Sildenafil
| Clinical data | |
|---|---|
| Pronunciation | /sɪlˈdɛnəfɪl/ sil-DEN-ə-fil |
| Trade names | Viagra, others |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a699015 |
| License data |
|
| Pregnancy category |
|
| Routes of administration | By mouth, sublingual, intravenous |
| Drug class | PDE5 inhibitor |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Bioavailability | 41% (mean)[8] |
| Protein binding | ~96% |
| Metabolism | Liver: CYP3A4 (major route), CYP2C9 (minor route) |
| Metabolites | N-desmethylsildenafil (~50% potency for PDE5) |
| Onset of action | 20 minutes |
| Elimination half-life | 3–4 hours |
| Excretion | Feces (~80%), urine (~13%)[5] |
| Identifiers | |
IUPAC name
| |
| CAS Number |
|
| PubChem CID | |
| DrugBank |
|
| ChemSpider | |
| UNII |
|
| KEGG | |
| ChEBI |
|
| ChEMBL |
|
| PDB ligand | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.122.676 |
| Chemical and physical data | |
| Formula | C22H30N6O4S |
| Molar mass | 474.58 g·mol−1 |
| 3D model (JSmol) | |
SMILES
| |
InChI
| |
| (what is this?) (verify) | |
Sildenafil, sold under the brand name Viagra among others, is a medication used to treat erectile dysfunction and pulmonary arterial hypertension.[5][9] It is also sometimes used off-label for the treatment of certain symptoms in secondary Raynaud's phenomenon.[10] It is unclear if it is effective for treating sexual dysfunction in females.[9] It can be taken orally (swallowed by mouth), intravenously (injection into a vein), or through the sublingual route (dissolved under the tongue).[9][11] Onset when taken orally is typically within twenty minutes and lasts for about two hours.[9]
Common side effects include headaches, heartburn, and flushed skin.[9] Caution is advised in those with cardiovascular disease.[9] Rare but serious side effects include vision problems, hearing loss, and prolonged erection (priapism) that can lead to damage to the penis.[9] Sildenafil should not be taken by people on nitric oxide donors such as nitroglycerin, as this may result in a serious drop in blood pressure.[9]
Sildenafil acts by blocking phosphodiesterase 5 (PDE5), an enzyme that promotes breakdown of cGMP, which regulates blood flow in the penis.[9] It requires sexual arousal to work, and does not by itself cause or increase sexual arousal.[9] It also results in dilation of the blood vessels in the lungs.[9]
Pfizer originally discovered the medication in 1989 while looking for a treatment for angina.[12] It was approved for medical use in the United States and in the European Union in 1998.[6][9][12][13] In 2022, it was the 157th most commonly prescribed medication in the United States, with more than 3 million prescriptions.[14][15] It is available as a generic medication.[16][17] In the United Kingdom, it is available over-the-counter (OTC).[18]
- ^ "Sildenafil Use During Pregnancy". Drugs.com. 7 October 2019. Archived from the original on 12 October 2020. Retrieved 6 October 2020.
- ^ "MHRA reclassifies Viagra Connect tablets to a Pharmacy medicine".
- ^ "Viagra can be sold over the counter". BBC News. 28 November 2017.
- ^ "Viagra to be available without prescription in UK". CNN. 28 November 2017.
- ^ a b c Cite error: The named reference
Viagra FDA labelwas invoked but never defined (see the help page). - ^ a b "Viagra EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 11 October 2020. Retrieved 6 October 2020.
- ^ "Revatio EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 11 November 2020. Retrieved 6 October 2020.
- ^ Nichols DJ, Muirhead GJ, Harness JA (6 March 2002). "Pharmacokinetics of sildenafil after single oral doses in healthy male subjects: absolute bioavailability, food effects and dose proportionality". British Journal of Clinical Pharmacology. 53 (Suppl 1): 5S – 12S. doi:10.1046/j.0306-5251.2001.00027.x. PMC 1874258. PMID 11879254.
- ^ a b c d e f g h i j k l "Sildenafil Citrate". The American Society of Health-System Pharmacists. Archived from the original on 23 April 2020. Retrieved 1 December 2014.
- ^ Cite error: The named reference
Raynaud's treatment - sildenafil + other PDE5 inhibitorswas invoked but never defined (see the help page). - ^ Cite error: The named reference
sublingualwas invoked but never defined (see the help page). - ^ a b Goldstein I, Burnett AL, Rosen RC, Park PW, Stecher VJ (January 2019). "The Serendipitous Story of Sildenafil: An Unexpected Oral Therapy for Erectile Dysfunction". Sexual Medicine Reviews. 7 (1): 115–128. doi:10.1016/j.sxmr.2018.06.005. PMID 30301707. S2CID 52945888.
- ^ "Drug Approval Package: Viagra (sildenafil citrate) NDA #020895". U.S. Food and Drug Administration (FDA). 27 March 1998. Archived from the original on 31 March 2021. Retrieved 15 February 2021.
- ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
- ^ "Sildenafil Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
- ^ Gordon S (11 December 2017). "Generic Viagra: Two versions of sildenafil hit the market today". CBS News. Archived from the original on 25 November 2018. Retrieved 24 November 2018.
- ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 3 March 2023. Archived from the original on 12 February 2022. Retrieved 6 March 2023.
- ^ LaMattina J. "With Viagra Now Available Over-The-Counter In The U.K., Will The U.S. Follow Suit?". Forbes. Archived from the original on 25 November 2018. Retrieved 24 November 2018.