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Avanafil

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Avanafil
Clinical data
Trade namesStendra
License data
Routes of
administration		Oral
ATC code
Legal status
Legal status
Identifiers
  • (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H26ClN7O3
Molar mass483.951 g/mol g·mol−1
3D model (JSmol)
  • Clc1c(OC)ccc(c1)CNc3nc(ncc3C(=O)NCc2ncccn2)N4[C@@H](CCC4)CO
  • InChI=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 checkY
  • Key:WEAJZXNPAWBCOA-INIZCTEOSA-N checkY
 ☒NcheckY (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 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. It is absorbed quickly, reaching a maximum concentration in about 30–45 minutes.[5] About two-thirds of the participants were able to engage in sexual activity within 15 minutes.[5]

Synthesis

Avanafil can be synthesized from a benzylamine derivative and a pyrimidine derivative:[6]

See also

References

  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. ^ 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.
  6. ^ Yamada, K.; Matsuki, K.; Omori, K.; Kikkawa, K.; 2004, U.S. patent 6,797,709
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