Sutezolid

Base Information

• Chemical Name: Sutezolid
• CAS No.: 168828-58-8
• Molecular Formula: C16H20 F N3 O3 S
• Molecular Weight: 353.418
• European Community (EC) Number: 809-216-7
• NSC Number: 742407
• UNII: 3A71182L8P
• DSSTox Substance ID: DTXSID20168611
• Nikkaji Number: J3.052.265F,J727.962K
• Wikipedia: Sutezolid
• Wikidata: Q15427841
• NCI Thesaurus Code: C152482
• Pharos Ligand ID: VVUN3HRPPMRP
• Metabolomics Workbench ID: 152986
• ChEMBL ID: CHEMBL288149
• Mol file: 168828-58-8.mol

Synonyms:PNU-100480;sutezolid;U-480 compound

Chemical Property of Sutezolid

Chemical Property:

• Vapor Pressure: 8.97E-15mmHg at 25°C
• Melting Point: 186-187°C
• Boiling Point: 609°C at 760 mmHg
• PKA: 15.53±0.46(Predicted)
• Flash Point: 322.1°C
• PSA: 87.18000
• Density: 1.321g/cm³
• LogP: 2.36110
• Storage Temp.: room temp
• Solubility.: DMSO: soluble20mg/mL, clear
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 353.12094084
• Heavy Atom Count: 24
• Complexity: 476

Purity/Quality:

98%,99%, ^*data from raw suppliers

Sutezolid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NCC1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCSCC3)F
• Isomeric SMILES: CC(=O)NC[C@H]1CN(C(=O)O1)C2=CC(=C(C=C2)N3CCSCC3)F
• Recent ClinicalTrials: PanACEA Sutezolid Dose-finding and Combination Evaluation
• Description: PNU 100480 is an oxazolidinone antibiotic that is active against multidrug resistant tuberculosis. It inhibits the growth of M. tuberculosis replicating and nonreplicating strains (MIC = ~400 ng/ml for both) and of clinical isolates that are susceptible or resistant to a combination of isoniazid , rifampin (rifampicin; ), ethambutol , and streptomycin (; MICs = ≤0.0625-0.5 mg/L). It also inhibits the growth of P. insidiosum and P. aphanidermatum clinical isolates (MICs = 4-64 μg/ml). PNU 100480 (100 mg/kg per day) decreases the number of colony forming units (CFU) in the lung in a mouse model of systemic nonreplicating M. tuberculosis infection.
• Uses: Sutezolid is an oxazolidinone antibacterial agent analog. Sutezolid is a promising antimycobacterial agent (tuberculostatic).

Technology Process of Sutezolid

There total 13 articles about Sutezolid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

(S)-5-(aminomethyl)-3-(3-fluoro-4-thiomorpholinophenyl)oxazolidin-2-one hydrochloride + acetic anhydride (108-24-7) → sutezolid (168828-58-8)

Guidance literature:

With sodium hydroxide; In methanol; dichloromethane; water; ethyl acetate; at 20 ℃; for 1.25h;

Reference yield: 91.0%

→ sutezolid (168828-58-8)

Guidance literature:

Reference yield:

[[3-[3-fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]azide → sutezolid (168828-58-8)

Guidance literature:

With pyridine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; acetonitrile;

upstream raw materials:

acetic anhydride

(5S)-5-(aminomethyl)-3-(3-fluoro-4-thiomorpholin-4-ylphenyl)-1,3-oxazolidin-2-one

3,4-difluoronitrobenzene

(3-fluoro-4-thiomorpholin-4-ylphenyl)amine

Downstream raw materials:

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

Refernces

• 1、 -. "Combination Therapy for Tuberculosis". . . Retrieved 2011/08/08.
• 2、 Barbachyn, Michael R.,Hutchinson, Douglas K.,Brickner, Steven J.,Cynamon, Michael H.,Kilburn, James O.,et al.. "Identification of a novel oxazolidinone (U-100480) with potent antimycobacterial activity.". . p. 680 - 685. Retrieved 2007/10/03.