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
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)
1. Sager G, Ørvoll EØ, Lysaa RA, Kufareva I, Abagyan R, Ravna AW. (2012)
Novel cGMP efflux inhibitors identified by virtual ligand screening (VLS) and confirmed by experimental studies.
J. Med. Chem., 55 (7): 3049-57. [PMID:22380603]
2. Treiber A, Schneiter R, Häusler S, Stieger B. (2007)
Bosentan is a substrate of human OATP1B1 and OATP1B3: inhibition of hepatic uptake as the common mechanism of its interactions with cyclosporin A, rifampicin, and sildenafil.
Drug Metab. Dispos., 35 (8): 1400-7. [PMID:17496208]
3. Turko IV, Ballard SA, Francis SH, Corbin JD. (1999)
Inhibition of cyclic GMP-binding cyclic GMP-specific phosphodiesterase (Type 5) by sildenafil and related compounds.
Mol. Pharmacol., 56 (1): 124-30. [PMID:10385692]
4. Wang G, Liu Z, Chen T, Wang Z, Yang H, Zheng M, Ren J, Tian G, Yang X, Li L et al.. (2012)
Design, synthesis, and pharmacological evaluation of monocyclic pyrimidinones as novel inhibitors of PDE5.
J. Med. Chem., 55 (23): 10540-50. [PMID:23137303]