# Avanafil > Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Avanafil > Markdown URL: https://mediated.wiki/source/Avanafil.md > Source: https://en.wikipedia.org/wiki/Avanafil > Source revision: 1355894730 > License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) {{Short description|Chemical compound}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 447824430 | image = Avanafil.svg | image_class = skin-invert-image | alt = | image2 = Avanafil ball-and-stick.png | image_class2 = bg-transparent | alt2 = | caption = Avanafil is a [PDE5 inhibitor](/source/PDE5_inhibitor) | tradename = Stendra | Drugs.com = {{drugs.com|monograph|avanafil}} | MedlinePlus = a614010 | licence_EU = yes | DailyMedID = Avanafil | licence_US = Avanafil | pregnancy_AU = | pregnancy_US = | routes_of_administration = [By mouth](/source/Oral_administration) | ATC_prefix = G04 | ATC_suffix = BE10 | legal_AU = S4 | legal_AU_comment = {{cite web | title=Prescription medicines: registration of new chemical entities in Australia, 2016 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/prescription-medicines-registration-new-chemical-entities-australia-2016 | access-date=10 April 2023}} | legal_CA = | legal_UK = POM | legal_US = Rx-only | legal_EU = Rx-only | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 330784-47-9 | PubChem = 9869929 | IUPHAR_ligand = 7448 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB06237 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 8045620 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = DR5S136IVO | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D03217 | ChEBI = 66876 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1963681 | NIAID_ChemDB = | PDB_ligand = E6L | synonyms = | IUPAC_name = (''S'')-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-''N''-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide | C = 23 | H = 26 | Cl = 1 | N = 7 | O = 3 | smiles = Clc1c(OC)ccc(c1)CNc3nc(ncc3C(=O)NCc2ncccn2)N4[C@@H](CCC4)CO | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = WEAJZXNPAWBCOA-INIZCTEOSA-N }} '''Avanafil''' is a [PDE5 inhibitor](/source/PDE5_inhibitor) approved for [erectile dysfunction](/source/erectile_dysfunction) by the [FDA](/source/FDA) on April 27, 2012{{cite web |url=https://www.drugs.com/history/stendra.html |title=Stendra FDA Approval History |author= |publisher=Drugs.com |access-date=6 March 2021}} and by EMA on June 21, 2013.{{cite web| url=http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/medicines/002581/human_med_001661.jsp&mid=WC0b01ac058001d124| title=Spedra (avanafil)| publisher=European Medicines Agency| access-date=17 April 2014| archive-date=1 April 2014| archive-url=https://web.archive.org/web/20140401111423/http://www.ema.europa.eu/ema/index.jsp?curl=pages%2Fmedicines%2Fhuman%2Fmedicines%2F002581%2Fhuman_med_001661.jsp&mid=WC0b01ac058001d124| url-status=dead}} Avanafil is sold under the brand names '''Stendra''' and '''Spedra'''. It was invented at Mitsubishi Tanabe Pharma, formerly known as Tanabe Seiyaku Co., and licensed to [Vivus Inc.](/source/Vivus), which partnered with [Menarini Group](/source/Menarini) to commercialise Spedra in over forty European countries, Australia, and New Zealand.{{cite web | title = VIVUS Announces Avanafil Partnership With Menarini | publisher = Vivus Inc |url=http://ir.vivus.com/releasedetail.cfm?releaseid=775706 |archive-url=https://web.archive.org/web/20151208155146/http://ir.vivus.com/releasedetail.cfm?ReleaseID=775706 |archive-date=2015-12-08 |url-status=dead }} Metuchen Pharmaceuticals obtained exclusive rights within the United States.{{cite web | title = VIVUS and Metuchen Pharmaceuticals Announce License Agreement for Commercial Rights to Stendra | url = http://ir.vivus.com/news-releases/news-release-details/vivus-and-metuchen-pharmaceuticals-announce-license-agreement | archive-url = https://web.archive.org/web/20221129030618/http://ir.vivus.com/news-releases/news-release-details/vivus-and-metuchen-pharmaceuticals-announce-license-agreement | archive-date = 29 November 2022 | publisher = Vivus Inc | date = 3 October 2016 }} Avanafil acts by inhibiting a specific [phosphodiesterase](/source/phosphodiesterase) type 5 enzyme found in various body tissues, primarily in the [corpus cavernosum penis](/source/corpus_cavernosum_penis).