tadalafil   Click here for help

GtoPdb Ligand ID: 7299

Synonyms: Adcirca® | Cialis® | IC-351 | IC351
Approved drug PDB Ligand
tadalafil is an approved drug (EMA (2002), FDA (2003))
Compound class: Synthetic organic
Comment: Tadafil is a phosphodiesterase type 5 (PDE5) inhibitor.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 74.87
Molecular weight 389.14
XLogP 1.75
No. Lipinski's rules broken 0
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Canonical SMILES O=C1N(C)CC(=O)N2C1Cc1c(C2c2ccc3c(c2)OCO3)[nH]c2c1cccc2
Isomeric SMILES O=C1N(C)CC(=O)N2[C@@H]1Cc1c([C@H]2c2ccc3c(c2)OCO3)[nH]c2c1cccc2
InChI InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1
1. Forgue ST, Patterson BE, Bedding AW, Payne CD, Phillips DL, Wrishko RE, Mitchell MI. (2006)
Tadalafil pharmacokinetics in healthy subjects.
Br J Clin Pharmacol, 61 (3): 280-8. [PMID:16487221]
2. Mohamed HA, Girgis NM, Wilcken R, Bauer MR, Tinsley HN, Gary BD, Piazza GA, Boeckler FM, Abadi AH. (2011)
Synthesis and molecular modeling of novel tetrahydro-β-carboline derivatives with phosphodiesterase 5 inhibitory and anticancer properties.
J Med Chem, 54 (2): 495-509. [PMID:21189023]