{"ATC Code":["G - Genito urinary system and sex hormones","G04 - Urologicals","G04B - Urologicals","G04BE - Drugs used in erectile dysfunction","G04BE03","G04BE03 - Sildenafil","QG - Genito urinary system and sex hormones","QG04 - Urologicals","QG04B - Urologicals","QG04BE - Drugs used in erectile dysfunction","QG04BE03 - Sildenafil"],"Abbreviation":["Viagra"],"Absorption, Distribution and Excretion":"Sildenafil is known to be quickly absorbed, with maximum plasma concentrations being observed within 30-120 minutes (with a median of 60 minutes) of oral administration in a fasting patient. Moreover, the mean absolute bioavailability observed for sildenafil is about 41% (from a range of 25-63%). In particular, after oral three times a day dosing of sildenafil, the AUC and Cmax increase in proportion with dose over the recommended dosage range of 25-100 mg.  When used in pulmonary arterial hypertension patients, however, the oral bioavailability of sildenafil after a dosing regimen of 80 mg three times a day, was on average 43% greater than compared to the lower doses.  Finally, if sildenafil is administered orally with food, the rate of absorption is observed to be decreased with a mean delay in Tmax of about 60 minutes and a mean decrease in Cmax of approximately 29%. Regardless, the extent of absorption is not observed to be significantly affected as the recorded AUC decreased by only about 11 %.","Adverse Effects":"Warnings and Precautions","Aliases":["Aphrodil","Vizarsin","Sildenafilo","Patrex","Sildenafil teva","Sildenafil actavis","1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine","HIP0908","HIP-0908","CHEBI:9139","1-[[3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methylpiperazine","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-","sildenafilum","Nipatra","5-(2-ethoxy-5-(4-methylpiperazine-1-sulfonyl)phenyl)-1-methyl-3-propyl-1H,4H,7H-pyrazolo(4,3-d)pyrimidin-7-one","5-[2-ethoxy-5-(4-methylpiperazine-1-sulfonyl)phenyl]-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one","Dtxcid003579","G04BE03","C22h30n6o4s","5-(2-Ethoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one","CHEMBL192","5-[2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one","7H-Pyrazolo[4,3-d]pyrimidin-7-one, 5-[2-ethoxy-5-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]-1,6-dihydro-1-methyl-3-propyl-","Uk 92480-10","5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one","5-{2-Ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1h,6h,7h-pyrazolo[4,3-d]pyrimidin-7-one","5-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one","5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one","Smr000752512","HSDB 7305","Sr-05000001934","Ncgc00159496-02","Sildenafil#","1udt","1xos","5-(2-ethoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one","5-(2-Ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl)-1-methyl-3-propyl-1h,4h,7h-pyrazolo[4,3-d]pyrimidin-7-one","5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo(4,3-d]pyrimidin-7-one","5-[2-ethoxy-5-(4-methylpiperazinylsulfonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one","Spectrum_001555","SpecPlus_000798","Spectrum2_001648","Spectrum3_001892","Spectrum4_000586","Spectrum5_001508","Sildenafil; viagra","Cambridge id 7030299","Schembl1895","BSPBio_003424","KBioGR_001052","KBioSS_002035","Mls001240224","Mls001304737","Mls006011565","orb401930","Bidd:gt0352","DivK1c_006894","Schembl492566","Spectrum1504099","SPBio_001775","GTPL4743","Schembl5795456","Schembl8100377","Sildenafil - Bio-X trade mark","Schembl29361663","BDBM14390","KBio1_001838","KBio2_002035","KBio2_004603","KBio2_007171","KBio3_002927","MSK2278","2h42","HMS1684K08","HMS1922B19","HMS2089M12","HMS2093O17","HMS2233L22","HMS3372N07","HMS3715P17","HMS3740G19","Sildenafil 1.0 mg/ml in Methanol","AC-938","Bdbm50238854","CCG-21806","CCG-39076","EBC-13158","EBC-27192","s4684","STL565123","Akos008901403","Akos025397193","Akos037623334","CS-1577","DB00203","FD12062","FS27828","SB17345","Ncgc00095099-01","Ncgc00095099-02","Ncgc00095099-03","Ncgc00095099-04","Ncgc00095099-16","Ncgc00370976-03","5-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonyl-phenyl]-1-methyl-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-7-one","5-{2-(ethyloxy)-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one","AS-48884","BS164403","HY-15025","Smr004703325","Sbi-0051920.p002","NS00010359","UK-9248010","C07259","D08514","En300-117245","Ab00052444-02","Ab00052444-03","Ab00052444_04","Ab00052444_05","F549627","F979721","Sr-01000504734","Sr-01000504734-1","Sr-05000001934-1","Sr-05000001934-2","Brd-k50128260-001-01-6","Brd-k79759585-001-02-1","Brd-k79759585-048-01-4","Brd-k79759585-048-03-0","Brd-k79759585-048-04-8","Z1522567175","1-((3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1h-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine","5-[2-Ethoxy  -5-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]-1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one","5-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonyl-phenyl]-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one","5-[2-Ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one","5-[2-Ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-1-methyl-3-n-propyl-1.6-dihydro-7H-pyrazolo[4,3-d]Pyrimidin-7-one","5-[2-Ethoxy-5-(4-methylpiperazine-1-sulfonyl)phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one","5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7-ol","5-{2-ethoxy-5-[(4-methylpiperazine-1-)sulfonyl]phenyl}-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one","Piperazine, 1-((3-(6,7-dihydro-1-methyl-7-oxo-3-propyl-1h-pyrazolo(4,3-d)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methyl-"],"Biological Half-Life":"The terminal phase half-life observed for sildenafil is approximately 3 to 5 hours.","CAS":"139755-83-2","ChemicalClasses":["piperazine"],"Chirality":"achiral","Color/Form":"Crystals","DBI-IGS":["Sildenafil"],"DTXSID":"6023579","Dosing Info":[{"Method":"Oral","Tiers":{"Common":{"Entries":5,"Lower":35,"Percentage":71.4,"Unit":"mg","Upper":50},"Extreme":{"Entries":0,"Lower":50,"Percentage":0,"Unit":"mg","Upper":50},"Heavy":{"Entries":0,"Lower":50,"Percentage":0,"Unit":"mg","Upper":50},"Light":{"Entries":2,"Lower":35,"Percentage":28.6,"Unit":"mg","Upper":35},"Strong":{"Entries":0,"Lower":50,"Percentage":0,"Unit":"mg","Upper":50}}}],"Drug Classes":["Breast Feeding","Lactation","Milk, Human","Antihypertensive Agents","Cardiovascular Agents","Phosphodiesterase 5 Inhibitors","Urologic Agents","Vasodilator Agents"],"Drug Indication":"Sildenafil is a phosphodiesterase-5 (PDE5) inhibitor that is predominantly employed for two primary indications:  (1) the treatment of erectile dysfunction; and  (2) treatment of pulmonary hypertension, where: a) the US FDA specifically indicates sildenafil for the treatment of pulmonary arterial hypertension (PAH) (WHO Group I) in adults to improve exercise ability and delay clinical worsening. The delay in clinical worsening was demonstrated when sildenafil was added to background epoprostenol therapy. Studies establishing effectiveness were short-term (12 to 16 weeks), and included predominately patients with New York Heart Association (NYHA) Functional Class II-III symptoms and idiopathic etiology (71%) or associated with connective tissue disease (CTD) (25%);  b) the Canadian product monograph specifically indicates sildenafil for the treatment of primary pulmonary arterial hypertension (PPH) or pulmonary hypertension secondary to connective tissue disease (CTD) in adult patients with WHO functional class II or III who have not responded to conventional therapy. In addition, improvement in exercise ability and delay in clinical worsening was demonstrated in adult patients who were already stabilized on background epoprostenol therapy; and  c) the EMA product information specifically indicates sildenafil for the treatment of adult patients with pulmonary arterial hypertension classified as WHO functional class II and III, to improve exercise capacity. Efficacy has been shown in primary pulmonary hypertension and pulmonary hypertension associated with connective tissue disease. The EMA label also indicates sildenafil for the treatment of pediatric patients aged 1 year to 17 years old with pulmonary arterial hypertension. Efficacy in terms of improvement of exercise capacity or pulmonary hemodynamics has been shown in primary pulmonary hypertension and pulmonary hypertension associated with congenital heart disease.","Drug Warnings":"Administration of Viagra with nitric oxide donors such as organic nitrates or organic nitrites in any form is contraindicated. Consistent with its known effects on the nitric oxide/cGMP pathway, Viagra was shown to potentiate the hypotensive effects of nitrates.","DurationOfAction":"","EliminationHalfLife":"3 – 4 hours","Erowid Experience Reports":[],"Esters":[],"European Community (EC) Number":"604-158-7","FDA Pharmacological Classification":[{"Name":"FDA UNII","ReferenceNumber":34,"Value":{"StringWithMarkup":[{"String":"3M7OB98Y7H"}]}},{"Name":"Active Moiety","ReferenceNumber":34,"Value":{"StringWithMarkup":[{"String":"SILDENAFIL"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":34,"Value":{"StringWithMarkup":[{"String":"Established Pharmacologic Class [EPC] - Phosphodiesterase 5 Inhibitor"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":34,"Value":{"StringWithMarkup":[{"String":"Mechanisms of Action [MoA] - Phosphodiesterase 5 Inhibitors"}]}},{"Name":"FDA Pharmacology Summary","ReferenceNumber":34,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-135398744","Length":10,"Start":0,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Sildenafil"},{"Extra":"CID-135398744","Length":10,"Start":74,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/sildenafil"}],"String":"Sildenafil is a Phosphodiesterase 5 Inhibitor. The mechanism of action of sildenafil is as a Phosphodiesterase 5 Inhibitor."