(5S)-5-[4-methoxy-3-(2H7)propoxyphenyl]-5-methyl-1,3-oxazolidin-2-one

• ChemBase ID: 172694
• Molecular Formular: C14H19NO4
• Molecular Mass: 265.30496
• Monoisotopic Mass: 265.13140809
• SMILES: c1(c(ccc(c1)[C@@]1(OC(=O)NC1)C)OC)OCCC
• Canonical SMILES: CCCOc1cc(ccc1OC)[C@@]1(C)CNC(=O)O1
• InChI: InChI=1S/C14H19NO4/c1-4-7-18-12-8-10(5-6-11(12)17-3)14(2)9-15-13(16)19-14/h5-6,8H,4,7,9H2,1-3H3,(H,15,16)/t14-/m1/s1
• InChIKey: PCCPERGCFKIYIS-CQSZACIVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-5-[4-methoxy-3-(^2H₇)propoxyphenyl]-5-methyl-1,3-oxazolidin-2-one
• IUPAC Traditional name: (5S)-5-[4-methoxy-3-(^2H₇)propoxyphenyl]-5-methyl-1,3-oxazolidin-2-one
• Synonyms: (5S)-5-[4-Methoxy-3-(propoxy-d7)phenyl]-5-methyl-2-oxazolidinone; (S)-5-[4-Methoxy-3-(propoxy-d7)phenyl]-5-methyl-2-oxazolidinone; (S)-Mesopram-d7

Database IDs

• PubChem SID: 164228604
• PubChem CID: 71749972

CALCULATED PROPERTIES

• Acid pKa: 12.725929
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.2699585
• LogD (pH = 7.4): 2.2699568
• Log P: 2.2699585
• Molar Refractivity: 70.1372 cm^3
• Polarizability: 27.604578 Å^3
• Polar Surface Area: 56.79 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M225677

The labelled S-isomer of Mesopram (M225670). Mesopram is an orally active phosphodiesterase (PDE) 4 inhibitor. Mesopram decreases the synthesis of tumor necrosis factor-α (TNF-α) and interferon-γ (IFN-γ). Mesopram is used in compositions for the treatment

REFERENCES

• Axelsson, L., et al.: Aliment Pharmacol. Ther., 12, 925 (1998)
• Doherty, A., et al.: J. Immunol., 164, 1117 (1998)
• Francischi, J., et al.: Eur. J. Pharmacol . 399, 243 (1998)
• Siegmund, B., et al.: J. Pharmacol. Exp. Ther., 296, 99 (1998)