sildenafil   

GtoPdb Ligand ID: 4743

Synonyms: Viagra®
sildenafil is an approved drug (EMA & FDA (1998))
Compound class: Synthetic organic
Comment: Sildenafil is a phosphodiesterase type 5 (PDE5) inhibitor.
Marketed formulations may contain ildenafil citrate (PubChem CID 62853).
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 121.8
Molecular weight 474.2
XLogP 3.11
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCCc1nn(c2c1[nH]c(nc2=O)c1cc(ccc1OCC)S(=O)(=O)N1CCN(CC1)C)C
Isomeric SMILES CCCc1nn(c2c1[nH]c(nc2=O)c1cc(ccc1OCC)S(=O)(=O)N1CCN(CC1)C)C
InChI InChI=1S/C22H30N6O4S/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)
InChI Key BNRNXUUZRGQAQC-UHFFFAOYSA-N
No information available.
Summary of Clinical Use
Used in the treatment of erectile dysfunction (ED) and pulmonary arterial hypertension (PAH, under brand name Revatio®).
Mechanism Of Action and Pharmacodynamic Effects
Sildenafil is a selective phosphodiesterase type 5 (PDE5) inhibitor. Such inhibitors block the degradative action of PDE5 on cGMP in the smooth muscle cells lining the blood vessels supplying the corpus cavernosum of the penis. This action dilates these blood vessels allowing blood ingress and leads to functional erection.
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