5-[2-ethoxy-5-(piperazine-1-sulfonyl)phenyl]-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one

• ChemBase ID: 166546
• Molecular Formular: C21H28N6O4S
• Molecular Mass: 460.54982
• Monoisotopic Mass: 460.18927441
• SMILES: C1NCCN(C1)S(=O)(=O)c1ccc(c(c1)c1nc2c(c(=O)[nH]1)n(nc2CCC)C)OCC
• Canonical SMILES: CCCc1nn(c2c1nc([nH]c2=O)c1cc(ccc1OCC)S(=O)(=O)N1CCNCC1)C
• InChI: InChI=1S/C21H28N6O4S/c1-4-6-16-18-19(26(3)25-16)21(28)24-20(23-18)15-13-14(7-8-17(15)31-5-2)32(29,30)27-11-9-22-10-12-27/h7-8,13,22H,4-6,9-12H2,1-3H3,(H,23,24,28)
• InChIKey: UZTKBZXHEOVDRL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[2-ethoxy-5-(piperazine-1-sulfonyl)phenyl]-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one
• IUPAC Traditional name: 5-[2-ethoxy-5-(piperazine-1-sulfonyl)phenyl]-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one
• Synonyms: 5-[2-Ethoxy-5-(1-piperazinylsulfonyl)phenyl]-1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one; Desmethylsildenafil; UK 103320; N-Desmethyl Sildenafil

Database IDs

• CAS Number: 139755-82-1
• PubChem SID: 162260679
• PubChem CID: 6426858

CALCULATED PROPERTIES

• Acid pKa: 8.988146
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.6927012
• LogD (pH = 7.4): 0.76055264
• Log P: 0.8720575
• Molar Refractivity: 134.5792 cm^3
• Polarizability: 46.460396 Å^3
• Polar Surface Area: 117.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: White Solid
• Melting Point: 158-160°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D292200

A metabolite of Sildenafil, an orally active selective type 5 cGMP phosphodiesterase inhibitor.

REFERENCES

• Walker, D; Xenobiotica, 29, 297 (1999)
• Shim, H., et al.: J. Pharm. Biomed. Anal., 30, 527 (1999)
• Kim, J., et al.: J. Pharm. Biomed. Anal., 32, 317 (1999)
• Pelander, A., et al.: J. Anal. Toxicol., 27, 226 (1999)