sodium 5-chloro-3-[ethyl(2H5)phenylcarbamoyl]-1-methyl-2-oxo-1,2-dihydroquinolin-4-olate

• ChemBase ID: 172225
• Molecular Formular: C19H16ClN2NaO3
• Molecular Mass: 378.78471
• Monoisotopic Mass: 378.07471434
• SMILES: c1cc(c2c(c1)n(c(=O)c(c2[O-])C(=O)N(c1ccccc1)CC)C)Cl.[Na+]
• Canonical SMILES: CCN(C(=O)c1c([O-])c2c(Cl)cccc2n(c1=O)C)c1ccccc1.[Na+]
• InChI: InChI=1S/C19H17ClN2O3.Na/c1-3-22(12-8-5-4-6-9-12)19(25)16-17(23)15-13(20)10-7-11-14(15)21(2)18(16)24;/h4-11,23H,3H2,1-2H3;/q;+1/p-1
• InChIKey: JWHPPWBIIQMBQC-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 5-chloro-3-[ethyl(^2H₅)phenylcarbamoyl]-1-methyl-2-oxo-1,2-dihydroquinolin-4-olate
• IUPAC Traditional name: sodium 5-chloro-3-[ethyl(^2H₅)phenylcarbamoyl]-1-methyl-2-oxoquinolin-4-olate
• Synonyms: 5-Chloro-N-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-N-(phenyl-d5)-3-quinolinecarboxamide Sodium Salt; ABR 215062-d5 Sodium; N-Ethyl-N-(phenyl-d5)-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide Sodium Salt; TV 5600-d5; Laquinimod-d5 Sodium Salt

Database IDs

• CAS Number: 1354744-14-1
• PubChem SID: 164228135
• PubChem CID: 71749749

CALCULATED PROPERTIES

• Acid pKa: 5.020428
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.952158
• LogD (pH = 7.4): 0.3046486
• Log P: 2.5541253
• Molar Refractivity: 107.8586 cm^3
• Polarizability: 36.54554 Å^3
• Polar Surface Area: 63.68 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L175902

Labelled Laquinimod (L175900). Laquinimod is an oral drug used for treatment of lupus arthritis.

REFERENCES

• Wiseman, E., et al.: J. Med. Chem., 16, 131 (1973)
• Noseworthy, J., et al.: Neurology, 54, 1726 (1973)
• Jonsson, S., et al.: J. Med. Chem., 47, 2075 (1973)
• Tuvesson, H., et al.: Drug Metab. Dispos., 33, 866 (1973)