}]}},{"Name":"Non-Proprietary Name","ReferenceNumber":93,"Value":{"StringWithMarkup":[{"String":"SILDENAFIL"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":93,"Value":{"StringWithMarkup":[{"String":"Phosphodiesterase 5 Inhibitors [MoA]; Phosphodiesterase 5 Inhibitor [EPC]"}]}}],"Formating":[],"HMDB ID":"HMDB0005039","HeavyAtomCount":33,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Cardiovascular Agents; Phosphodiesterase 5 Inhibitors; Urologic Agents; Vasodilator Agents","IUPACName":"5-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-1-methyl-3-propyl-6H-pyrazolo[4,5-d]pyrimidin-7-one","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)","InChIKey":"BNRNXUUZRGQAQC-UHFFFAOYSA-N","Interactions":"Sildenafil and other phosphodiesterase (PDE) type 5 inhibitors (e.g., tadalafil, vardenafil) profoundly potentiate the vasodilatory effects (e.g., a systolic blood pressure reduction exceeding 25 mm Hg with sildenafil) of organic nitrates and nitrites (e.g., nitroglycerin, isosorbide dinitrate), and potentially life-threatening hypotension and/or hemodynamic compromise can result. Nitrates and nitrites promote the formation of cyclic guanosine monophosphate (cGMP) by stimulating guanylate cyclase, and PDE type 5 inhibitors (e.g., sildenafil, tadalafil, vardenafil) act to decrease the degradation of cGMP via phosphodiesterase (PDE) type 5 by inhibiting this enzyme, resulting in increased accumulation of cGMP and more pronounced smooth muscle relaxation and vasodilation than with either PDE type 5 inhibitors or nitrates/nitrites alone. This interaction probably occurs with any organic nitrate, nitrite, or nitric oxide donor (e.g., nitroprusside) regardless of their predominant hemodynamic site of action.","MeSH Headers":[{"Id":"M0265894","Link":"https://id.nlm.nih.gov/mesh/M0265894.html","Name":"Sildenafil","Ref":128},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":129},{"Id":"M0022559","Link":"https://id.nlm.nih.gov/mesh/M0022559.html","Name":"Vasodilator Agents","Ref":155},{"Id":"M0545665","Link":"https://id.nlm.nih.gov/mesh/M0545665.html","Name":"Phosphodiesterase 5 Inhibitors","Ref":156},{"Id":"M0584314","Link":"https://id.nlm.nih.gov/mesh/M0584314.html","Name":"Urological Agents","Ref":157}],"MeSH Pharmacological Classification":[{"Id":"M0022559","Link":"https://id.nlm.nih.gov/mesh/M0022559.html","Name":"Vasodilator Agent","Ref":155},{"Id":"M0545665","Link":"https://id.nlm.nih.gov/mesh/M0545665.html","Name":"Phosphodiesterase 5 Inhibitor","Ref":156},{"Id":"M0584314","Link":"https://id.nlm.nih.gov/mesh/M0584314.html","Name":"Urological Agent","Ref":157}],"Mechanism of Action":"Sildenafil is an oral therapy for erectile dysfunction. In the natural setting, i.e. with sexual stimulation, it restores impaired erectile function by increasing blood flow to the penis.  The physiological mechanism responsible for the erection of the penis involves the release of nitric oxide (NO) in the corpus cavernosum during sexual stimulation. Nitric oxide then activates the enzyme guanylate cyclase, which results in increased levels of cyclic guanosine monophosphate (cGMP), producing smooth muscle relaxation in the corpus cavernosum and allowing inflow of blood.  Sildenafil is a potent and selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5) in the corpus cavernosum, where PDE5 is responsible for degradation of cGMP. Sildenafil has a peripheral site of action on erections. Sildenafil has no direct relaxant effect on isolated human corpus cavernosum but potently enhances the relaxant effect of NO on this tissue. When the NO/cGMP pathway is activated, as occurs with sexual stimulation, inhibition of PDE5 by sildenafil results in increased corpus cavernosum levels of cGMP. Therefore sexual stimulation is required in order for sildenafil to produce its intended beneficial pharmacological effects.  Moreover, apart from the presence of PDE5 in the corpus cavernosum of the penis, PDE5 is also present in the pulmonary vasculature. Sildenafil, therefore, increases cGMP within pulmonary vascular smooth muscle cells resulting in relaxation. In patients with pulmonary arterial hypertension, this can lead to vasodilation of the pulmonary vascular bed and, to a lesser degree, vasodilatation in the systemic circulation.","Melting Point":"189-190 °C","Metabolism/Metabolites":"The metabolism of sildenafil is facilitated primarily by the CYP3A4 hepatic microsomal isoenzymes and to a minor extent, via the CYP2C9 hepatic isoenzymes. The predominant circulating metabolite results from the N-demethylation of sildenafil. This particular resultant metabolite possesses a phosphodiesterase selectivity that is similar to the parent sildenafil molecule and a corresponding in vitro potency for PDE5 that is approximately 50% that of the parent drug. Moreover, plasma concentrations of the metabolite are about 40% of those recorded for sildenafil, a percentage that accounts for about 20% of sildenafil’s pharmacologic effects. This primary N-desmethyl metabolite of sildenafil also undergoes further metabolism, with a terminal half-life of about 4 hours.  