riociguat   Click here for help

GtoPdb Ligand ID: 5257

Synonyms: Adempas® | BAY 63-2521
Approved drug PDB Ligand
riociguat is an approved drug (FDA (2013), EMA (2014))
Compound class: Synthetic organic
Comment: Riociguat is the first-in-class stimulator of soluble guanylate cyclase (sGC) class of drugs.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 138.07
Molecular weight 422.16
XLogP 2.34
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES COC(=O)N(c1c(N)nc(nc1N)c1nn(c2c1cccn2)Cc1ccccc1F)C
Isomeric SMILES COC(=O)N(c1c(N)nc(nc1N)c1nn(c2c1cccn2)Cc1ccccc1F)C
InChI InChI=1S/C20H19FN8O2/c1-28(20(30)31-2)15-16(22)25-18(26-17(15)23)14-12-7-5-9-24-19(12)29(27-14)10-11-6-3-4-8-13(11)21/h3-9H,10H2,1-2H3,(H4,22,23,25,26)
No information available.
Summary of Clinical Use Click here for help
Riociguat is approved to treat persistent or recurrent chronic thromboembolic pulmonary hypertension and pulmonary arterial hypertension. This drug was approved following assessment within the US FDA orphan and priority review process.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Riociguat activates soluble guanylyl cyclase (sGC), a heterodimeric enzyme comprising α and β chains. The genes and proteins for the enzyme subunits are listed in this database, in the Soluble guanylyl cyclase family. sGC is a receptor for nitric oxide (NO), activation of which increases biosynthesis of cyclic GMP and this leads to vasodilation.
External links Click here for help