N-(2-butyl-3-{4-[3-(butylamino)propoxy]benzoyl}-1-benzofuran-5-yl)methanesulfonamide hydrochloride

• ChemBase ID: 166163
• Molecular Formular: C27H37ClN2O5S
• Molecular Mass: 537.11108
• Monoisotopic Mass: 536.21117097
• SMILES: c1c(cc2c(c1)oc(c2C(=O)c1ccc(cc1)OCCCNCCCC)CCCC)NS(=O)(=O)C.Cl
• Canonical SMILES: CCCCc1oc2c(c1C(=O)c1ccc(cc1)OCCCNCCCC)cc(cc2)NS(=O)(=O)C.Cl
• InChI: InChI=1S/C27H36N2O5S.ClH/c1-4-6-9-25-26(23-19-21(29-35(3,31)32)12-15-24(23)34-25)27(30)20-10-13-22(14-11-20)33-18-8-17-28-16-7-5-2;/h10-15,19,28-29H,4-9,16-18H2,1-3H3;1H
• InChIKey: ZDXBTJLIQYUYSZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-butyl-3-{4-[3-(butylamino)propoxy]benzoyl}-1-benzofuran-5-yl)methanesulfonamide hydrochloride
• IUPAC Traditional name: N-(2-butyl-3-{4-[3-(butylamino)propoxy]benzoyl}-1-benzofuran-5-yl)methanesulfonamide hydrochloride
• Synonyms: N-[2-Butyl-3-[4-[3-(butylamino)propoxy]benzoyl]-5-benzofuranyl]-methanesulfonamide Hydrochloride; SR 35021; Dronedarone Impurity D; Desbutyl Dronedarone Hydrochloride

Database IDs

• CAS Number: 197431-02-0
• PubChem SID: 162260296
• PubChem CID: 71315590

CALCULATED PROPERTIES

• Acid pKa: 9.178297
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.2209358
• LogD (pH = 7.4): 1.9480476
• Log P: 3.5616274
• Molar Refractivity: 138.9601 cm^3
• Polarizability: 55.882595 Å^3
• Polar Surface Area: 97.64 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Tan Solid
• Melting Point: 136-138°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D288875

A metabolite of Dronedarone (D679445). Dronedarone impurity D.

REFERENCES

• Bolderman, R.W. et al.: J Chrom. B:Anal. Tech. Biomed. Life Sci., 887, 1727 (2009)
• Singh, B., et al.: J. Cardiovas. Pharmacol., 52, 300 (2009)
• Hoy, S., et al.: Drugs, 69, 1647 (2009)