bis{2-[4-(4-ethoxy-3-{1-methyl-7-oxo-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-5-yl}benzenesulfonyl)piperazin-1-yl]ethyl} carbonate

• ChemBase ID: 172359
• Molecular Formular: C47H62N12O11S2
• Molecular Mass: 1035.19898
• Monoisotopic Mass: 1034.41024286
• SMILES: n1c([nH]c2c(c1=O)n(nc2CCC)C)c1cc(ccc1OCC)S(=O)(=O)N1CCN(CC1)CCOC(=O)OCCN1CCN(S(=O)(=O)c2ccc(c(c3[nH]c4c(nn(c4c(=O)n3)C)CCC)c2)OCC)CC1
• Canonical SMILES: CCCc1nn(c2c1[nH]c(nc2=O)c1cc(ccc1OCC)S(=O)(=O)N1CCN(CC1)CCOC(=O)OCCN1CCN(CC1)S(=O)(=O)c1ccc(c(c1)c1nc(=O)c2c([nH]1)c(CCC)nn2C)OCC)C
• InChI: InChI=1S/C47H62N12O11S2/c1-7-11-35-39-41(54(5)52-35)45(60)50-43(48-39)33-29-31(13-15-37(33)67-9-3)71(63,64)58-21-17-56(18-22-58)25-27-69-47(62)70-28-26-57-19-23-59(24-20-57)72(65,66)32-14-16-38(68-10-4)34(30-32)44-49-40-36(12-8-2)53-55(6)42(40)46(61)51-44/h13-16,29-30H,7-12,17-28H2,1-6H3,(H,48,50,60)(H,49,51,61)
• InChIKey: MVYUCRDXZXLFSB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis{2-[4-(4-ethoxy-3-{1-methyl-7-oxo-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-5-yl}benzenesulfonyl)piperazin-1-yl]ethyl} carbonate
• IUPAC Traditional name: lodenafil
• Synonyms: 5,5'-[Carbonylbis[oxy-2,1-ethanediyl-4,1-piperazinediylsulfonyl(6-ethoxy-3,1-phenylene)]]bis[1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one; 4-[[3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-1-piperazineethanol Carbonate Ester; Lodenafil Carbonate

Database IDs

• CAS Number: 398507-55-6
• PubChem SID: 164228269
• PubChem CID: 9963284

CALCULATED PROPERTIES

• Acid pKa: 6.957903
• H Acceptors: 18
• H Donor: 2
• LogD (pH = 5.5): 3.586221
• LogD (pH = 7.4): 3.224313
• Log P: 3.770439
• Molar Refractivity: 293.9794 cm^3
• Polarizability: 103.3442 Å^3
• Polar Surface Area: 253.79 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L469300

Lodenafil carbonate is a new PDE-5 inhibitor used for oral therapy in erectile dysfunction.

REFERENCES

• Rosen, R., et al.: Urology, 49, 822 (1997)
• Chew, K., et al.: J. Sex Med., 5, 928 (1997)
• Teixeira, C., et al.: Eur. J. Pharmacol., 591, 189 (1997)