Avanafil

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Avanafil
Avanafil.svg
Avanafil ball-and-stick.png
Avanafil is a PDE5 inhibitor
Clinical data
Trade namesStendra
License data
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration
Oral
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC23H26ClN7O3
Molar mass483.951 g/mol
3D model (JSmol)
 ‹See TfM›☒N☑Y (what is this?)  (verify)

Avanafil is a PDE5 inhibitor approved for erectile dysfunction by the FDA on April 27, 2012 [1] and by EMA on June 21, 2013.[2] Avanafil is known by the trademark names Stendra and Spedra. It was invented at Mitsubishi Tanabe Pharma, formerly known as Tanabe Seiyaku Co.[3] It was then out-licensed to, and developed by, Vivus Inc. In July 2013 Vivus announced partnership with Menarini Group, which will commercialise and promote Spedra in over 40 European countries plus Australia and New Zealand.[4] On Oct. 3, 2016 Vivus announced it had sold the exclusive rights to Avanafil in USA to Metuchen Pharmaceuticals LLC of New Jersey for an upfront payment of US$70,000,000.[5]

Avanafil acts by inhibiting a specific phosphodiesterase type 5 enzyme which is found in various body tissues, but primarily in the corpus cavernosum penis, as well as the retina.[6] Other similar drugs are sildenafil, tadalafil and vardenafil. The advantage of avanafil is that it has very fast onset of action compared with other PDE5 inhibitors. It is absorbed quickly, reaching a maximum concentration in about 30–45 minutes.[7] About two-thirds of the participants were able to engage in sexual activity within 15 minutes.[7]

Synthesis[edit]

Avanafil can be synthesized from a benzylamine derivative and a pyrimidine derivative:[8]

Avanafil synthesis.png

See also[edit]

References[edit]

  1. ^ "FDA approves Stendra for erectile dysfunction" (Press release). Food and Drug Administration (FDA). April 27, 2012.
  2. ^ "Spedra (avanafil)". European Medicines Agency. Retrieved 17 April 2014.
  3. ^ https://patents.google.com/patent/US6656935B2
  4. ^ "Archived copy". Archived from the original on 2015-12-08. Retrieved 2013-07-26.
  5. ^ http://ir.vivus.com/news-releases/news-release-details/vivus-and-metuchen-pharmaceuticals-announce-license-agreement
  6. ^ "avanafil, Spedra". Medicine Net. Retrieved 17 April 2014.
  7. ^ a b Kyle, Jeffery; Brown, Dana (2013). "Avanafil for Erectile Dysfunction" (PDF). Annals of Pharmacotherapy. Sage Publishing. doi:10.1177/1060028013501989. Retrieved 28 September 2013.
  8. ^ Yamada, K.; Matsuki, K.; Omori, K.; Kikkawa, K.; 2004, U.S. Patent 6,797,709

External links[edit]