{{cite web| url=http://www.medicinenet.com/avanafil_stendra/article.htm | publisher = Medicine Net | access-date = 17 April 2014 | title= avanafil, Spedra }} Other similar drugs are [sildenafil](/source/sildenafil), [tadalafil](/source/tadalafil) and [vardenafil](/source/vardenafil). The advantage of avanafil is that it has very fast [onset of action](/source/onset_of_action) compared with other PDE5 inhibitors. It is absorbed quickly, reaching a maximum serum concentration in about thirty to forty-five minutes.{{cite journal | vauthors = Kyle JA, Brown DA, Hill JK | title = Avanafil for erectile dysfunction | journal = The Annals of Pharmacotherapy | volume = 47 | issue = 10 | pages = 1312–1320 | date = October 2013 | pmid = 24259695 | doi = 10.1177/1060028013501989 | publisher = Sage Publishing | s2cid = 6562049 }} About two-thirds of the participants were able to engage in [sexual activity](/source/sexual_activity) within fifteen minutes. == Medical use == Avanafil is used to treat erectile dysfunction (ED).{{cite journal | vauthors = Burke RM, Evans JD | title = Avanafil for treatment of erectile dysfunction: review of its potential | journal = Vascular Health and Risk Management | volume = 8 | issue = | pages = 517–523 | date = 2012 | pmid = 22973106 | pmc = 3433322 | doi = 10.2147/VHRM.S26712 | doi-access = free }} == Adverse effects == Although avanafil is generally well tolerated, dose dependent adverse effects can occur. The most common adverse effects include [headache](/source/headache), [flushing](/source/Flushing_(physiology)), [nasopharyngitis](/source/nasopharyngitis), [nasal congestion](/source/nasal_congestion), and [back pain](/source/back_pain). While it is also uncommon, there is a potential for visual disturbances to occur in patients, as well as hearing impairment.{{cite journal | vauthors = Zhang X, Xia L, Yang Q, Tang P | title=Phosphodiesterase type 5 inhibitors related hearing impairment: a real world study based on the FDA adverse event reporting system | journal=Scientific Reports | volume=14 | date=April 2024 | issn=2045-2322 | pmid=38679603 | pmc=11056362 | doi=10.1038/s41598-024-60493-w | url=https://www.nature.com/articles/s41598-024-60493-w | access-date=2025-12-08 | page=}} == Mechanism of action == Avanafil [inhibits phosphodiesterase-5](/source/PDE5_inhibitor), preventing the degradation of cGMP.{{cite journal | vauthors = Kotera J, Mochida H, Inoue H, Noto T, Fujishige K, Sasaki T, Kobayashi T, Kojima K, Yee S, Yamada Y, Kikkawa K, Omori K | display-authors = 6 | title = Avanafil, a potent and highly selective phosphodiesterase-5 inhibitor for erectile dysfunction | journal = The Journal of Urology | volume = 188 | issue = 2 | pages = 668–674 | date = August 2012 | pmid = 22704456 | doi = 10.1016/j.juro.2012.03.115 }}{{cite journal | vauthors = Sanford M | title = Avanafil: A Review of Its Use in Patients with Erectile Dysfunction | journal = Drugs & Aging | volume = 30 | issue = 10 | pages = 853–62 | date = October 2013 | pmid = 23955441 | doi = 10.1007/s40266-013-0112-x | s2cid = 23558269 }} The increased levels of cGMP causes [vasodilation](/source/vasodilation), resulting in an increased blood flow in the penis. Avanafil's mechanism of action takes place once [nitric oxide](/source/nitric_oxide) is released, in association with sexual stimulation. ==Synthesis== Avanafil can be synthesized from a benzylamine derivative and a pyrimidine derivative:{{cite patent | country = US | number = 6797709 | inventor = Yamada K, Matsuki K, Omori K Kikkawa K | title = Aromatic nitrogen-containing 6-membered cyclic compounds | gdate = 11 December 2003 | assign1 = Tanabe Seiyaku Co }} :500px == References == {{Reflist}} == External links == * {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/avanafil | archive-url = https://web.archive.org/web/20170123205947/https://druginfo.nlm.nih.gov/drugportal/name/Avanafil | url-status = dead | archive-date = January 23, 2017 | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Avanafil }} {{Drugs for erectile dysfunction and PE}} {{Phosphodiesterase inhibitors}} {{Portal bar | Medicine}} Category:Hydroxymethyl compounds Category:Carboxamides Category:Chlorobenzene derivatives Category:PDE5 inhibitors Category:Phenol ethers Category:Aminopyrimidines Category:Pyrrolidines Category:Erectile dysfunction drugs Category:Enones --- Adapted from the Wikipedia article [Avanafil](https://en.wikipedia.org/wiki/Avanafil) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Avanafil?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.