<Table> Sildenafil <Tr> <Td_colspan="2"> </Td> </Tr> <Tr> <Td_colspan="2"> </Td> </Tr> <Tr> <Th_colspan="2"> Clinical data </Th> </Tr> <Tr> <Th> Pronunciation </Th> <Td> / sɪlˈdɛnəfɪl / sil - DEN - ə - fil </Td> </Tr> <Tr> <Th> Trade names </Th> <Td> Viagra, Revatio, others </Td> </Tr> <Tr> <Th> AHFS / Drugs.com </Th> <Td> Monograph </Td> </Tr> <Tr> <Th> MedlinePlus </Th> <Td> a699015 </Td> </Tr> <Tr> <Th> License data </Th> <Td> <Ul> <Li> EU EMA: by INN </Li> <Li> US FDA: Sildenafil </Li> </Ul> </Td> </Tr> <Tr> <Th> Pregnancy category </Th> <Td> <Ul> <Li> AU: B1 </Li> <Li> US: B (No risk in non-human studies) </Li> </Ul> <Ul> <Li> </Li> </Ul> </Td> </Tr> <Tr> <Th> Routes of administration </Th> <Td> By mouth (tablets), IV </Td> </Tr> <Tr> <Th> ATC code </Th> <Td> <Ul> <Li> G04BE03 (WHO) </Li> </Ul> </Td> </Tr> <Tr> <Th_colspan="2"> Legal status </Th> </Tr> <Tr> <Th> Legal status </Th> <Td> <Ul> <Li> AU: S4 (Prescription only) </Li> <Li> CA: ℞ - only </Li> <Li> UK: POM (Prescription only) </Li> <Li> US: ℞ - only </Li> <Li> In general: ℞ (Prescription only) </Li> </Ul> </Td> </Tr> <Tr> <Th_colspan="2"> Pharmacokinetic data </Th> </Tr> <Tr> <Th> Bioavailability </Th> <Td> 41% (mean) </Td> </Tr> <Tr> <Th> Protein binding </Th> <Td> ~ 96% </Td> </Tr> <Tr> <Th> Metabolism </Th> <Td> Liver: CYP3A4 (major route), CYP2C9 (minor route) </Td> </Tr> <Tr> <Th> Metabolites </Th> <Td> N - desmethylsildenafil (~ 50% potency for PDE) </Td> </Tr> <Tr> <Th> Biological half - life </Th> <Td> 3--4 hours </Td> </Tr> <Tr> <Th> Excretion </Th> <Td> Feces (~ 80%), urine (~ 13%) </Td> </Tr> <Tr> <Th_colspan="2"> Identifiers </Th> </Tr> <Tr> <Td_colspan="2"> IUPAC name (show) <Ul> <Li> 5 - (2 - Ethoxy - 5 - ((4 - methylpiperazin - 1 - yl) sulfonyl) phenyl) - 1 - methyl - 3 - propyl - 1H, 6H, 7H - pyrazolo (4, 3 - d) pyrimidin - 7 - one </Li> </Ul> </Td> </Tr> <Tr> <Th> CAS Number </Th> <Td> <Ul> <Li> 139755 - 83 - 2 </Li> <Li> Citrate: 171599 - 83 - 0 </Li> </Ul> </Td> </Tr> <Tr> <Th> PubChem CID </Th> <Td> <Ul> <Li> 5212 </Li> </Ul> </Td> </Tr> <Tr> <Th> DrugBank </Th> <Td> <Ul> <Li> DB00203 </Li> </Ul> </Td> </Tr> <Tr> <Th> ChemSpider </Th> <Td> <Ul> <Li> 5023 </Li> </Ul> </Td> </Tr> <Tr> <Th> UNII </Th> <Td> <Ul> <Li> 3M7OB98Y7H </Li> </Ul> </Td> </Tr> <Tr> <Th> KEGG </Th> <Td> <Ul> <Li> D08514 </Li> </Ul> </Td> </Tr> <Tr> <Th> ChEBI </Th> <Td> <Ul> <Li> CHEBI: 9139 </Li> </Ul> </Td> </Tr> <Tr> <Th> ChEMBL </Th> <Td> <Ul> <Li> CHEMBL192 </Li> </Ul> </Td> </Tr> <Tr> <Th> PDB ligand </Th> <Td> <Ul> <Li> VIA (PDBe, RCSB PDB) </Li> </Ul> </Td> </Tr> <Tr> <Th> ECHA InfoCard </Th> <Td> 100.122. 676 </Td> </Tr> <Tr> <Th_colspan="2"> Chemical and physical data </Th> </Tr> <Tr> <Th> Formula </Th> <Td> </Td> </Tr> <Tr> <Th> Molar mass </Th> <Td> 474.5764 g / mol </Td> </Tr> <Tr> <Th> 3D model (JSmol) </Th> <Td> <Ul> <Li> Interactive image </Li> </Ul> </Td> </Tr> <Tr> <Td_colspan="2"> SMILES (show) <Ul> <Li> CCCC1 = NN (C2 = C1NC (= NC2 = O) C3 = C (C = CC (= C3) S (= O) (= O) N4CCN (CC4) C) OCC) C </Li> </Ul> </Td> </Tr> <Tr> <Td_colspan="2"> InChI (show) <Ul> <Li> 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) </Li> <Li> Key: BNRNXUUZRGQAQC - UHFFFAOYSA - N </Li> </Ul> </Td> </Tr> <Tr> <Th_colspan="2"> (what is this?) (verify) </Th> </Tr> </Table> <Tr> <Th_colspan="2"> Clinical data </Th> </Tr> <Tr> <Th> Pronunciation </Th> <Td> / sɪlˈdɛnəfɪl / sil - DEN - ə - fil </Td> </Tr>

S i l d e n a f i l