Avanafil

Avanafil

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
License data	US FDA: Avanafil
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Oral
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Identifiers
CAS Number	330784-47-9
ATC code	G04BE10 (WHO)
PubChem	CID 9869929
IUPHAR/BPS	7448
ChemSpider	8045620
UNII	DR5S136IVO
KEGG	D03217
ChEMBL	CHEMBL1963681
Chemical data
Formula	C23H26ClN7O3
Molar mass	483.951 g/mol
SMILES Clc1c(OC)ccc(c1)CNc3nc(ncc3C(=O)NCc2ncccn2)N4[C@@H](CCC4)CO
InChI 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 Key:WEAJZXNPAWBCOA-INIZCTEOSA-N
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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

• Tadalafil (Cialis)
• Vardenafil (Levitra/Staxyn)
• Sildenafil (Viagra)

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. 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

External links

• Faster-Working Erectile Dysfunction Drug?. CBS News. November 24, 2009.
• Vivus says men taking avanafil were more likely to be ready for sex within 15 minutes. The Gaea Times. January 11, 2010.
• "Avanafil is the New Player in The Erectile Dysfunction Field". June 28, 2011.