5-(2-ethoxy-5-{[4-(2H3)methylpiperazin-1-yl]sulfonyl}phenyl)-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one

• ChemBase ID: 177760
• Molecular Formular: C22H30N6O4S
• Molecular Mass: 474.5764
• Monoisotopic Mass: 474.20492447
• SMILES: C1N(CCN(C1)S(=O)(=O)c1ccc(c(c1)c1nc2c(c(=O)[nH]1)n(nc2CCC)C)OCC)C
• Canonical SMILES: CCCc1nn(c2c1nc([nH]c2=O)c1cc(ccc1OCC)S(=O)(=O)N1CCN(CC1)C)C
• InChI: InChI=1S/C22H30N6O4S/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)
• InChIKey: BNRNXUUZRGQAQC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(2-ethoxy-5-{[4-(^2H₃)methylpiperazin-1-yl]sulfonyl}phenyl)-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one
• IUPAC Traditional name: 5-{2-ethoxy-5-[4-(^2H₃)methylpiperazin-1-ylsulfonyl]phenyl}-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one
• Synonyms: 1-[[3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methylpiperazine-d3; 5-[2-Ethoxy-5-[[4-(methyl-d3)-1-piperazinyl]sulfonyl]phenyl]-1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one; Sildenafil-d3

Database IDs

• CAS Number: 1126745-90-1
• PubChem SID: 164233670
• PubChem CID: 25217315

CALCULATED PROPERTIES

• Acid pKa: 8.982032
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.74111515
• LogD (pH = 7.4): 1.3251485
• Log P: 1.3515899
• Molar Refractivity: 139.8739 cm^3
• Polarizability: 48.292347 Å^3
• Polar Surface Area: 109.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 187-189°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Store in Freezer

DETAILS

Toronto Research Chemicals - S435002

Labelled Sildenafil, an orally active selective type 5 cGMP phosphodiesterase inhibitor.

REFERENCES

• Terrett, N.K., et al.: Bioorg. Med. Chem. Lett., 6, 1819 (1996)
• Goldstein, I., et al.: N. Engl. J. Med., 338, 1397 (1996)