Chemical Property of Avanafil
Chemical Property:
- Appearance/Colour:White solid
- Melting Point:150-152 °C
- Refractive Index:1.651
- PKA:11.84±0.46(Predicted)
- PSA：125.39000
- Density:1.373 g/cm3
- LogP:2.96070
- Storage Temp.:Refrigerator
- Solubility.:DMSO (Slightly), Methanol (Slightly, Heated)
- XLogP3:2.6
- Hydrogen Bond Donor Count:3
- Hydrogen Bond Acceptor Count:9
- Rotatable Bond Count:9
- Exact Mass:483.1785654
- Heavy Atom Count:34
- Complexity:642
- Purity/Quality:
-
99%, *data from raw suppliers
Avanafil *data from reagent suppliers
Safty Information:
- Pictogram(s):
- Hazard Codes:
- MSDS Files:
-
SDS file from LookChem
Useful:
- Drug Classes:PDE5 Inhibitors
- 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
- Recent ClinicalTrials:Daily Avanafil for Erectile Dysfunction
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Description
Avanafil (Zepeed) was approved by the Korean Health Ministry for the
treatment of erectile dysfunction (ED) in August 2011. Avanafil is a
highly selective type 5 phosphodiesterase (PDE5) inhibitor.
Avanafil is reported to be the most selective PDE5
inhibitor on the market. The onset of Tmax and half-life also varies among
the marketed PDE5 inhibitors. Sildenafil has a Tmax at 1 h and a half-life of
3–5 h. Vardenafil is somewhat similar with a Tmax of 0.6 h and a half-life of
4–6 h. Tadalafil has the longest half-life among the marketed drugs with a
half-life of 17 h. Avanafil has a fast onset of action reaching Tmax in 0.6 h
with a half-life of 1.2 h. A synthesis of avanafil (TA-1790) is described
in the patent literature. The main elimination route of avanafil
is through the bile and feces. Avanafil was also found to be reabsorbed
through enterohepatic recirculation.
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Uses
Avanafil is a highly selective PDE5 inhibitor with IC50 of 1 nM. A phosphodiesterase (PDE5) inhibitor, used to treat erectile dysfunction.
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Clinical Use
Avanafil was originally discovered at Tanabe Seiyaku (now
Mitsubishi Tanabe). JW Pharmaceutical (previously Choongwae Pharma) and VIVUS have since developed and launched avanafil,
which is an oral PDE5 inhibitor for the treatment of erectile dysfunction
(ED). Although many marketed PDE5 inhibitors (e.g. sildenafil,
vardenafil and tadalafil) are available for the treatment of ED,
many patients are still unable to achieve the desired results and
experience undesired side-effects with these existing medications.
As such, second-generation PDE5 inhibitors with enhanced PDE5
selectivity, shorter systemic half-lives, and improved tolerability
are desired. Developed to meet these criteria, Avanafil exhibited
good oral bioavailability and PDE5 selectivity in both preclinical
studies and clinical trials. Avanafil had a short onset of action
(35 min) and short half-life (1.5 h).
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Drug interactions
Potentially hazardous interactions with other drugs
Alpha-blockers: enhanced hypotensive effect -
maximum dose 50 mg.
Antibacterials: concentration possibly increased
by clarithromycin and telithromycin - avoid;
concentration increased by erythromycin - reduce
avanafil dose; concentration reduced by rifampicin -
avoid.
Antifungals: concentration increased by ketoconazole
- avoid and fluconazole - reduce avanafil dose;
concentration possibly increased by itraconazole and
voriconazole - avoid.
Antivirals: concentration possibly increased by
atazanavir, indinavir and saquinavir - avoid;
concentration possibly reduced by efavirenz - avoid;
concentration possibly increased by fosamprenavir
- reduce avanafil dose; concentration significantly
increased by ritonavir - avoid.
Aprepitant: concentration possibly increased by
aprepitant - reduce avanafil dose.
Calcium channel blockers: concentration possibly
increased by diltiazem and verapamil - reduce
avanafil dose.
Cobicistat: concentration of avanafil possibly
increased - avoid.
Nicorandil: possibly enhanced hypotensive effect -
avoid.
Nitrates: enhanced hypotensive effect - avoid.
Riociguat: possibly enhanced hypotensive effect -
avoid.
