N-Desmethyl Sildenafil

Names

[ Name ]:
N-Desmethyl Sildenafil

[Synonym ]:
5-(2-ethoxy-5-piperazin-1-ylsulfonylphenyl)-1-methyl-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-7-one

Biological Activity

[Description]:

N-Desmethyl Sildenafil (Desmethylsildenafil) is a major metabolite of Sildenafil. Sildenafil is a potent phosphodiesterase type 5 (PDE5) inhibitor[1][2].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

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

[In Vitro]

N-Desmethyl Sildenafil increases the amplitude of electroretinogram (ERG) recorded from the dark-adapted isolated rat retina, most probably through the enhancement of the photoreceptor cell response[1]. The formation of N-Desmethyl Sildenafil is examined using CYP3A supersomes co-expressing human P450 oxidoreductase and cytochrome b5. N-Desmethyl Sildenafil is catalyzed by CYP3A4, CYP3A5, and to a lesser extent by CYP3A7[2].

[References]

[1]. Péter Barabás, et al. Sildenafil, N-desmethyl-sildenafil and Zaprinast enhance photoreceptor response in the isolated rat retina. Neurochem Int. 2003 Nov;43(6):591-5.

[2]. Rikako Takahiro, et al. Contribution of CYP3A isoforms to dealkylation of PDE5 inhibitors: a comparison between sildenafil N-demethylation and tadalafil demethylenation. Biol Pharm Bull. 2015;38(1):58-65.

Chemical & Physical Properties

[ Density]:
1.44g/cm3

[ Boiling Point ]:
685.7ºC at 760 mmHg

[ Melting Point ]:
158-160ºC

[ Molecular Formula ]:
C₂₁H₂₈N₆O₄S

[ Molecular Weight ]:
460.55

[ Flash Point ]:
368.5ºC

[ Exact Mass ]:
460.18900

[ PSA ]:
130.59000

[ LogP ]:
2.61620

[ Vapour Pressure ]:
1.17E-18mmHg at 25°C

[ Index of Refraction ]:
1.683

Related Compounds

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