2-[2-ethoxy-5-(piperazine-1-sulfonyl)phenyl]-5-methyl-7-propyl-3H,4H-imidazo[4,3-f][1,2,4]triazin-4-one

• ChemBase ID: 166273
• Molecular Formular: C21H28N6O4S
• Molecular Mass: 460.54982
• Monoisotopic Mass: 460.18927441
• SMILES: C1CNCCN1S(=O)(=O)c1ccc(c(c1)c1nn2c(c(=O)[nH]1)c(nc2CCC)C)OCC
• Canonical SMILES: CCCc1nc(c2n1nc([nH]c2=O)c1cc(ccc1OCC)S(=O)(=O)N1CCNCC1)C
• InChI: InChI=1S/C21H28N6O4S/c1-4-6-18-23-14(3)19-21(28)24-20(25-27(18)19)16-13-15(7-8-17(16)31-5-2)32(29,30)26-11-9-22-10-12-26/h7-8,13,22H,4-6,9-12H2,1-3H3,(H,24,25,28)
• InChIKey: OKUKNGDVADFTHE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-ethoxy-5-(piperazine-1-sulfonyl)phenyl]-5-methyl-7-propyl-3H,4H-imidazo[4,3-f][1,2,4]triazin-4-one
• IUPAC Traditional name: 2-[2-ethoxy-5-(piperazine-1-sulfonyl)phenyl]-5-methyl-7-propyl-3H-imidazo[4,3-f][1,2,4]triazin-4-one
• Synonyms: 1-[[3-(1,4-Dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-piperazine; N-Desethyl Vardenafil

Database IDs

• CAS Number: 448184-46-1
• PubChem SID: 162260406
• PubChem CID: 12018718

CALCULATED PROPERTIES

• Acid pKa: 9.002052
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.292956
• LogD (pH = 7.4): 0.16100916
• Log P: 0.27335545
• Molar Refractivity: 122.2515 cm^3
• Polarizability: 46.475643 Å^3
• Polar Surface Area: 117.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D289950

A metabolite of Vardenafil, a phosphodiesterase 5 inhibitor.

REFERENCES

• Bischoff, E., et al.: J. Urol., 165, 1316 (2001)
• Kim, N.N., et al.: Life Sci., 69, 2249 (2001)
• Kendirci, M., et al.: Expert Opin. Pharmacother., 5, 923 (2001)