168828-58-8

Basic information

• Product Name: PNU 100480
• Synonyms: PNU 100480;(S)-N-[[3-[3-Fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide;Sutezolid;(S)-N-((3-(3-fluoro-4-thiomorpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide;(S)-N-((3-(3-fluoro-4-thiomorpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide(WXC06631);PF-02341272
• CAS NO: 168828-58-8
• Molecular Formula: C₁₆H₂₀FN₃O₃S
• Molecular Weight: 353.4117032
• Mol File: 168828-58-8.mol

Chemical Properties

• Boiling Point: 609°C at 760 mmHg
• Flash Point: 322.1°C
• Appearance: white to beige/
• Density: 1.321g/cm³
• Vapor Pressure: 8.97E-15mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: room temp
• Solubility: DMSO: soluble20mg/mL, clear
• PKA: 15.53±0.46(Predicted)
• CAS DataBase Reference: PNU 100480(CAS DataBase Reference)
• NIST Chemistry Reference: PNU 100480(168828-58-8)
• EPA Substance Registry System: PNU 100480(168828-58-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 45
• Hazardous Substances Data: 168828-58-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
PNU 100480 is used as an antimycobacterial agent for the treatment of multidrug-resistant tuberculosis. It is effective against both replicating and nonreplicating strains of M. tuberculosis, as well as clinical isolates resistant to a combination of isoniazid, rifampin, ethambutol, and streptomycin.
Used in Research and Development:
PNU 100480 is used as a research compound for studying the mechanisms of action against tuberculosis and other related mycobacterial infections. Its activity against P. insidiosum and P. aphanidermatum clinical isolates also makes it a valuable tool for investigating potential treatments for these infections.
Used in Drug Resistance Studies:
PNU 100480 is used to investigate the development of drug resistance in M. tuberculosis and other mycobacterial species. Understanding the resistance patterns and mechanisms can help in the development of new strategies to combat drug-resistant infections.

Biochem/physiol Actions

Sutezolid (PNU 100480) is an oxazolidinone antimicrobial. Sutezolid inhibits protein synthesis by inhibiting bacterial mRNA translation. Sutezolid is being investigated for the treatment of multiple drug–resistant and extensively drug-resistant tuberculosis. The compound is a less toxic and more potent derivative of linezolid.

InChI:InChI=1/C16H20FN3O3S/c1-11(21)18-9-13-10-20(16(22)23-13)12-2-3-15(14(17)8-12)19-4-6-24-7-5-19/h2-3,8,13H,4-7,9-10H2,1H3,(H,18,21)/t13-/m0/s1

Upstream product

• 108-24-7 acetic anhydride 
• 168828-71-5 [3-fluoro-4-(4-thiomorpholinyl)phenyl]carbamic acid, phenylmethyl ester 
• 168828-72-6 (R)-<3-<3-fluoro-4-(4-thiomorpholinyl)phenyl>-2-oxo-5-oxazolidinyl>methanol 
• 168828-70-4 (4-(2-fluoro-4-nitrophenyl)thiomorpholine) 
• 237432-11-0 (3-fluoro-4-thiomorpholin-4-ylphenyl)amine 
• 369-34-6 3,4-difluoronitrobenzene 
• 216869-36-2 (5S)-5-(aminomethyl)-3-(3-fluoro-4-thiomorpholin-4-ylphenyl)-1,3-oxazolidin-2-one 
• 168828-73-7 Toluene-4-sulfonic acid (R)-3-(3-fluoro-4-thiomorpholin-4-yl-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester 
• 174678-78-5 (R)-<3-<3-fluoro-4-(4-thiomorpholinyl)phenyl>-2-oxo-5-oxazolidinyl>methyl methanesulfonate 
• 168828-74-8 (R)-<3-<3-fluoro-4-(4-thiomorpholinyl)phenyl>-2-oxo-5-oxazolidinyl>methyl azide 

Downstream Products

• 168828-60-2 N-[[(5S)-3-[3-fluoro-4-(1-oxido-4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 

Relevant articles and documents

Combination Therapy for Tuberculosis

The present invention relates to methods of treating tuberculosis, including multi-drug resistant varieties and latent tuberculosis. More particularly, the present invention relates to a method of treating tuberculosis in a mammal comprising administering

Combination Therapy for Tuberculosis

The present invention relates to methods of treating tuberculosis, including multi-drug resistant varieties and latent tuberculosis. More particularly, the present invention relates to a method of treating tuberculosis in a mammal comprising administering to said mammal in need thereof an effective amount of a compound of formula (I), (S)—N-[[3-[3-fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide, or a pharmaceutically acceptable salt thereof in combination with at least two agents useful in the treatment of tuberculosis. The present invention also relates to a pharmaceutical composition comprising a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof, (ii) a therapeutically effective amount of at least one agent useful in the treatment of tuberculosis and (iii) one or more pharmaceutically acceptable carriers or vehicles.

Substituted oxazine and thiazine oxazolidinone antimicrobials

A compound of structural Formula I: STR1 or pharmaceutically acceptable salts thereof wherein: X is O, S, SO, SO2, SNR10 or S(O)NR10 ; R is (a) hydrogen, (b) C1 -C8 alkyl optionally substituted with one or more of the following: F, Cl, hydroxy, C1 -C8 alkoxy, C1 -C8 acyloxy or --O--CH2 --Ph, (c) C3 -C6 cycloalkyl, (d) amino, (e) C1 -C8 alkylamino, (f) C1 -C8 dialkylamino or (g) C1 -C8 alkoxy; R1 is H, except when X is O then R1 can be H, CH3, CN, CO2 H, CO2 R or (CH2)m R11 (m is 1 or 2); R2 is independently H, F or Cl; R3 is H except when X is O and R1 is CH3 then R3 can be H or CH3 ; R10 is independently H, C1 -C4 alkyl (optionally substituted with chloro, fluoro, hydroxy, C1 -C8 alkoxy, amino, C1 -C8 alkylamino, or C1 -C8 dialkylamino) or p-toluenesulfonyl; R11 is hydrogen, OH, OR, OCOR, NH2, NHCOR or N(R10)2 ; and n is 0, 1 or 2. The oxazine and thiazine oxazolidinone derivatives are useful antimicrobial agents, effective against a number of human and veterinary pathogens, including gram-positive aerobic bacteria such as multiply-resistant staphylococci, streptococci and enterococci as well as anaerobic organisms such as Bacteroides spp. and Clostridia spp. species, and acid-fast organisms such as Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium spp.

Identification of a novel oxazolidinone (U-100480) with potent antimycobacterial activity.

During the course of our investigations in the oxazolidinone antibacterial agent area, we have identified a subclass with especially potent in vitro activity against mycobacteria. The salient structural feature of these oxazolidinone analogues, 6 (U-10048