In patients with pulmonary arterial hypertension, plasma concentrations of the primary N-desmethyl metabolite are about 72% those of the original parent sildenafil molecule after a regimen of 20 mg three times a day - which is consequently responsible for about a 36% contribution to sildenafil’s overall pharmacological effects.","MolecularFormula":"C\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e30\u003c/sub\u003eN\u003csub\u003e6\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003eS","MolecularWeight":"474.6 g/mol","Pharmacodynamics":"In vitro studies have shown that sildenafil is selective for phosphodiesterase-5 (PDE5). Its effect is more potent on PDE5 than on other known phosphodiesterases. In particular, there is a 10-times selectivity over PDE6 which is involved in the phototransduction pathway in the retina. There is an 80-times selectivity over PDE1, and over 700-times over PDE 2, 3, 4, 7, 8, 9, 10 and 11. And finally, sildenafil has greater than 4,000-times selectivity for PDE5 over PDE3, the cAMP-specific phosphodiesterase isoform involved in the control of cardiac contractility.  In eight double-blind, placebo-controlled crossover studies of patients with either organic or psychogenic erectile dysfunction, sexual stimulation resulted in improved erections, as assessed by an objective measurement of hardness and duration of erections (via the use of RigiScan®), after sildenafil administration compared with placebo. Most studies assessed the efficacy of sildenafil approximately 60 minutes post-dose. The erectile response, as assessed by RigiScan®, generally increased with increasing sildenafil dose and plasma concentration. The time course of effect was examined in one study, showing an effect for up to 4 hours but the response was diminished compared to 2 hours.  Sildenafil causes mild and transient decreases in systemic blood pressure which, in the majority of cases, do not translate into clinical effects. After chronic dosing of 80 mg, three times a day to patients with systemic hypertension the mean change from baseline in systolic and diastolic blood pressure was a decrease of 9.4 mmHg and 9.1 mmHg respectively. After chronic dosing of 80 mg, three times a day to patients with pulmonary arterial hypertension lesser effects in blood pressure reduction were observed (a reduction in both systolic and diastolic pressure of 2 mmHg) . At the recommended dose of 20 mg three times a day no reductions in systolic or diastolic pressure were seen.  Single oral doses of sildenafil up to 100 mg in healthy volunteers produced no clinically relevant effects on ECG. After chronic dosing of 80 mg three times a day to patients with pulmonary arterial hypertension no clinically relevant effects on the ECG were reported either.  In a study of the hemodynamic effects of a single oral 100 mg dose of sildenafil in 14 patients with severe coronary artery disease (CAD) (\u003e 70 % stenosis of at least one coronary artery), the mean resting systolic and diastolic blood pressures decreased by 7 % and 6 % respectively compared to baseline. Mean pulmonary systolic blood pressure decreased by 9%. Sildenafil showed no effect on cardiac output and did not impair blood flow through the stenosed coronary arteries.  Mild and transient differences in color discrimination (blue/green) were detected in some subjects using the Farnsworth-Munsell 100 hue test at 1 hour following a 100 mg dose, with no effects evident after 2 hours post-dose. The postulated mechanism for this change in color discrimination is related to inhibition of PDE6, which is involved in the phototransduction cascade of the retina. Sildenafil has no effect on visual acuity or contrast sensitivity. In a small size placebo-controlled study of patients with documented early age-related macular degeneration (n = 9), sildenafil (single dose, 100 mg) demonstrated no significant changes in visual tests conducted (which included visual acuity, Amsler grid, color discrimination simulated traffic light, and the Humphrey perimeter and photostress test).","Physical Description":"Solid","PubChemId":135398744,"PubChemTitle":"Sildenafil","Record Description":["LiverTox|Urologic|Erectile Dysfunction|PDE-3 inhibitor"],"Records":{"UNII":{"Impurities":[]}},"Reddit Experience Reports":[],"RefChem":"6218","RefCount":5,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Sildenafil","Name":"Sildenafil","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q191521","Name":"Sildenafil","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB00203","Name":"Sildenafil","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/135398744","Name":"Sildenafil","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=139755-83-2","Name":"Sildenafil","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0005039","Name":"Sildenafil","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C07259","Name":"Sildenafil","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/3M7OB98Y7H","Name":"Sildenafil","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID6023579","Name":"Sildenafil","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 