Sildenafil (CED0002006)

Record Information
Version1.0
Creation Date2016-05-26 06:42:54 UTC
Update Date2026-08-21 22:56:20 UTC
Accession NumberCHEM035843
Identification
Common NameSildenafil
ClassSmall Molecule
Description
Sildenafil is an organic compound with the formula C22H30N6O4S and an average molecular weight of 474.58 g/mol. Sildenafil belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. This compound is associated with four recorded sources, including antennas in electrical and electronic equipment, drinking water in drinking water and water supply, and gynecologicals and urologicals in healthcare, pharmaceuticals and veterinary products. Recorded exposure routes for this substance include oral and intravenous administration. Sildenafil interacts with six recorded protein targets. It acts as a modulator, inhibitor, or downregulator of cGMP-specific 3',5'-cyclic phosphodiesterase (PDE5A). Additional protein targets include ornithine decarboxylase (ODC1), retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma (PDE6H), and retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma (PDE6G), as well as two other proteins.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazineChEBI
AphrodilKegg
1-((3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulphonyl)-4-methylpiperazineGenerator
CavertaHMDB
RevatioHMDB
Sildenafil citrateHMDB
ViagraHMDB
Desmethyl sildenafilHMDB
HydroxyhomosildenafilHMDB
1-((3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo(4,3-D)pyrimidin-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methylpiperazine citrateHMDB
Lactate, sildenafilHMDB
NCX-911HMDB
Nitrate, sildenafilHMDB
AcetildenafilHMDB
Sildenafil nitrateHMDB
NCX 911HMDB
HomosildenafilHMDB
Citrate, sildenafilHMDB
Sildenafil, desmethylHMDB
DesmethylsildenafilHMDB
Sildenafil lactateHMDB
Chemical FormulaC22H30N6O4S
Average Molecular Mass474.576 g/mol
Monoisotopic Mass474.205 g/mol
CAS Registry Number139755-83-2
IUPAC Name5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one
Traditional Namerevatio
SMILESCCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1
InChI IdentifierInChI=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)
InChI KeyBNRNXUUZRGQAQC-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Pyrazolopyrimidine
  • Benzenesulfonyl group
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Pyrimidone
  • N-methylpiperazine
  • N-alkylpiperazine
  • Piperazine
  • Pyrimidine
  • Organosulfonic acid amide
  • 1,4-diazinane
  • Pyrazole
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Azole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Lactam
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.43 g/LALOGPS
logP2.35ALOGPS
logP1.65ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.27ChemAxon
pKa (Strongest Basic)5.97ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area109.13 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity139.44 m³·mol⁻¹ChemAxon
Polarizability51.18 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-006t-9004300000-55c87eff7b6ad40ea3d5Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0059-2494500000-e3f8387aee5a0463363cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05s0-3892000000-aa19715309275e16a6c0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0059-2494500000-e3f8387aee5a0463363cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05s0-3892000000-aa19715309275e16a6c0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0002900000-b281f59f40caaba85ac9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-4436900000-0c5804e76b9d495c76d6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0459-6292000000-5a32bfcdda2067978be9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0001900000-51b4957d0b3d25c41773Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01vk-0302900000-86c63c2fd17f7c5b7d6fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-8916100000-e941afc576d544ed32a7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0000900000-c92b21b6524ea5040313Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0000900000-06d94f4626e8bee6e389Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006t-9101300000-ef50cfadb7bd34e88187Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0000900000-1617a2dfdf2b96a0cd2cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0010900000-744efa093f1de0f36d62Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-003r-0272900000-aa5d9fef9c0fb52ad923Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2347.0Log mg/kg[1300:4200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
326UrologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
2 pathways
Sildenafil Action Pathway
Sildenafil Action Pathway
Sildenafil Drug Metabolism Action Pathway
