nitrosoprodenafil   Click here for help

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
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-[2-[5-[5-(2,6-dimethylpiperidin-4-yl)sulfonyl-2-ethoxyphenyl]-1-methyl-3-propylpyrazolo[4,3-d]pyrimidin-7-yl]oxy-1,3-thiazol-5-yl]-N-methylnitrous amide
Database Links Click here for help
GtoPdb PubChem SID 336446938
PubChem CID 71308247
Search Google for chemical match using the InChIKey BNIFBESUYAAZKT-UHFFFAOYSA-N
Search Google for chemicals with the same backbone BNIFBESUYAAZKT
UniChem Compound Search for chemical match using the InChIKey BNIFBESUYAAZKT-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey BNIFBESUYAAZKT-UHFFFAOYSA-N