135398744, Sildenafil. Accessed August 24, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/135398744\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/135398744\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Sildenafil. UNII: 3M7OB98Y7H. Global Substance Registration System. Accessed August 24, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/3M7OB98Y7H\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/3M7OB98Y7H\u003c/a\u003e","Viagra 25mg film-coated tablets Summary of Product Characteristics (SmPC). September 30, 2024. Accessed August 24, 2026. \u003ca href=https://www.medicines.org.uk/emc/product/1072/smpc\u003ehttps://www.medicines.org.uk/emc/product/1072/smpc\u003c/a\u003e","Viagra Connect 50 mg film-coated tablets Summary of Product Characteristics (SmPC). May 16, 2024. Accessed August 24, 2026. \u003ca href=https://www.medicines.org.uk/emc/product/8725/smpc\u003ehttps://www.medicines.org.uk/emc/product/8725/smpc\u003c/a\u003e"],"SMILES":"CCCC1=NN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)C)OCC)C","SaltData":[{"AcidCount":1,"Amine":"Sildenafil","AmineCount":1,"Formula":"C(C(=O)O)C(CC(=O)O)(C(=O)O)O","Name":"citrate","RName":"citrate","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 210.69 116.367\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".8\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h211v117H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m135.918 98.843-4.699-14.497M131.219 84.346l-14.905-3.18M116.314 81.166l-4.698-14.498\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m111.616 66.668 6.195-8.483M110.688 63.805l5.154-7.058\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m117.811 58.185-3.097 4.242M115.842 56.747l-2.577 3.529\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m117.851 50.592-3.457-4.813M108.25 43.094l-11.124 3.632\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m97.096 61.966.03-15.24M94.661 60.558l.024-12.429\"/\u003e\u003c/g\u003e\u003cpath d=\"m111.616 66.668-14.52-4.702M97.096 61.966l-9.843 5.697\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m70.68 61.914 10.015 5.759M73.121 60.505l8.789 5.055\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m80.695 67.673-5.007-2.88M81.91 65.56l-4.394-2.528\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m70.68 61.914.022-11.14M73.991 44.79l9.942-5.71M97.126 46.726 83.933 39.08\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m82.713 39.781.023-11.751M85.151 39.786l.023-11.751\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m82.736 28.03-.011 5.876M85.174 28.035l-.012 5.875\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m70.68 61.914-13.199 7.618\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m57.476 84.78.005-15.248M55.038 83.372l.004-12.433\"/\u003e\u003c/g\u003e\u003cpath d=\"m57.476 84.78-13.203 7.629\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m31.075 84.789 13.198 7.62M33.513 83.381l10.759 6.212\"/\u003e\u003c/g\u003e\u003cpath d=\"m31.075 84.789.004-15.249\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M44.283 61.912 31.079 69.54M44.283 64.727l-10.766 6.221\"/\u003e\u003c/g\u003e\u003cpath d=\"m57.481 69.532-13.198-7.62M31.079 69.54l-10.053-5.804\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M14.336 62.533 6.55 61.16M14.76 60.132l-7.787-1.373\"/\u003e\u003cpath stroke=\"#c6c62c\" d=\"m14.336 62.533-3.893-.687\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m6.55 61.16 3.893.686\" class=\"hi\"/\u003e\u003cpath stroke=\"#c6c62c\" d=\"m14.76 60.132-3.893-.687\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m6.973 58.759 3.894.686\" class=\"hi\"/\u003e\u003c/g\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m17.565 66.352-2.26 6.21M15.274 65.518l-2.26 6.21\"/\u003e\u003cpath stroke=\"#c6c62c\" d=\"m17.565 66.352-1.13 3.105\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m15.305 72.562 1.13-3.105\" class=\"hi\"/\u003e\u003cpath stroke=\"#c6c62c\" d=\"m15.274 65.518-1.13 3.105\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m13.014 71.728 1.13-3.105\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"M17.881 57.727v-6.946M21.16 44.788l9.929-5.728M31.089 39.06V23.82M31.089 23.82l-9.929-5.728M14.602 18.092 4.673 23.82M4.673 23.82v15.24M14.602 44.788 4.673 39.06M17.881 12.1V.96M57.476 84.78l9.59 5.537M70.674 96.593v11.047M70.674 107.64l13.198 7.62M112.98 37.958l3.423-10.463\" class=\"bond\"/\u003e\u003cpath fill=\"#3050f8\" stroke=\"none\" d=\"M118.688 51.892h.911l2.214 4.185v-4.185h.661v5.001h-.911l-2.22-4.185v4.185h-.655zM109.771 39.479h.911l2.215 4.185v-4.185h.661v5.001h-.911l-2.221-4.185v4.185h-.655zM82.082 67.06h.911l2.214 