Sildenafil Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureCone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'P16586Bos taurusPredicted (SEA)0.155698
cGMP-specific 3',5'-cyclic phosphodiesterase structureClick to view 3D structurecGMP-specific 3',5'-cyclic phosphodiesteraseO76074HumansPredicted (SEA)2.56902
ATP-binding cassette sub-family C member 5 structureClick to view 3D structureATP-binding cassette sub-family C member 5O15440HumansPredicted (SEA)0.155698
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A structureClick to view 3D structureHigh affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9AO76083HumansPredicted (SEA)2.80257
Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha' structureClick to view 3D structureCone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'P51160HumansPredicted (SEA)0.934191
Click to view 3D structurePhosphodiesteraseQ53I60Trypanosoma cruziPredicted (SEA)0.700643
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A structureClick to view 3D structurecAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10AQ9Y233HumansPredicted (SEA)4.20386
Click to view 3D structureDual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11AQ9HCR9HumansPredicted (SEA)2.80257
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A structureClick to view 3D structureHigh affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8AO60658HumansPredicted (SEA)1.08989
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A structureClick to view 3D structureHigh affinity 3',5'-cyclic-AMP phosphodiesterase 7AQ13946HumansPredicted (SEA)1.63483
Adenosine receptor A1 structureClick to view 3D structureAdenosine receptor A1P30542HumansPredicted (SEA)50.9134
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)54.5723
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)57.842
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A structureClick to view 3D structurecGMP-inhibited 3',5'-cyclic phosphodiesterase 3AQ14432HumansPredicted (SEA)6.77288
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)68.1959
cGMP-dependent 3',5'-cyclic phosphodiesterase structureClick to view 3D structurecGMP-dependent 3',5'-cyclic phosphodiesteraseO00408HumansPredicted (SEA)9.34191
Histone deacetylase 2 structureClick to view 3D structureHistone deacetylase 2Q92769HumansPredicted (SEA)69.4415
3',5'-cyclic-AMP phosphodiesterase 4A structureClick to view 3D structure3',5'-cyclic-AMP phosphodiesterase 4AP27815HumansPredicted (SEA)9.57545
Click to view 3D structureDual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AP54750HumansPredicted (SEA)2.95827
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)444.597
Click to view 3D structureRod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alphaQ28263Canis lupus familiarisPredicted (SEA)0.778492
Click to view 3D structurecGMP-specific 3',5'-cyclic phosphodiesteraseO54735Rattus norvegicusPredicted (SEA)2.80257
Adenosine receptor A2b structureClick to view 3D structureAdenosine receptor A2bP29275HumansPredicted (SEA)113.426
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)204.51
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)232.069
Concentrations
Not Available
External Links
DrugBank IDDB00203
HMDB IDHMDB0005039
FooDB IDFDB023606
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSildenafil
Chemspider ID5023
ChEBI ID9139
PubChem Compound ID5212
Kegg Compound IDC07259
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Dunn, Peter James; Wood, Albert Shaw. Process for preparation of Sildenafil by cyclization. Eur. Pat. Appl. (1997), 18 pp.
2. Kim NN, Goldstein I, Moreland RB, Traish AM: Alpha-adrenergic receptor blockade by phentolamine increases the efficacy of vasodilators in penile corpus cavernosum. Int J Impot Res. 2000 Mar;12 Suppl 1:S26-36.
3. Warrington JS, Shader RI, von Moltke LL, Greenblatt DJ: In vitro biotransformation of sildenafil (Viagra): identification of human cytochromes and potential drug interactions. Drug Metab Dispos. 2000 Apr;28(4):392-7.
4. Chua R, Keogh A, Miyashita M: Novel use of sildenafil in the treatment of portopulmonary hypertension. J Heart Lung Transplant. 2005 Apr;24(4):498-500.
5. Fekete F, Fabian E: [Effectiveness and adverse effects of sildenafil in erectile dysfunction]. Orv Hetil. 2000 Jan 16;141(3):115-8.
6. Blount MA, Beasley A, Zoraghi R, Sekhar KR, Bessay EP, Francis SH, Corbin JD: Binding of tritiated sildenafil, tadalafil, or vardenafil to the phosphodiesterase-5 catalytic site displays potency, specificity, heterogeneity, and cGMP stimulation. Mol Pharmacol. 2004 Jul;66(1):144-52.
7. Kekilli M, Beyazit Y, Purnak T, Dogan S, Atalar E: Acute myocardial infarction after sildenafil citrate ingestion. Ann Pharmacother. 2005 Jul-Aug;39(7-8):1362-4. Epub 2005 May 24.