Molecule Details
| InChIKey | BNRNXUUZRGQAQC-UHFFFAOYSA-N |
|---|---|
| Compound Name | Sildenafil |
| Canonical SMILES | CCCc1nn(C)c2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCN(C)CC4)ccc3OCC)nc12 |
| Clinical Status | Data-mined Candidate |
| Targets (Human+Pathogen) | 12 |
| Pfam Stratification | Cross-Family |
| Avg pChEMBL | 7.15 |
| Source | ChEMBL;BindingDB |
2D Structure
Activity Profile
DrugBank Annotations
| DrugBank ID | DB00203 |
|---|---|
| Drug Name | Sildenafil |
| CAS Number | 139755-83-2 |
| Groups | approved investigational |
| ATC Codes | G01AE10 G04BE03 |
| Description | In eliciting its mechanism of action, sildenafil ultimately prevents or minimizes the breakdown of cyclic guanosine monophosphate (cGMP) by inhibiting cGMP specific phosphodiesterase type 5 (PDE5) [F3850, F3853, F3856, F3859, F3883, F3886, L5611, L5614]. The result of doing so allows cGMP present in... |
Categories: Agents Causing Muscle Toxicity Amides Cardiovascular Agents Cytochrome P-450 CYP2C19 Inhibitors Cytochrome P-450 CYP2C19 Inhibitors (weak) Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (weak) Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP2E1 Inhibitors Cytochrome P-450 CYP2E1 Inhibitors (strength unknown) Cytochrome P-450 CYP2E1 Substrates Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Drugs Used in Erectile Dysfunction Enzyme Inhibitors Genitourinary Agents Heterocyclic Compounds, Fused-Ring OATP1B1/SLCO1B1 Inhibitors P-glycoprotein inhibitors P-glycoprotein substrates Phosphodiesterase 5 Inhibitors Phosphodiesterase Inhibitors Piperazines Purines Sulfonamides Sulfones Sulfur Compounds Urological Agents Urologicals Vasodilating Agents
Cross-references: BindingDB: 50238854 ChEBI: 9139 CHEMBL192 ChemSpider: 5023 Drugs Product Database (DPD): 11854 C07259 D08514 PDB: VIA PharmGKB: PA451346 PubChem:5212 PubChem:46508371 RxCUI: 136411 Therapeutic Targets Database: DAP000614 Wikipedia: Sildenafil ZINC: ZINC000019796168
Target Activities (12)
| Target | Gene | Organism | Category | Pfam | pChEMBL | Type | Source |
|---|---|---|---|---|---|---|---|
| O76074 | PDE5A | Homo sapiens | Human | PF01590 PF00233 | 8.5 | IC50 | ChEMBL;BindingDB |
| O43924 | PDE6D | Homo sapiens | Human | PF05351 | 7.6 | IC50 | ChEMBL |
| P16499 | PDE6A | Homo sapiens | Human | PF01590 PF00233 | 7.6 | IC50 | ChEMBL |
| P18545 | PDE6G | Homo sapiens | Human | PF04868 | 7.6 | IC50 | ChEMBL |
| P35913 | PDE6B | Homo sapiens | Human | PF01590 PF00233 | 7.6 | IC50 | ChEMBL |
| Q13956 | PDE6H | Homo sapiens | Human | PF04868 | 7.6 | IC50 | ChEMBL |
| P51160 | PDE6C | Homo sapiens | Human | PF01590 PF00233 | 7.4 | IC50 | ChEMBL;BindingDB |
| P29274 | ADORA2A | Homo sapiens | Human | PF00001 | 6.7 | Ki | ChEMBL;BindingDB |
| Q01064 | PDE1B | Homo sapiens | Human | PF00233 PF08499 | 6.4 | IC50 | ChEMBL;BindingDB |
| Q14123 | PDE1C | Homo sapiens | Human | PF00233 PF08499 | 6.4 | IC50 | ChEMBL |
| P54750 | PDE1A | Homo sapiens | Human | PF00233 PF08499 | 6.3 | IC50 | ChEMBL;BindingDB |
| P30542 | ADORA1 | Homo sapiens | Human | PF00001 | 6.1 | Ki | ChEMBL |
DrugBank Target Actions (22)
| Target | Gene | Target Name | Action | Type |
|---|---|---|---|---|
| P05181 | CYP2E1 | Cytochrome P450 2E1 | inhibitor | enzymes |
| P11712 | CYP2C9 | Cytochrome P450 2C9 | inhibitor | enzymes |
| P33261 | CYP2C19 | Cytochrome P450 2C19 | inhibitor | enzymes |
| P05181 | CYP2E1 | Cytochrome P450 2E1 | substrate | enzymes |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | substrate | enzymes |
| P10635 | CYP2D6 | Cytochrome P450 2D6 | substrate | enzymes |
| P11712 | CYP2C9 | Cytochrome P450 2C9 | substrate | enzymes |
| P20815 | CYP3A5 | Cytochrome P450 3A5 | substrate | enzymes |
| P24462 | CYP3A7 | Cytochrome P450 3A7 | substrate | enzymes |
| P33261 | CYP2C19 | Cytochrome P450 2C19 | substrate | enzymes |
| P11926 | P11926 | Ornithine decarboxylase | downregulator | targets |
| Q9NZQ7 | CD274 | Programmed cell death 1 ligand 1 | downregulator | targets |
| O76074 | PDE5A | cGMP-specific 3',5'-cyclic phosphodiesterase | inhibitor | targets |
| P18545 | PDE6G | Retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma | inhibitor | targets |
| Q13956 | PDE6H | Retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma | inhibitor | targets |
| P05155 | P05155 | Plasma protease C1 inhibitor | modulator | targets |
| O15439 | O15439 | ATP-binding cassette sub-family C member 4 | inhibitor | transporters |
| O15440 | O15440 | ATP-binding cassette sub-family C member 5 | inhibitor | transporters |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | inhibitor | transporters |
| Q5T3U5 | Q5T3U5 | ATP-binding cassette sub-family C member 10 | inhibitor | transporters |
| Q9Y6L6 | SLCO1B1 | Solute carrier organic anion transporter family member 1B1 | inhibitor | transporters |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | substrate | transporters |