Correlation Engine 2.0
Clear Search sequence regions
Bookmark Forward

QuickView for Sildenafil (compound)

Name: sildenafil
PubChem Compound ID: 5212
Molecular formula: C22H30N6O4S
Molecular weight: 474.578 g/mol
KBio2_007171; 171599-83-0; 1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine; KBio3_002927; Spectrum2_001648; DivK1c_006894; KBio1_001838; BAS 04213629; Spectrum3_001892; VIA.
show more »
Name: sildenafil
Name (isomeric): DB00203
Drug Type: small molecule
Sildenafil Citrate
Brand: Revatio, Viagra
Category: Vasodilator Agents, Phosphodiesterase Inhibitors
CAS number: 139755-83-2
Indication: For the treatment of erectile dysfunction and to relieve symptoms of pulmonary arterial hypertension (PAH).
Erections are controlled by the parasympathetic nervous system. Upon sexual stimulation, a decrease in vascular resistance is mediated by acetylcholine and nitric oxide resulting in vasodilation. The hemodynamic mechanism of an erection is comprised of five stages. During the latent stage, arterial and carvernous smooth muscle relaxation occurs. Va...
show more »
Mechanism of Action:
Sildenafil inhibits the cGMP-specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum located around the penis. Penile erection during sexual stimulation is caused by increased penile blood flow resulting from the relaxation of penile arteries and corpus cavernosal smooth muscle. This response i...
show more »
Absorption: >90% absorbed with ~40% reaching systemic circulation unchanged following first-pass metabolism
Protein binding: 96%
Biotransformation: Sildenafil appears to be completely metabolized in the liver to 16 metabolites. Its metabolism is mediated mainly by cytochrome P450 microsomal isozymes 3A4 (major route) and 2C9 (minor route). The major circulating metabolite, N-demethylated metabolite, has PDE selectivity similar to the parent drug and ~50% of its in vitro potency. The N-demethylated metabolite is further metabolized to an N-dealkylated N,N-de-ethylated metabolite. Sildenafil also undergoes N-dealkylation followed by N-demethylation of the piperazine ring.
Route of elimination: Sildenafil is cleared predominantly by the CYP3A (major route) and cytochrome P450 2C9 (CYP2C9, minor route) hepatic microsomal isoenzymes. After either oral or intravenous administration, sildenafil is excreted as metabolites predominantly in the feces (approximately 80% of the administered oral dose) and to a lesser extent in the urine (approximately 13% of the administered oral dose).
Half Life: 4 hours
Affected organisms: Humans and other mammals
Drug interaction:
CiprofloxacinCiprofloxacin may increase the serum level of sildenafil.
IndinavirThe protease inhibitor, indinavir, may increase the effect and toxicity of sildenafil.
VoriconazoleVoriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of sildenafil by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of sildenafil if voriconazole is initiated, discontinued or dose changed.
AmprenavirThe protease inhibitor, amprenavir, may increase the effect and toxicity of sildenafil.
TelithromycinTelithromycin may reduce clearance of Sildenafil. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Sildenafil if Telithromycin is initiated, discontinued or dose changed.
show more »