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
Thumb
Synonyms
Not Available
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=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1
External Links
KEGG Drug
D02229
PubChem Compound
62853
ChemSpider
56586
ChEBI
58987
ChEMBL
CHEMBL1737
Wikipedia
Sildenafil
Predicted Properties
PropertyValueSource
Water Solubility0.46 mg/mLALOGPS
logP1.8ALOGPS
logP1.35ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)10.92ChemAxon
pKa (Strongest Basic)5.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area109.13 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity139.87 m3·mol-1ChemAxon
Polarizability49.74 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon