Sildenafil

Base Information Edit

Chemical Name:Sildenafil
CAS No.:139755-83-2
Molecular Formula:C22H30N6O4S
Molecular Weight:474.584
Hs Code.:38220090
Mol file:139755-83-2.mol

Synonyms:4-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonyl-phenyl]-9-methyl-7-propyl-3,5,8,9-tetrazabicyclo[4.3.0]nona-3,7,10-trien-2-one;Piperazine,1-[[3-(4,7-dihydro-1-methyl-7- oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin- 5-yl)-4-ethoxyphenyl]sulfonyl]-4-methyl-;Serum Albumin Iodine;Sildenafil Mesylate;Hongdenafil (Acetildenafil);

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Chemical Property of Sildenafil Edit

Chemical Property:

Appearance/Colour:White crystalline powder
Vapor Pressure:6.1E-18mmHg at 25°C
Melting Point:187-189 ºC
Refractive Index:1.664
Boiling Point:672.4 ºC at 760 mmHg
PKA:pKa 8.7 (Uncertain)
Flash Point:360.5 ºC
PSA：121.80000
Density:1.39 g/cm³
LogP:2.56750
Storage Temp.:Refrigerator
Solubility.:DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

Safty Information:

Pictogram(s): Xi,T,F
Hazard Codes:Xi,T,F
Statements: 36/37/38-39/23/24/25-23/24/25-11
Safety Statements: 22-24/25-36-26-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Uses Sildenafil, the first US FDA-approved, oral phosphodiesterase type-5 inhibitor, has revolutionized the treatment of erectile dysfunction sine its approval in 1998. Since sildenafil is a potent inhibitor of cyclic guanosine monophosphate in the corpus cavernosum and therefore increases the penile response to sexual stimulation. Sildenafil is a phosphodiesterase-5 (PDE5) inhibitor. It is indicated for the treatment of erectile dysfunction (ED). Sildenafil is an orally active selective type 5 cGMP phosphodiesterase inhibitor.
Indications Sildenafil Citrate is an oral drug used to treat male erectile dysfunction and is a 5-phosphodiesterase inhibitor developed by the American Pfizer Pharmaceuticals to originally treat cardiovascular disease that was later discovered to improve patients'sex lives. Sildenafil Citrate treats erectile dysfunction and was the first clinical oral drug used to specifically target male erectile dysfunction. Sildenafil (Viagra) is a selective inhibitor of PD-5, an enzyme that inactivates cGMP. Vardenifil (Levitra) is a particularly effective inhibitor of PD-5. It has a shorter onset of action and can be used in smaller doses than sildenafil. Other drugs used in the treatment of ED exert their effects through other biochemical pathways, both central and peripheral.
Description Sildenafil was launched as Viagra in the US for the treatment of organic orland psychological male erectile dysfunction (ED). It is an orally bioavailable pyrazolopyrimidinone derivative structurally related to zaprinast, with vasodilating and potential anti-inflammatory activities. Upon oral administration, sildenafil selectively targets and inhibits cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5), thereby inhibiting the PDE5-mediated degradation of cGMP found in smooth muscle and increasing cGMP availability. This results in prolonged smooth muscle relaxation in the corpus cavernosum of the penis, thereby causing vasodilation, blood engorgement and a prolonged penile erection.
Therapeutic Function Vasodilator
Clinical Use Sildenafil is a selective inhibitor of cGMP-specific PD-5 and therefore inhibits the degradation of cGMP. PD-5, the predominant type in the corpus cavernosum, also is present in other tissues (e.g., lungs, platelets, and eye). The selective inhibition of this enzyme facilitates the release of nitric oxide and smooth muscle relaxation of the corpus cavernosa. Sildenafil enhances erection by augmenting nitric oxide–mediated relaxation pathways. It has been suggested that sildenafil’s mechanism of action is due to cross-talk between cGMP- and cAMPdependent transduction pathways within the cavernous muscles.
Drug interactions Potentially hazardous interactions with other drugs Alpha-blockers: enhanced hypotensive effect - avoid for 4 hours after sildenafil. Antibacterials: concentration increased by clarithromycin and erythromycin - consider reducing sildenafil dose or frequency. Antifungals: concentration increased by ketoconazole - reduce initial dose for ED and avoid for PAH; concentration increased by itraconazole - reduce initial dose of sildenafil. Antivirals: ritonavir significantly increases sildenafil concentration - avoid; concentration possibly increased by saquinavir, fosamprenavir and indinavir - reduce dose of sildenafil; concentration reduced by etravirine; side effects possibly increased by atazanavir; increased risk of ventricular arrhythmias with saquinavir - avoid; avoid with telaprevir; avoid with tipranavir for PAH. Cobicistat: concentration of sildenafil possibly increased - reduce initial dose for ED and avoid for PAH. Nicorandil: enhanced hypotensive effect - avoid. Nitrates: enhanced hypotensive effect - absolutely contraindicated. Riociguat: enhanced hypotensive effect - avoid.

Technology Process of Sildenafil

There total 66 articles about Sildenafil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%