Vardenafil hydrochlorideProduct ingredient for Vardenafil
- Name
- Vardenafil hydrochloride
- Drug Entry
- Vardenafil
Vardenafil is a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5) and an oral therapy for the treatment of erectile dysfunction.5,6 During sexual stimulation, nitric oxide (NO) is released from nerve endings and endothelial cells in the corpus cavernosum, activating the enzyme guanylate cyclase and increasing the synthesis of cGMP in the smooth muscle cells of the corpus cavernosum. PDE5 inhibitors, such as vardenafil, inhibit the degradation of cGMP and allow increased blood flow into the penis, resulting in an erection.1,5,6. Compared to sildenafil and tadalafil, vardenafil is a more potent inhibitor of PDE5; however, its selectivity for other PDE isoforms is lower than the one detected for tadalafil.4
The FDA approved the use of vardenafil for the treatment of erectile dysfunction in 2003. Although other PDE5 inhibitors such as sildenafil and tadalafil have been associated with rare cases of acute liver injury, the use of vardenafil has not been linked to hepatotoxic effects.3 The use of vardenafil as a monotherapy for the treatment of pulmonary arterial hypertension has also been evaluated.2
- Accession Number
- DBSALT001741 (DBSALT000933)
- Structure
- Synonyms
- Vardenafil HCl / Vardenafil hydrochloride hydrate / Vardenafil hydrochloride trihydrate / Vardenafil hydrochloride trydrate
- External IDs
- BAY 38-9456 / BAY-38-9456
- UNII
- 5M8S2CU0TS
- CAS Number
- 330808-88-3
- Weight
- Average: 579.11
Monoisotopic: 578.2289465 - Chemical Formula
- C23H39ClN6O7S
- InChI Key
- FBCDRHDULQYRTB-UHFFFAOYSA-N
- InChI
- InChI=1S/C23H32N6O4S.ClH.3H2O/c1-5-8-20-24-16(4)21-23(30)25-22(26-29(20)21)18-15-17(9-10-19(18)33-7-3)34(31,32)28-13-11-27(6-2)12-14-28;;;;/h9-10,15H,5-8,11-14H2,1-4H3,(H,25,26,30);1H;3*1H2
- IUPAC Name
- 2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propyl-1H,4H-imidazo[4,3-f][1,2,4]triazin-4-one trihydrate hydrochloride
- SMILES
- O.O.O.Cl.CCCC1=NC(C)=C2N1NC(=NC2=O)C1=CC(=CC=C1OCC)S(=O)(=O)N1CCN(CC)CC1
- External Links
- ChemSpider
- 5293660
- Wikipedia
- Vardenafil
- Predicted Properties
Property Value Source Water Solubility 0.325 mg/mL ALOGPS logP 2.18 ALOGPS logP 1.33 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 8.01 Chemaxon pKa (Strongest Basic) 6.21 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 109.13 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 142.71 m3·mol-1 Chemaxon Polarizability 52.37 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon