GtoPdb Ligand ID: 9552

Compound class: Synthetic organic
Comment: Nitrosoprodenafil is a novel nitrosated analogue of the PDE5 inhibitor sildenafil, that acts as a prodrug releasing aildenafil (methisosildenafil; PubChem CID 16721107) and NO [1]. NO-induced effects on vasodilation are synergistic with inhibition of PDE5 action. This type of compound has been avoided by conventional pharmaceutical companies because of the serious risk of causing a life-threatening drop in blood pressure, and because of the hepatotoxicity of nitrosamines.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 190.41
Molecular weight 628.23
XLogP 3.53
No. Lipinski's rules broken 1
Canonical SMILES CCCc1nn(c2c1nc(nc2Oc1ncc(s1)N(N=O)C)c1cc(ccc1OCC)S(=O)(=O)C1CC(C)NC(C1)C)C
Isomeric SMILES CCCc1nn(c2c1nc(nc2Oc1ncc(s1)N(N=O)C)c1cc(ccc1OCC)S(=O)(=O)C1CC(C)NC(C1)C)C
InChI InChI=1S/C28H36N8O5S2/c1-7-9-21-24-25(36(6)33-21)27(41-28-29-15-23(42-28)35(5)34-37)32-26(31-24)20-14-18(10-11-22(20)40-8-2)43(38,39)19-12-16(3)30-17(4)13-19/h10-11,14-17,19,30H,7-9,12-13H2,1-6H3
1. Venhuis BJ, Zomer G, Hamzink M, Meiring HD, Aubin Y, de Kaste D. (2011)
The identification of a nitrosated prodrug of the PDE-5 inhibitor aildenafil in a dietary supplement: a Viagra with a pop.
J Pharm Biomed Anal, 54 (4): 735-41. [PMID:21145686]