Sildenafil

Sildenafil, sold under the brand name Viagra, among others, is a medication used to treat erectile dysfunction and pulmonary arterial hypertension. It is also sometimes used off-label for the treatment of certain symptoms in secondary Raynaud's phenomenon. It is unclear if it is effective for treating sexual dysfunction in females. It can be taken orally (swallowed by mouth), intravenously (injection into a vein), or through the sublingual route (dissolved under the tongue). Onset when taken orally is typically within twenty minutes and lasts for about two hours.

Sildenafil
Clinical data
Pronunciation/sɪlˈdɛnəfɪl/ sil-DEN-ə-fil
Trade namesViagra, Revatio, others
AHFS/Drugs.comMonograph
MedlinePlusa699015
License data
Pregnancy
category
  • AU: B1
Routes of
administration
Oral (tablets), intravenous, sublingual
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability41% (mean)
Protein binding~96%
MetabolismLiver: CYP3A4 (major route), CYP2C9 (minor route)
MetabolitesN-desmethylsildenafil (~50% potency for PDE5)
Onset of action20 minutes
Elimination half-life3–4 hours
ExcretionFeces (~80%), urine (~13%)
Identifiers
  • 5-{2-Ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,6-dihydro-6H-pyrazolo[4,3-d]pyrimidin-7-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.122.676
Chemical and physical data
FormulaC22H30N6O4S
Molar mass474.58 g·mol−1
3D model (JSmol)
  • CCCC1=NN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)C)OCC)C
  • 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) N
  • Key:BNRNXUUZRGQAQC-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

Common side effects include headaches, heartburn, and flushed skin. Caution is advised in those with cardiovascular disease. Rare but serious side effects include vision problems, hearing loss, and prolonged erection (priapism) that can lead to damage to the penis. Sildenafil should not be taken by people on nitrates such as nitroglycerin (glycerin trinitrate), as this may result in a serious drop in blood pressure. Sildenafil should not be taken within four hours of taking an alpha blocker.

Sildenafil acts by blocking phosphodiesterase 5 (PDE5), an enzyme that promotes breakdown of cGMP, which regulates blood flow in the penis. It requires sexual arousal to work, and does not by itself cause or increase sexual arousal. It also results in dilation of the blood vessels in the lungs.

Pfizer originally discovered the medication in 1989 while looking for a treatment for angina. It was approved for medical use in the United States and in the European Union in 1998. In 2020, it was the 183rd most commonly prescribed medication in the United States, with more than 2 million prescriptions. It is available as a generic medication. In the United Kingdom, it is available over the counter. Most of the active pharmaceutical ingredient, sildenafil citrate, is produced in Pfizer's Ringaskiddy complex in County Cork, Ireland, which is Pfizer's largest production facility outside of the United States.

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