butyrate, resulting in excellent yields and high enantiomeric purity of the intermediate (R)-5-(hydroxymethyl)-2-oxazolidinones.

Dynamic kinetic resolution of epichlorohydrin via enantioselective catalytic ring opening with TMSN3. Practical synthesis of aryl oxazolidinone antibacterial agents

The dynamic kinetic resolution of racemic epichlorohydrin has been achieved via enantioselective asymmetric ring opening with TMSN3 catalyzed by the (salen)Cr(III)N3 complex 1. The resulting 3-azido-1-chloro-2-trimethylsiloxypropane product was obtained in high enantiomeric purity and incorporated into the synthesis of U-100592, a representative from a class of highly-promising aryl oxazolidinone antibacterial agents.