Avanafil

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Avanafil
Avanafil.svg
Avanafil ball-and-stick.png
Systematic (IUPAC) name
(S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
Clinical data
Trade names Stendra
Licence data US FDA:link
Pregnancy cat. C (US)
Legal status -only (US)
Routes Oral
Identifiers
CAS number 330784-47-9 YesY
ATC code None
PubChem CID 9869929
ChemSpider 8045620 YesY
UNII DR5S136IVO YesY
KEGG D03217 YesY
ChEMBL CHEMBL1963681 N
Chemical data
Formula C23H26ClN7O3 
Mol. mass 483.951 g/mol
 N (what is this?)  (verify)

Avanafil is a PDE5 inhibitor approved for erectile dysfunction by FDA on April 27, 2012 [1] and by EMA on June 21, 2013.[2] Avanafil is known by the trademark names Stendra and Spedra and was 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.[3] 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.[4] 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.[5] It is absorbed quickly, reaching a maximum concentration in about 30–45 minutes.[6] About two-thirds of the participants were able to engage in sexual activity within 15 minutes.[6]

Synthesis[edit]

Avanafil can be synthesized from a benzylamine derivative and a pyrimidine derivative:[7]

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. ^ http://ir.vivus.com/releasedetail.cfm?releaseid=775706
  4. ^ "avanafil, Spedra". Medicine Net. Retrieved 17 April 2014. 
  5. ^ "Spedra". HealthExpress. Retrieved 17 April 2014. 
  6. ^ a b Kyle, Jeffery; Brown, Dana (2013). "Avanafil for Erectile Dysfunction". Annals of Pharmacotherapy (Sage Publishing). doi:10.1177/1060028013501989. Retrieved 28 September 2013. 
  7. ^ Yamada, K.; Matsuki, K.; Omori, K.; Kikkawa, K.; 2004, U.S. Patent 6,797,709

External links[edit]