Structure via PubChem · Public domain (PubChem)
avanafil
Sign in to saveAlso known as Spedra®, Stendra®, TA-1790, (S)-4-(3-Chloro-4-methoxybenzylamino)-2-(2-hydroxymethylpyrrolidin-1-yl)-N-pyrimidin-2-ylmethyl-5-pyrimidinecarboxamide
Avanafil is a PDE5 inhibitor approved for erectile dysfunction by the FDA on April 27, 2012 and by EMA on June 21, 2013. 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., which partnered with Menarini Group to commercialise Spedra in over forty European countries, Australia, and New Zealand. Metuchen Pharmaceuticals obtained exclusive rights within the United States.
Chemical data
- Formula
- C23H26ClN7O3
- Molecular weight
- 483.9 g/mol
- IUPAC name
- 4-[(3-chloro-4-methoxyphenyl)methylamino]-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-N-(pyrimidin-2-ylmethyl)pyrimidine-5-carboxamide
- SMILES
- COC1=C(C=C(C=C1)CNC2=NC(=NC=C2C(=O)NCC3=NC=CC=N3)N4CCC[C@H]4CO)Cl
- InChIKey
- WEAJZXNPAWBCOA-INIZCTEOSA-N
- XLogP
- 2.6
- Polar surface area
- 125 Ų
- H-bond donors
- 3
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 483.178565
Show 6 more facts
- chemical formula
- C₂₃H₂₆ClN₇O₃
- canonical SMILES
- COC1=C(C=C(C=C1)CNC2=NC(=NC=C2C(=O)NCC3=NC=CC=N3)N4CCCC4CO)Cl
- isomeric SMILES
- COC1=C(C=C(C=C1)CNC2=NC(=NC=C2C(=O)NCC3=NC=CC=N3)N4CCC[C@H]4CO)Cl
- defined daily dose
- 0.1
- World Health Organisation international non-proprietary name
- avanafil
- Commons category
- Avanafil
via Wikidata · CC0
~2 min read
Article
6 sectionsContents
- Medical use
- Adverse effects
- Mechanism of action
- Synthesis
- References
- External links
Avanafil is a PDE5 inhibitor approved for erectile dysfunction by the FDA on April 27, 2012 and by EMA on June 21, 2013. 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., which partnered with Menarini Group to commercialise Spedra in over forty European countries, Australia, and New Zealand. Metuchen Pharmaceuticals obtained exclusive rights within the United States.
Avanafil acts by inhibiting a specific phosphodiesterase type 5 enzyme found in various body tissues, primarily in the corpus cavernosum penis. 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 serum concentration in about thirty to forty-five minutes. About two-thirds of the participants were able to engage in sexual activity within fifteen minutes.