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Sidenafil Citrate (Tadalafil)

Sildenafil , sold as Viagra and other trade names, is a medication used to treat erectile dysfunction and pulmonary arterial hypertension. Its effectiveness for treating sexual dysfunction in women has not been demonstrated.

Common side effects include headaches and heart burn, as well as flushed skin. Caution is advised in those who have cardiovascular disease. Rare but serious side effects include prolonged erections, which can lead to damage to the penis, and sudden-onset hearing loss. Sildenafil should not be taken by people who take nitrates such as nitroglycerin, as this may result in a severe and potentially fatal drop in blood pressure.

It acts by inhibiting cGMP-specific phosphodiesterase type 5 (PDE5), an enzyme that promotes degradation of cGMP, which regulates blood flow in the penis.

It was originally discovered by Pfizer scientists Andrew Bell, David Brown, and Nicholas Terrett. Since becoming available in 1998, sildenafil has been a common treatment for erectile dysfunction; its primary competitors are tadalafil (Cialis) and vardenafil (Levitra).

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Product Description



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


Trade names Viagra, Revatio, others
AHFS/Drugs.com monograph
MedlinePlus a699015
Licence data EMA:Link, US FDA:link
Pregnancy category
  • US: B (No risk in non-human studies)
Legal status
  • Rx-only[where?]
Routes of administration Oral, IV


Bioavailability 40%
Metabolism Hepatic (mostly CYP3A4, also CYP2C9)
Biological half-life 3 to 4 hours
Excretion Fecal (80%) and renal (around 13%)


CAS Number 139755-83-2 
ATC code G04BE03
PubChem CID: 5281023
DrugBank DB00203 
ChemSpider 56586 
UNII 3M7OB98Y7H 
KEGG D08514 
ChEBI CHEBI:58987 
ChEMBL CHEMBL1737 
PDB ligand ID VIA (PDBe, RCSB PDB)


Formula C22H30N6O4S
Molecular mass base: 474.6 g/mol

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