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
ChemSpider
5293660
Wikipedia
Vardenafil
Predicted Properties
PropertyValueSource
Water Solubility0.325 mg/mLALOGPS
logP2.18ALOGPS
logP1.33Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.01Chemaxon
pKa (Strongest Basic)6.21Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area109.13 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity142.71 m3·mol-1Chemaxon
Polarizability52.37 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon