Sildenafil



Sildenafil.svg
Sildenafil-from-xtal-3D-balls.png
Systematic (IUPAC) name
1-[4-ethoxy-3-(6,7-dihydro-1-methyl-
7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)
phenylsulfonyl]-4-methylpiperazine
Clinical data
Trade names Viagra
AHFS/Drugs.com monograph
MedlinePlus a699015
Licence data EMA:Link, US FDA:link
Pregnancy cat.
Legal status
  • Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability 40%
Metabolism Hepatic (mostly CYP3A4, also CYP2C9)
Half-life 3 to 4 hours
Excretion Fecal (80%) and renal (around 13%)
Identifiers
CAS number 139755-83-2 Yes
ATC code G04BE03
PubChem CID 5281023
DrugBank DB00203
ChemSpider 56586 Yes
UNII 3M7OB98Y7H Yes
KEGG D08514 Yes
ChEBI CHEBI:58987 Yes
ChEMBL CHEMBL1737 
PDB ligand ID VIA (PDBe, RCSB PDB)
Chemical data
Formula C22H30N6O4S 
Mol. mass base: 474.6 g/mol
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Sildenafil citrate, sold as Viagra, Revatio and under various other trade names, is a drug used to treat erectile dysfunction and pulmonary arterial hypertension (PAH). It was originally discovered by Pfizer scientists Andrew Bell, David Brown, and Nicholas Terrett.[1][2] It acts by inhibiting cGMP-specific phosphodiesterase type 5 (PDE5), an enzyme that promotes degradation of cGMP, which regulates blood flow in the penis. Since becoming available in 1998, sildenafil has been the prime treatment for erectile dysfunction; its primary competitors on the market are tadalafil (Cialis) and vardenafil (Levitra).