N-{[(5S)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}(2H3)acetamide

• ChemBase ID: 172307
• Molecular Formular: C16H20FN3O4
• Molecular Mass: 337.3461032
• Monoisotopic Mass: 337.14378436
• SMILES: O1CCN(CC1)c1c(cc(cc1)N1C[C@@H](OC1=O)CNC(=O)C)F
• Canonical SMILES: CC(=O)NC[C@@H]1OC(=O)N(C1)c1ccc(c(c1)F)N1CCOCC1
• InChI: InChI=1S/C16H20FN3O4/c1-11(21)18-9-13-10-20(16(22)24-13)12-2-3-15(14(17)8-12)19-4-6-23-7-5-19/h2-3,8,13H,4-7,9-10H2,1H3,(H,18,21)/t13-/m0/s1
• InChIKey: TYZROVQLWOKYKF-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{[(5S)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}(^2H₃)acetamide
• IUPAC Traditional name: N-{[(5S)-3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl}(^2H₃)acetamide
• Synonyms: N-[[(5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide-d3; Linospan-d3; Linox-d3; PNU 100766-d3; U 100766-d3; Zyvox-d3; Zyvoxid-d3; Linezolid-d3

Database IDs

• CAS Number: 1127120-38-0
• PubChem SID: 164228217
• PubChem CID: 25217322

CALCULATED PROPERTIES

• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 14.453722
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.6366634
• LogD (pH = 7.4): 0.6366636
• Log P: 0.6366637
• Molar Refractivity: 84.4748 cm^3
• Polarizability: 32.025 Å^3
• Polar Surface Area: 71.11 Å^2

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 174-176°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - L466502

Labelled Linezolid. Prototype of the oxazolidinone antimicrobials; inhibits bacterial mRNA translation.

REFERENCES

• Brickner, S.J., et al.: J. Med. Chem., 39, 673 (1996)
• Ford, C.W., et al.: Antimicrob. Agents Chemother., 40, 1508 (1996)
• Rybak, M.J., et al.: Pharmacotherapy, 18, 456 (1996)
• Stevens, D.L., et al.: Clin. Infect. Dis., 34, 1481 (1996)