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

• ChemBase ID: 122528
• Molecular Formular: C27H36N6O11S
• Molecular Mass: 652.67334
• Monoisotopic Mass: 652.216277
• SMILES: c12c(nc([nH]c1=O)c1cc(S(=O)(=O)N3CCN(CC3)C)ccc1OCC)c(n[nH]2)CCC.C(CC(=O)O)(CC(=O)O)(C(=O)O)O
• Canonical SMILES: OC(=O)CC(C(=O)O)(CC(=O)O)O.CCCc1n[nH]c2c1nc([nH]c2=O)c1cc(ccc1OCC)S(=O)(=O)N1CCN(CC1)C
• InChI: InChI=1S/C21H28N6O4S.C6H8O7/c1-4-6-16-18-19(25-24-16)21(28)23-20(22-18)15-13-14(7-8-17(15)31-5-2)32(29,30)27-11-9-26(3)10-12-27;7-3(8)1-6(13,5(11)12)2-4(9)10/h7-8,13H,4-6,9-12H2,1-3H3,(H,24,25)(H,22,23,28);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
• InChIKey: OWEGBXLLNJUJOQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxypropane-1,2,3-tricarboxylic acid; 5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one
• IUPAC Traditional name: 5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-3-propyl-1H,6H-pyrazolo[4,3-d]pyrimidin-7-one; citro; 2-hydroxypropane-1,2,3-tricarboxylic acid; 5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one
• Synonyms: 5-(2-ethoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one 2-hydroxypropane-1,2,3-tricarboxylate; Viagra; Revatio; Sildenafil Citrate

Database IDs

• CAS Number: 171599-83-0
• PubChem SID: 162216881
• PubChem CID: 51052077

CALCULATED PROPERTIES

• Acid pKa: 9.068209
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.61738425
• LogD (pH = 7.4): 1.2022017
• Log P: 1.2279139
• Molar Refractivity: 124.6579 cm^3
• Polarizability: 46.537983 Å^3
• Polar Surface Area: 119.99 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Selective inhibitor of cyclic GMP specific phosphodiesterase (Type V); Vasodilator

Product Information

• Salt Data: Citrate
• Application(s): Used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH)

REFERENCES

• Eur. Pat., 1992, Pfizer, 463 756; CA, 116, 255626q, (synth, pharmacol)
• Terrett, N.K. et al., Bioorg. Med. Chem. Lett., 1996, 6, 1819-1824, (sildenafil citrate)
• Boolell, M. et al., Br. J. Urol., 1996, 78, 257-261, (pharmacol)
• Martel, A.M. et al., Drugs of the Future, 1997, 22, 138-143, (synth, pharmacol)
• Cooper, J.D.H. et al., J. Chromatogr., B: Biomed. Appl., 1997, 701, 87-95, (hplc)
• Morales, A. et al., Int. J. Impot. Res., 1998, 10, 69-74, (use)
• Ballard, S.A. et al., J. Urol. (Baltimore), 1998, 159, 2164-2171; 160, 242-246, (pharmacol)
• Chuang, A.T. et al., J. Urol. (Baltimore), 1998, 160, 257-261, (pharmacol)
• Palmer, E., Chem. Br., 1999, 24-26, (rev)
• Cheitlin, M.D. et al., Circulation, 1999, 99, 168-177
• Langtry, H.D. et al., Drugs, 1999, 57, 967-989
• Noss, M.B. et al., Drugs of Today (Barcelona), 1999, 35, 211-217
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1629
• Dale, D.J. et al., Org. Process Res. Dev., 2000, 4, 17-22, (synth)