4.185V67.06h.661v5h-.911l-2.22-4.185v4.185h-.655z\" class=\"atom\"/\u003e\u003cg fill=\"#3050f8\" stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M68.817 44.173h.911l2.215 4.185v-4.185h.66v5.001h-.91l-2.221-4.185v4.185h-.655zM64.436 44.173h.678v2.048h2.459v-2.048h.673v5.001h-.673v-2.381h-2.459v2.381h-.678z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"none\" d=\"M83.967 21.795q-.739 0-1.173.554-.429.547-.429 1.494 0 .946.429 1.494.434.548 1.173.548.738 0 1.166-.548.429-.548.429-1.494 0-.947-.429-1.494-.428-.554-1.166-.554m0-.548q1.053 0 1.678.709.631.702.631 1.887 0 1.179-.631 1.887-.625.702-1.678.702-1.054 0-1.685-.702t-.631-1.887.631-1.887q.631-.709 1.685-.709\" class=\"atom\"/\u003e\u003cpath fill=\"#c6c62c\" stroke=\"none\" d=\"M19.343 59.583v.661q-.387-.184-.732-.274-.34-.095-.655-.095-.554 0-.858.214-.297.215-.297.614 0 .327.196.5.203.166.756.274l.411.083q.756.143 1.113.506.363.363.363.97 0 .727-.488 1.102t-1.428.375q-.352 0-.757-.084-.398-.077-.827-.232v-.696q.417.232.81.351.393.113.774.113.583 0 .892-.226.316-.226.316-.649 0-.369-.226-.578-.22-.208-.738-.309l-.411-.084q-.756-.148-1.096-.47-.339-.321-.339-.893 0-.667.464-1.048.471-.381 1.292-.381.352 0 .715.066.363.059.75.19\" class=\"atom\"/\u003e\u003cpath stroke=\"none\" d=\"M2.876 57.229q-.738 0-1.173.553-.429.548-.429 1.495 0 .946.429 1.494.435.548 1.173.548t1.167-.548q.428-.548.428-1.494 0-.947-.428-1.495-.429-.553-1.167-.553m0-.548q1.053 0 1.679.708.631.703.631 1.888 0 1.178-.631 1.887-.626.702-1.679.702-1.054 0-1.685-.702-.631-.703-.631-1.887t.631-1.888q.631-.708 1.685-.708M12.672 74.196q-.738 0-1.173.554-.429.547-.429 1.494 0 .946.429 1.494.435.548 1.173.548t1.167-.548.428-1.494q0-.947-.428-1.494-.429-.554-1.167-.554m0-.548q1.054 0 1.679.709.631.702.631 1.887 0 1.179-.631 1.887-.625.703-1.679.703t-1.685-.703q-.631-.702-.631-1.887t.631-1.887q.631-.709 1.685-.709\" class=\"atom\"/\u003e\u003cpath fill=\"#3050f8\" stroke=\"none\" d=\"M15.988 44.18h.911l2.215 4.185V44.18h.66v5h-.91l-2.221-4.185v4.185h-.655zM15.988 13.7h.911l2.215 4.185V13.7h.66v5h-.91l-2.221-4.185V18.7h-.655z\" class=\"atom\"/\u003e\u003cpath stroke=\"none\" d=\"M70.677 90.355q-.738 0-1.173.554-.428.547-.428 1.494t.428 1.494q.435.548 1.173.548t1.167-.548q.429-.547.429-1.494t-.429-1.494q-.429-.554-1.167-.554m0-.548q1.054 0 1.679.709.631.702.631 1.887 0 1.179-.631 1.887-.625.703-1.679.703t-1.685-.703q-.631-.702-.631-1.887t.631-1.887q.631-.709 1.685-.709\" class=\"atom\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m117.851 50.592-1.728-2.406M108.25 43.094l-5.562 1.816M87.253 67.663l4.921-2.849M70.702 50.774l-.011 5.57M73.991 44.79l4.971-2.855\" class=\"hi\"/\u003e\u003cpath stroke=\"#c6c62c\" d=\"m21.026 63.736 5.027 2.902M17.881 57.727v-3.473\" class=\"hi\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"M17.881 50.781v3.473M21.16 44.788l4.964-2.864M21.16 18.092l4.964 2.864M14.602 18.092l-4.965 2.864M14.602 44.788l-4.965-2.864M17.881 12.1V6.53\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m67.066 90.317-4.795-2.769M70.674 96.593v5.524\" class=\"hi\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m112.98 37.958 1.712-5.231\" class=\"hi\"/\u003e\u003c/g\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m183.012 69.613-13.198 7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M171.033 76.529V88.28M168.595 76.529V88.28\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"M171.033 88.28v-5.876M168.595 88.28v-5.876\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m169.814 77.233-9.59-5.536M183.012 69.613v-15.24M183.012 54.373l-13.198-7.62M169.814 46.753v-15.24\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m168.595 30.809 10.196-5.887M169.814 32.921l10.197-5.887\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m178.791 24.922-5.098 2.944M180.011 27.034l-5.099 2.943\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m169.814 31.513-9.59-5.536M183.012 54.373l15.009 2.647\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m196.634 56.775 7.588-9.042M198.502 58.343l7.588-9.043\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m204.222 47.733-3.794 4.521M206.09 49.3l-3.794 4.522\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m198.021 57.02 3.721 10.224M183.012 54.373l3.722-10.224\" class=\"bond\"/\u003e\u003cpath stroke=\"none\" d=\"M169.817 90.428q-.738 0-1.173.554-.428.548-.428 1.494 0 .947.428 1.494.435.548 1.173.548t1.167-.548q.428-.547.428-1.494 0-.946-.428-1.494-.429-.554-1.167-.554m0-.547q1.054 0 1.679.708.631.703.631 1.887 0 1.179-.631 1.887-.625.703-1.679.703t-1.685-.703q-.631-.702-.631-1.887 0-1.184.631-1.887.631-.708 1.685-.708\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M156.619 67.568q-.738 0-1.173.554-.429.548-.429 1.494 0 .947.429 1.494.435.548 1.173.548t1.167-.548q.428-.547.428-1.494 0-.946-.428-1.494-.429-.554-1.167-.554m0-.547q1.053 0 1.678.708.632.703.632 1.887 0 1.179-.632 1.887-.625.703-1.678.703-1.054 0-1.685-.703-.631-.702-.631-1.887 0-1.184.631-1.887.631-.708 1.685-.708M149.921 