4-(4-ethoxy-3-{1-methyl-7-oxo-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-5-yl}benzenesulfonyl)-1-methylpiperazin-1-ium-1-olate

• ChemBase ID: 177762
• Molecular Formular: C22H30N6O5S
• Molecular Mass: 490.5758
• Monoisotopic Mass: 490.19983909
• SMILES: C1[N+](CCN(C1)S(=O)(=O)c1ccc(c(c1)c1nc2c(c(=O)[nH]1)n(nc2CCC)C)OCC)(C)[O-]
• Canonical SMILES: CCCc1nn(c2c1nc([nH]c2=O)c1cc(ccc1OCC)S(=O)(=O)N1CC[N+](CC1)([O-])C)C
• InChI: InChI=1S/C22H30N6O5S/c1-5-7-17-19-20(26(3)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)33-6-2)34(31,32)27-10-12-28(4,30)13-11-27/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)
• InChIKey: JQGFLCMKCZPSEC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(4-ethoxy-3-{1-methyl-7-oxo-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-5-yl}benzenesulfonyl)-1-methylpiperazin-1-ium-1-olate
• IUPAC Traditional name: 4-(4-ethoxy-3-{1-methyl-7-oxo-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-5-yl}benzenesulfonyl)-1-methylpiperazin-1-ium-1-olate
• Synonyms: 5-[2-Ethoxy-5-[(4-methyl-4-oxido-1-piperazinyl)sulfonyl]phenyl]-1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one; Sildenafil N-Oxide

Database IDs

• CAS Number: 1094598-75-0
• PubChem SID: 164233672
• PubChem CID: 25144335

CALCULATED PROPERTIES

• Acid pKa: 8.981586
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.22698589
• LogD (pH = 7.4): 0.21727462
• Log P: 0.22721478
• Molar Refractivity: 141.9188 cm^3
• Polarizability: 48.486153 Å^3
• Polar Surface Area: 132.77 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S435035

Sildenafil N-Oxide is an impurity of Sildenafil citrate (S435000), as prodrug.

REFERENCES

• Bickel, M., et al.: Pharmacol. Rev., 21, 325 (1969)