1.0 2011-09-21 00:32:19 UTC 2015-07-21 06:57:47 UTC FDB023606 Sildenafil Sildenafil is a drug used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH), developed by the pharmaceutical company Pfizer. It was initially studied for use in hypertension (high blood pressure) and angina pectoris (a form of ischaemic cardiovascular disease). Phase I clinical trials under the direction of Ian Osterloh suggested that the drug had little effect on angina, but that it could induce marked penile erections; Sildenafil is a potent and selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum. The molecular structure of sildenafil is similar to that of cGMP and acts as a competitive binding agent of PDE5 in the corpus cavernosum, resulting in more cGMP and better erections. Without sexual stimulation, and therefore lack of activation of the NO/cGMP system, sildenafil should not cause an erection. Other drugs that operate by the same mechanism include tadalafil (Cialis) and vardenafil (Levitra); Sildenafil citrate, sold under the names Viagra, Revatio and generically under various other names, is a drug used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH), developed by the pharmaceutical company Pfizer. Viagra pills are blue and diamond-shaped with the words 'Pfizer' on one side, and 'VGR xx' (where xx stands for '25', '50' or '100', the dose of that pill in milligrams) on the other. Its primary competitors on the market are tadalafil (Cialis), and vardenafil (Levitra). [HMDB] 1-((3-(4,7-dihydro-1-Methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine 1-((3-(4,7-dihydro-1-Methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulphonyl)-4-methylpiperazine Caverta Revatio Sildenafil citrate Viagra C22H30N6O4S 474.576 474.204924168 5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one revatio 139755-83-2 CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1 InChI=1S/C22H30N6O4S/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/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29) BNRNXUUZRGQAQC-UHFFFAOYSA-N belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. Benzenesulfonamides Organic compounds Benzenoids Benzene and substituted derivatives Benzenesulfonamides Aromatic heteropolycyclic compounds Alkyl aryl ethers Azacyclic compounds Benzenesulfonyl compounds Heteroaromatic compounds Hydrocarbon derivatives Lactams N-methylpiperazines Organic oxides Organopnictogen compounds Organosulfonamides Phenol ethers Phenoxy compounds Pyrazoles Pyrazolopyrimidines Pyrimidones Sulfonyls Trialkylamines 1,4-diazinane Alkyl aryl ether Amine Aromatic heteropolycyclic compound Azacycle Azole Benzenesulfonamide Benzenesulfonyl group Ether Heteroaromatic compound Hydrocarbon derivative Lactam N-alkylpiperazine N-methylpiperazine Organic nitrogen compound Organic oxide Organic oxygen compound Organic sulfonic acid or derivatives Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfonic acid amide Organosulfonic acid or derivatives Organosulfur compound Phenol ether Phenoxy compound Piperazine Pyrazole Pyrazolopyrimidine Pyrimidine Pyrimidone Sulfonyl Tertiary aliphatic amine Tertiary amine piperazines pyrazolopyrimidine sulfonamide Solid logp 2.35 ALOGPS logs -3.04 ALOGPS solubility 4.33e-01 g/l ALOGPS logp 1.65 ChemAxon pka_strongest_acidic 7.27 ChemAxon pka_strongest_basic 5.97 ChemAxon iupac 5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one ChemAxon average_mass 474.576 ChemAxon mono_mass 474.204924168 ChemAxon smiles CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1 ChemAxon formula C22H30N6O4S ChemAxon inchi InChI=1S/C22H30N6O4S/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/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29) ChemAxon inchikey BNRNXUUZRGQAQC-UHFFFAOYSA-N ChemAxon polar_surface_area 109.13 ChemAxon refractivity 139.44 ChemAxon polarizability 51.18 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 8 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 15027 Specdb::CMs 158114 Specdb::MsMs 8471 Specdb::MsMs 8472 Specdb::MsMs 8473 Specdb::MsMs 15143 Specdb::MsMs 15144 Specdb::MsMs 15145 Specdb::MsMs 374792 Specdb::MsMs 374793 Specdb::MsMs 451475 Specdb::MsMs 451476 Specdb::MsMs 2748559 Specdb::MsMs 2748560 Specdb::MsMs 2748561 Specdb::MsMs 2934315 Specdb::MsMs 2934316 Specdb::MsMs 2934317 HMDB05039 VIA #<Reference:0x000055ce331a5110> #<Reference:0x000055ce331a4f58> #<Reference:0x000055ce331a4da0> #<Reference:0x000055ce331a4be8> #<Reference:0x000055ce331a4a30> #<Reference:0x000055ce331a4878>