67.11h.679v2.048h2.459V67.11h.672v5.001h-.672v-2.382H150.6v2.382h-.679z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"none\" d=\"M183.015 21.848q-.738 0-1.173.554-.428.548-.428 1.494 0 .947.428 1.494.435.548 1.173.548t1.167-.548q.429-.547.429-1.494 0-.946-.429-1.494-.429-.554-1.167-.554m0-.547q1.054 0 1.679.708.631.703.631 1.887 0 1.179-.631 1.887-.625.703-1.679.703t-1.685-.703-.631-1.887.631-1.887q.631-.708 1.685-.708\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M156.619 21.848q-.738 0-1.173.554-.429.548-.429 1.494 0 .947.429 1.494.435.548 1.173.548t1.167-.548q.428-.547.428-1.494 0-.946-.428-1.494-.429-.554-1.167-.554m0-.547q1.053 0 1.678.708.632.703.632 1.887 0 1.179-.632 1.887-.625.703-1.678.703-1.054 0-1.685-.703-.631-.702-.631-1.887 0-1.184.631-1.887.631-.708 1.685-.708M149.921 21.39h.679v2.048h2.459V21.39h.672v5.001h-.672v-2.382H150.6v2.382h-.679z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"none\" d=\"M207.82 43.3q-.738 0-1.173.554-.429.548-.429 1.494 0 .947.429 1.494.435.548 1.173.548t1.167-.548q.428-.547.428-1.494 0-.946-.428-1.494-.429-.554-1.167-.554m0-.547q1.053 0 1.678.708.632.702.632 1.887 0 1.179-.632 1.887-.625.703-1.678.703-1.054 0-1.685-.703-.631-.702-.631-1.887t.631-1.887q.631-.708 1.685-.708\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M203.236 69.296q-.738 0-1.173.553-.428.548-.428 1.495 0 .946.428 1.494.435.547 1.173.547t1.167-.547q.428-.548.428-1.494 0-.947-.428-1.495-.429-.553-1.167-.553m0-.548q1.054 0 1.679.708.631.703.631 1.888 0 1.178-.631 1.887-.625.702-1.679.702t-1.685-.702q-.631-.703-.631-1.887t.631-1.888q.631-.708 1.685-.708M206.117 68.837h.679v2.048h2.459v-2.048h.672v5.001h-.672v-2.381h-2.459v2.381h-.679z\"/\u003e\u003c/g\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M188.228 38.007q-.739 0-1.173.554-.429.548-.429 1.494 0 .947.429 1.495.434.547 1.173.547.738 0 1.166-.547.429-.548.429-1.495 0-.946-.429-1.494-.428-.554-1.166-.554m0-.547q1.053 0 1.678.708.631.703.631 1.887 0 1.179-.631 1.887-.625.703-1.678.703-1.054 0-1.685-.703-.631-.702-.631-1.887 0-1.184.631-1.887.631-.708 1.685-.708M191.109 37.549h.679v2.048h2.458v-2.048h.673v5.001h-.673v-2.382h-2.458v2.382h-.679z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m160.224 71.697 4.795 2.768M160.224 25.977l4.795 2.768M201.742 67.244l-1.861-5.112M201.742 67.244l-1.861-5.112M186.734 44.149l-1.861 5.112\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"Sildenafil citrate","UNII":"BW9B0ZE037"}],"Salts":["citrate"],"Scheduling":[{"gov":"Australia","ref":[],"schedule":"S4 substance"},{"gov":"Canada","ref":[],"schedule":"prescription only substance"},{"gov":"United Kingdom","ref":["3","4"],"schedule":"prescription only substance"},{"gov":"United States","ref":[],"schedule":"prescription only substance"},{"gov":"European Union","ref":[],"schedule":"prescription only substance"}],"Solubility":"White to off-white crystalline powder; solubility in water: 3.5 mg/mL /Sildenafil citrate/","Stability/Shelf Life":"Reconstituted sildenafil oral suspension is stable for 30 days when stored as directed; any remaining suspension should be discarded after that time.","StereoisomerData":[],"Stereoisomers":[],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 136.981 116.367\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".8\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h137v117H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m135.918 98.843-4.699-14.497M131.219 84.346l-14.905-3.18M116.314 81.166l-4.698-14.498\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m111.616 66.668 6.195-8.483M110.688 63.805l5.154-7.058\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m117.811 58.185-3.097 4.242M115.842 56.747l-2.577 3.529\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m117.851 50.592-3.457-4.813M108.25 43.094l-11.124 3.632\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m97.096 61.966.03-15.24M94.661 60.558l.024-12.429\"/\u003e\u003c/g\u003e\u003cpath d=\"m111.616 66.668-14.52-4.702M97.096 61.966l-9.843 5.697\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m70.68 61.914 10.015 5.759M73.121 60.505l8.789 5.055\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m80.695 67.673-5.007-2.88M81.91 65.56l-4.394-2.528\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m70.68 61.914.022-11.14M73.991 44.79l9.942-5.71M97.126 46.726 83.933 39.08\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m82.713 39.781.023-11.751M85.151 39.786l.023-11.751\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m82.736 28.03-.011 5.876M85.174 28.035l-.012 5.875\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m70.68 61.914-13.199 7.618\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m57.476 84.78.005-15.248M55.038 83.372l.004-12.433\"/\u003e\u003c/g\u003e\u003cpath d=\"m57.476 84.78-13.203 7.629\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m31.075 84.789 13.198 7.62M33.513 83.381l10.759 6.212\"/\u003e\u003c/g\u003e\u003cpath d=\"m31.075 