6-({2-[(2-hydroxyethyl)[3-(4-nitrophenyl)propyl]amino]ethyl}amino)-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride

• ChemBase ID: 175146
• Molecular Formular: C19H28ClN5O5
• Molecular Mass: 441.90912
• Monoisotopic Mass: 441.1778967
• SMILES: c1(CCCN(CCNc2cc(=O)n(c(=O)n2C)C)CCO)ccc(cc1)[N+](=O)[O-].Cl
• Canonical SMILES: OCCN(CCNc1cc(=O)n(c(=O)n1C)C)CCCc1ccc(cc1)[N+](=O)[O-].Cl
• InChI: InChI=1S/C19H27N5O5.ClH/c1-21-17(14-18(26)22(2)19(21)27)20-9-11-23(12-13-25)10-3-4-15-5-7-16(8-6-15)24(28)29;/h5-8,14,20,25H,3-4,9-13H2,1-2H3;1H
• InChIKey: YPVGGQKNWAKOPX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-({2-[(2-hydroxyethyl)[3-(4-nitrophenyl)propyl]amino]ethyl}amino)-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride
• IUPAC Traditional name: nifekalant hydrochloride
• Synonyms: 6-[[2-[(2-Hydroxyethyl)[3-(4-nitrophenyl)propyl]amino]ethyl]amino]-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione Hydrochloride; MS 551; Shinbit; Nifekalant Hydrochloride

Database IDs

• CAS Number: 130656-51-8
• PubChem SID: 164231056
• PubChem CID: 122188

CALCULATED PROPERTIES

• Acid pKa: 15.593175
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.7862936
• LogD (pH = 7.4): -0.085520335
• Log P: 1.2496718
• Molar Refractivity: 119.078 cm^3
• Polarizability: 40.85883 Å^3
• Polar Surface Area: 121.94 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO (Sparingly); Methanol (Sparingly); Water
• Apperance: Yellow Solid
• Melting Point: 173-177°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - N457100

Nifekalant Hydrochloride is a class III antiarrhythmic agent. Nifekalant Hydrochloride is used in the treatment of patients with extensive anterior infarction and severe ventricular dysfunction.

REFERENCES

• Takenaka, K. Jap. Circ. J., 65, 60 (2001)
• Igawa, M. et al.: J. Cardio. Pharmacol., 40, 735 (2001)
• Washizuka, T. et al.: Circ. J., 69, 1508 (2001)