5-{2-ethoxy-5-[(2,2,3,3,5,5,6,6-2H8)piperazine-1-sulfonyl]phenyl}-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidine-7-thione

• ChemBase ID: 166592
• Molecular Formular: C21H28N6O3S2
• Molecular Mass: 476.61542
• Monoisotopic Mass: 476.16643079
• SMILES: C1CNCCN1S(=O)(=O)c1ccc(c(c1)c1nc2c(c(=S)[nH]1)n(nc2CCC)C)OCC
• Canonical SMILES: CCCc1nn(c2c1nc([nH]c2=S)c1cc(ccc1OCC)S(=O)(=O)N1CCNCC1)C
• InChI: InChI=1S/C21H28N6O3S2/c1-4-6-16-18-19(26(3)25-16)21(31)24-20(23-18)15-13-14(7-8-17(15)30-5-2)32(28,29)27-11-9-22-10-12-27/h7-8,13,22H,4-6,9-12H2,1-3H3,(H,23,24,31)
• InChIKey: VMDTWBKYCKLNLA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{2-ethoxy-5-[(2,2,3,3,5,5,6,6-^2H₈)piperazine-1-sulfonyl]phenyl}-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidine-7-thione
• IUPAC Traditional name: 5-{2-ethoxy-5-[(2,2,3,3,5,5,6,6-^2H₈)piperazine-1-sulfonyl]phenyl}-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidine-7-thione
• Synonyms: 5-[2-Ethoxy-5-(1-piperazinyl-d8-sulfonyl)phenyl]-1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidine-7-thione; Desmethyl Thiosildenafil-d8

Database IDs

• CAS Number: 1215321-44-0
• PubChem SID: 162260725
• PubChem CID: 46781193

CALCULATED PROPERTIES

• Acid pKa: 11.505484
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.19676802
• LogD (pH = 7.4): 1.6597923
• Log P: 1.8584117
• Molar Refractivity: 142.5701 cm^3
• Polarizability: 49.780106 Å^3
• Polar Surface Area: 100.85 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: 193-195°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D294352

Labelled Sildenafil thiono analog, a novel pyrazolopyrimidinethiones as PDE5 inhibitor.

REFERENCES

• Walker, D., et al.: Xenobiotica, 29, 297 (1999)
• Moreland, R., et al.: Trends Endocrinol. Metab., 10, 97 (1999)