Vardenafil

Names

[ Name ]:
Vardenafil

[Synonym ]:
Vardenafil (INN)
Vivanza
2-{2-Ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one
4-[2-ethoxy-5-(4-ethyl-piperazine-1-sulfonyl)-phenyl]-9-methyl-7-propyl-3,5,6,8-tetrazabicyclo[4.3.0]nona-3,7,9-trien-2-one
Vardenafil hydrochloride trihydrate
[14C]-Vardenafil
2-{2-Ethoxy-5-[(4-ethyl-1-piperazinyl)sulfonyl]phenyl}-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one
2-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylphenyl]-5-methyl-7-propyl-1H-imidazo[5,1-f][1,2,4]triazin-4-one
Vardenafil HCl Trihydrate
4-[2-eyhoxy-5-(4-ethylpiperazin-1-yl)sulfonyl-phenyl]-9-methyl-7-propyl-3,5,6,8-tetrazabicyclo[4,3,0] none 3,7,9 trien-2-one
Imidazo[5,1-f][1,2,4]triazin-4(3H)-one, 2-[2-ethoxy-5-[(4-ethyl-1-piperazinyl)sulfonyl]phenyl]-5-methyl-7-propyl-
vardenafil
Levitra (TN)

Biological Activity

[Description]:

Vardenafil is a PDE5 inhibitor used for treating erectile dysfunction.Target: PDE5Vardenafil specifically inhibited the hydrolysis of cGMP by PDE5 with an IC50 of 0.7 nM (6.6 nM). In contrast, the IC50 of vardenafil for PDE1 was 180 nM; for PDE6, 11 nM; for PDE2, PDE3 and PDE4, more than 1000 nM. Relative to PDE5, the ratios of the IC50 for PDE1 were 257 (60), for PDE6 16 (7.4). Vardenafil significantly enhanced the SNP-induced relaxation of human trabecular smooth muscle at 3 nM (10 nM). Vardenafil also significantly potentiated both ACh-induced and transmural electrical stimulation-induced relaxation of trabecular smooth muscle [1]. Both vardenafil doses(10 mg or 20 mg) significantly enhanced the rates of successful penetration (P < 0.0001) and successful intercourse (P < 0.0001) compared with placebo. Vardenafil treatment was effective in increasing intercourse success rates at all levels of baseline ED severity, at each level of plasma HbA1c, and for type 1 and 2 diabetes [2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE)

Research Areas >> Endocrinology

[References]

[1]. Saenz de Tejada, I., et al., The phosphodiesterase inhibitory selectivity and the in vitro and in vivo potency of the new PDE5 inhibitor vardenafil. Int J Impot Res, 2001. 13(5): p. 282-90.

[2]. Goldstein, I., et al., Vardenafil, a new phosphodiesterase type 5 inhibitor, in the treatment of erectile dysfunction in men with diabetes: a multicenter double-blind placebo-controlled fixed-dose study. Diabetes Care, 2003. 26(3): p. 777-83.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
692.2ºC at 760mmHg

[ Melting Point ]:
214-216ºC

[ Molecular Formula ]:
C₂₃H₃₂N₆O₄S

[ Molecular Weight ]:
488.60

[ Flash Point ]:
372.5ºC

[ PSA ]:
121.28000

[ LogP ]:
2.65

[ Vapour Pressure ]:
5.17E-19mmHg at 25°C

[ Index of Refraction ]:
1.656

[ Storage condition ]:
?20°C

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H302 + H312 + H332-H319

[ Precautionary Statements ]:
P210-P261-P302 + P352 + P312-P304 + P340 + P312-P337 + P313-P403 + P235

[ Hazard Codes ]:
F,Xn

[ Risk Phrases ]:
11-20/21/22-36

[ Safety Phrases ]:
16-36/37

[ RIDADR ]:
UN1230 - class 3 - PG 2 - Methanol, solution

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Improvement of exercise capacity in monocrotaline-induced pulmonary hypertension by the phosphodiesterase-5 inhibitor Vardenafil.

Respir. Physiol. Neurobiol. 186(1) , 61-4, (2013)

Vardenafil, a phosphodiesterase-5 inhibitor, is approved for the therapy of erectile dysfunction. However, in contrast to Sildenafil and Tadalafil, little is known about its effects on pulmonary hyper...

SOP conservative (medical and mechanical) treatment of erectile dysfunction.

J. Sex. Med. 10(1) , 130-71, (2013)

Erectile dysfunction (ED) is the most frequently treated male sexual dysfunction worldwide. ED is a chronic condition that exerts a negative impact on male self-esteem and nearly all life domains incl...

High inter-individual variability of vardenafil pharmacokinetics in patients with pulmonary hypertension.

Eur. J. Clin. Pharmacol. 69(2) , 197-207, (2013)

To evaluate the pharmacokinetic parameters of a single oral dose of vardenafil in patients with pulmonary hypertension (PH).Sixteen patients with PH received vardenafil in single oral doses (20, 10 or...