Structure via PubChem · Public domain (PubChem)
آوانافیل
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
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
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2011
- Admin. routes
- oral
- Indications
- erectile dysfunction, kidney disease, Impotence
via ChEMBL · EBI
Wikidata facts
- Mass
- 483.178565
- Has use
- medication
Show 7 more facts
- significant drug interaction
- isosorbide dinitrate
- 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