2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propyl-3H,4H-imidazo[4,3-f][1,2,4]triazin-4-one

• ChemBase ID: 73057
• Molecular Formular: C23H32N6O4S
• Molecular Mass: 488.60298
• Monoisotopic Mass: 488.22057453
• SMILES: C1N(CCN(C1)S(=O)(=O)c1ccc(c(c1)c1nn2c(c(=O)[nH]1)c(nc2CCC)C)OCC)CC
• Canonical SMILES: CCOc1ccc(cc1c1[nH]c(=O)c2n(n1)c(CCC)nc2C)S(=O)(=O)N1CCN(CC1)CC
• InChI: InChI=1S/C23H32N6O4S/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)
• InChIKey: SECKRCOLJRRGGV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propyl-3H,4H-imidazo[4,3-f][1,2,4]triazin-4-one
• IUPAC Traditional name: @vardenafil
• Synonyms: Vivanza; Vardenafil

Database IDs

• CAS Number: 224785-90-4
• PubChem SID: 162037977
• PubChem CID: 110634

CALCULATED PROPERTIES

• Acid pKa: 8.996414
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.3222461
• LogD (pH = 7.4): 1.0718623
• Log P: 1.1085637
• Molar Refractivity: 132.2948 cm^3
• Polarizability: 50.140568 Å^3
• Polar Surface Area: 109.13 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2515

Research Area: Cardiovascular Disease
Biological Activity:
Vardenafil Hydrochloride Trihydrate (Vivanza) is a new type PDE inhibitor with IC50 of 0.7 and 180 nM for PDE5 and PDE1, respectively. Vardenafil’s indications and contra-indications are the same as with other PDE5 inhibitors; it is closely related in function to sildenafil citrate (Viagra) and tadalafil (Cialis). Structurally, the difference between the vardenafil molecule and sildenafil citrate is a nitrogen atom’s position and the change of sildenafil’s piperazine ring methyl group to an ethyl group. [1] Chronic vardenafil treatment improves erectile function via structural maintenance of penile corpora cavernosa in rats with acute arteriogenic erectile dysfunction. [2]

REFERENCES

• Kamenov ZA. J Sex Med. 2010 Dec 8.