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
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
phosphodiesterase 5A Hs Inhibitor Inhibition 8.4 – 9.0 pIC50 - 3-4
pIC50 8.4 – 9.0 (IC50 3.9x10-9 – 1x10-9 M) [3-4]
phosphodiesterase 6C Hs Inhibitor Inhibition 7.4 pIC50 - 4
pIC50 7.4 (IC50 3.92x10-8 M) [4]
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
ABCC5 Hs Inhibitor Inhibition 5.9 pKi - 1
pKi 5.9 (Ki 1.2x10-6 M) [1]
OATP1B3 Hs Inhibitor Inhibition 6.1 pIC50 - 2
pIC50 6.1 (IC50 8x10-7 M) [2]
OATP2B1 Hs Inhibitor Inhibition - - - 2
[2]
Description: Inhibition only observed at sildenafil concentrations above those achieved in therapeutic use.
Ligand mentioned in the following text fields