3,5-dichloro-4-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzamido]pyridin-1-ium-1-olate

• ChemBase ID: 177589
• Molecular Formular: C17H14Cl2F2N2O4
• Molecular Mass: 419.2068664
• Monoisotopic Mass: 418.02986874
• SMILES: c1(c(cc(cc1)C(=O)Nc1c(c[n+](cc1Cl)[O-])Cl)OCC1CC1)OC(F)F
• Canonical SMILES: FC(Oc1ccc(cc1OCC1CC1)C(=O)Nc1c(Cl)c[n+](cc1Cl)[O-])F
• InChI: InChI=1S/C17H14Cl2F2N2O4/c18-11-6-23(25)7-12(19)15(11)22-16(24)10-3-4-13(27-17(20)21)14(5-10)26-8-9-1-2-9/h3-7,9,17H,1-2,8H2,(H,22,24)
• InChIKey: PCGSQNPMMSALEJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-dichloro-4-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzamido]pyridin-1-ium-1-olate
• IUPAC Traditional name: 3,5-dichloro-4-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzamido]pyridin-1-ium-1-olate
• Synonyms: 3-(Cyclopropylmethoxy)-N-(3,5-dichloro-1-oxido-4-pyridinyl)-4-(difluoromethoxy)benzamide; N-(3,5-Dichloro-1-oxopyridin-4-yl)-4-difluoromethoxy-3-cyclopropyl-methoxybenzamide; Roflumilast N-Oxide

Database IDs

• CAS Number: 292135-78-5
• PubChem SID: 164233499
• PubChem CID: 9940999

CALCULATED PROPERTIES

• Acid pKa: 7.26144
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.1802988
• LogD (pH = 7.4): 2.8403647
• Log P: 3.1873837
• Molar Refractivity: 97.611 cm^3
• Polarizability: 35.92381 Å^3
• Polar Surface Area: 73.02 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off White Solid
• Melting Point: 178-180°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R639710

Roflumilast-N-oxide is the active metabolite of Roflumilast (R639700).

REFERENCES

• Chiba, M., et al.: Drug Metab. Dispos., 25, 1022 (1997)
• Jarvis, B., et al.: Drugs, 59, 891 (1997)