84.789.004-15.249\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M44.283 61.912 31.079 69.54M44.283 64.727l-10.766 6.221\"/\u003e\u003c/g\u003e\u003cpath d=\"m57.481 69.532-13.198-7.62M31.079 69.54l-10.053-5.804\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M14.336 62.533 6.55 61.16M14.76 60.132l-7.787-1.373\"/\u003e\u003cpath stroke=\"#c6c62c\" d=\"m14.336 62.533-3.893-.687\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m6.55 61.16 3.893.686\" class=\"hi\"/\u003e\u003cpath stroke=\"#c6c62c\" d=\"m14.76 60.132-3.893-.687\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m6.973 58.759 3.894.686\" class=\"hi\"/\u003e\u003c/g\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m17.565 66.352-2.26 6.21M15.274 65.518l-2.26 6.21\"/\u003e\u003cpath stroke=\"#c6c62c\" d=\"m17.565 66.352-1.13 3.105\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m15.305 72.562 1.13-3.105\" class=\"hi\"/\u003e\u003cpath stroke=\"#c6c62c\" d=\"m15.274 65.518-1.13 3.105\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m13.014 71.728 1.13-3.105\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"M17.881 57.727v-6.946M21.16 44.788l9.929-5.728M31.089 39.06V23.82M31.089 23.82l-9.929-5.728M14.602 18.092 4.673 23.82M4.673 23.82v15.24M14.602 44.788 4.673 39.06M17.881 12.1V.96M57.476 84.78l9.59 5.537M70.674 96.593v11.047M70.674 107.64l13.198 7.62M112.98 37.958l3.423-10.463\" class=\"bond\"/\u003e\u003cpath stroke=\"none\" d=\"M118.688 51.892h.911l2.214 4.185v-4.185h.661v5.001h-.911l-2.22-4.185v4.185h-.655zM109.771 39.479h.911l2.215 4.185v-4.185h.661v5.001h-.911l-2.221-4.185v4.185h-.655zM82.082 67.06h.911l2.214 4.185V67.06h.661v5h-.911l-2.22-4.185v4.185h-.655z\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M68.817 44.173h.911l2.215 4.185v-4.185h.66v5.001h-.91l-2.221-4.185v4.185h-.655zM64.436 44.173h.678v2.048h2.459v-2.048h.673v5.001h-.673v-2.381h-2.459v2.381h-.678z\"/\u003e\u003c/g\u003e\u003cpath fill=\"#ff0d0d\" stroke=\"none\" d=\"M83.967 21.795q-.739 0-1.173.554-.429.547-.429 1.494 0 .946.429 1.494.434.548 1.173.548.738 0 1.166-.548.429-.548.429-1.494 0-.947-.429-1.494-.428-.554-1.166-.554m0-.548q1.053 0 1.678.709.631.702.631 1.887 0 1.179-.631 1.887-.625.702-1.678.702-1.054 0-1.685-.702t-.631-1.887.631-1.887q.631-.709 1.685-.709\" class=\"atom\"/\u003e\u003cpath fill=\"#c6c62c\" stroke=\"none\" d=\"M19.343 59.583v.661q-.387-.184-.732-.274-.34-.095-.655-.095-.554 0-.858.214-.297.215-.297.614 0 .327.196.5.203.166.756.274l.411.083q.756.143 1.113.506.363.363.363.97 0 .727-.488 1.102t-1.428.375q-.352 0-.757-.084-.398-.077-.827-.232v-.696q.417.232.81.351.393.113.774.113.583 0 .892-.226.316-.226.316-.649 0-.369-.226-.578-.22-.208-.738-.309l-.411-.084q-.756-.148-1.096-.47-.339-.321-.339-.893 0-.667.464-1.048.471-.381 1.292-.381.352 0 .715.066.363.059.75.19\" class=\"atom\"/\u003e\u003cpath fill=\"#ff0d0d\" stroke=\"none\" d=\"M2.876 57.229q-.738 0-1.173.553-.429.548-.429 1.495 0 .946.429 1.494.435.548 1.173.548t1.167-.548q.428-.548.428-1.494 0-.947-.428-1.495-.429-.553-1.167-.553m0-.548q1.053 0 1.679.708.631.703.631 1.888 0 1.178-.631 1.887-.626.702-1.679.702-1.054 0-1.685-.702-.631-.703-.631-1.887t.631-1.888q.631-.708 1.685-.708M12.672 74.196q-.738 0-1.173.554-.429.547-.429 1.494 0 .946.429 1.494.435.548 1.173.548t1.167-.548.428-1.494q0-.947-.428-1.494-.429-.554-1.167-.554m0-.548q1.054 0 1.679.709.631.702.631 1.887 0 1.179-.631 1.887-.625.703-1.679.703t-1.685-.703q-.631-.702-.631-1.887t.631-1.887q.631-.709 1.685-.709\" class=\"atom\"/\u003e\u003cpath stroke=\"none\" d=\"M15.988 44.18h.911l2.215 4.185V44.18h.66v5h-.91l-2.221-4.185v4.185h-.655zM15.988 13.7h.911l2.215 4.185V13.7h.66v5h-.91l-2.221-4.185V18.7h-.655z\" class=\"atom\"/\u003e\u003cpath fill=\"#ff0d0d\" stroke=\"none\" d=\"M70.677 90.355q-.738 0-1.173.554-.428.547-.428 1.494t.428 1.494q.435.548 1.173.548t1.167-.548q.429-.547.429-1.494t-.429-1.494q-.429-.554-1.167-.554m0-.548q1.054 0 1.679.709.631.702.631 1.887 0 1.179-.631 1.887-.625.703-1.679.703t-1.685-.703q-.631-.702-.631-1.887t.631-1.887q.631-.709 1.685-.709\" class=\"atom\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m117.851 50.592-1.728-2.406M108.25 43.094l-5.562 1.816M87.253 67.663l4.921-2.849M70.702 50.774l-.011 5.57M73.991 44.79l4.971-2.855\" class=\"hi\"/\u003e\u003cpath stroke=\"#c6c62c\" d=\"m21.026 63.736 5.027 2.902M17.881 57.727v-3.473\" class=\"hi\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"M17.881 50.781v3.473M21.16 44.788l4.964-2.864M21.16 18.092l4.964 2.864M14.602 18.092l-4.965 2.864M14.602 44.788l-4.965-2.864M17.881 12.1V6.53\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m67.066 90.317-4.795-2.769M70.674 96.593v5.524\" class=\"hi\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m112.98 37.958 1.712-5.231\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Therapeutic Uses":"Phosphodiesterase 5 Inhibitors; Urological Agents; Vasodilator Agents","Title":"Sildenafil","UNII":"3M7OB98Y7H","Wikidata":"Q191521","Wikipedia":"Sildenafil","XLogP":1.5}
