Sildenafil citrateProduct ingredient for Sildenafil
- Name
- Sildenafil citrate
- Drug Entry
- Sildenafil
In eliciting its mechanism of action, sildenafil ultimately prevents or minimizes the breakdown of cyclic guanosine monophosphate (cGMP) by inhibiting cGMP specific phosphodiesterase type 5 (PDE5) 11,12,13,14,15,16,8,9. The result of doing so allows cGMP present in both the penis and pulmonary vasculature to elicit smooth muscle relaxation and vasodilation that subsequently facilitates relief in pulmonary arterial hypertension and the increased flow of blood into the spongy erectile tissue of the penis that consequently allows it to grow in size and become erect and rigid 11,12,13,14,15,16,8,9.
Interestingly enough, it is precisely via this mechanism why sildenafil was at first researched as a potential treatment for angina - or chest pain associated with inadequate blood flow to the heart - before being serendipitously indicated for treating erectile dysfunction in the late 1980s 7. Nevertheless, it is because of this mechanism that sildenafil is also indicated for treating pulmonary arterial hypertension but is also additionally notorious for interacting with various anti-anginal or anti-hypertensive agents to develop potentially rapid, excessive, and/or fatal hypotensive crises 4,5,6.
Regardless, sildenafil, among a variety of other similar or related PDE5 inhibitors, has become a common and effective treatment for erectile dysfunction and since its formal approval for medical use in the public in 1998 7, continues to see millions of prescriptions written for it internationally. Although the medication has historically been most popularly recognized as Pfizer's brand name Viagra, sildenafil is currently available generically and even as a non-prescription over the counter medication in some countries 10.
- Accession Number
- DBSALT000347
- Structure
- Synonyms
- Sildenafil citrate
- External IDs
- UK-92,480-10 / UK-92480-10
- UNII
- BW9B0ZE037
- CAS Number
- 171599-83-0
- Weight
- Average: 666.7
Monoisotopic: 666.231926778 - Chemical Formula
- C28H38N6O11S
- InChI Key
- DEIYFTQMQPDXOT-UHFFFAOYSA-N
- InChI
- InChI=1S/C22H30N6O4S.C6H8O7/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28;7-3(8)1-6(13,5(11)12)2-4(9)10/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
- IUPAC Name
- 2-hydroxypropane-1,2,3-tricarboxylic acid; 5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one
- SMILES
- OC(=O)CC(O)(CC(O)=O)C(O)=O.CCCC1=NN(C)C2=C1N=C(NC2=O)C1=CC(=CC=C1OCC)S(=O)(=O)N1CCN(C)CC1
- External Links
- KEGG Drug
- D02229
- PubChem Compound
- 62853
- ChemSpider
- 56586
- BindingDB
- 50238854
- ChEBI
- 58987
- ChEMBL
- CHEMBL1737
- Wikipedia
- Sildenafil
- Predicted Properties
Property Value Source Water Solubility 0.46 mg/mL ALOGPS logP 1.8 ALOGPS logP 1.23 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 7.63 Chemaxon pKa (Strongest Basic) 5.98 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 109.13 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 139.87 m3·mol-1 Chemaxon Polarizability 51.71 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon