Vardenafil (CED0004973)

Record Information
Version1.0
Creation Date2016-05-25 18:23:17 UTC
Update Date2026-08-22 01:49:55 UTC
Accession NumberCHEM022191
Identification
Common NameVardenafil
ClassSmall Molecule
Description
Vardenafil is an organic compound with the chemical formula C23H32N6O4S and an average molecular weight of 488.60 g/mol. Vardenafil belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. This substance is recorded as being found in or released from three sources: antennas within electrical and electronic equipment, drinking water and water supply, and urologicals within healthcare, pharmaceuticals and veterinary products. The recorded exposure route for this compound is oral. At the molecular level, vardenafil acts upon three recorded protein targets. It serves as an inhibitor and allosteric modulator of cGMP-specific 3',5'-cyclic phosphodiesterase (PDE5A). Additionally, it targets the retinal cone rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma (PDE6H) and the retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma (PDE6G).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propylimidazo[5,1-F][1,2,4]triazin-4(1H)-oneChEBI
LevitraChEBI
2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulphonyl]phenyl}-5-methyl-7-propylimidazo[5,1-F][1,2,4]triazin-4(1H)-oneGenerator
VDNHMDB
Trihydrate, vardenafil hydrochlorideHMDB
Dihydrochloride, vardenafilHMDB
Vardenafil hydrochlorideHMDB
Vardenafil hydrochloride anhydrousHMDB
Vardenafil hydrochloride trihydrateHMDB
Anhydrous, vardenafil hydrochlorideHMDB
Hydrochloride anhydrous, vardenafilHMDB
Hydrochloride trihydrate, vardenafilHMDB
Hydrochloride, vardenafilHMDB
1-(((3-(3,4-Dihydro-5-methyl)-4-oxo-7-propylimidazo(5,1-F)-as-triazin-2-yl)-4-ethoxyphenyl)sulfonyl)-4-ethylpiperazineHMDB
Vardenafil dihydrochlorideHMDB
Chemical FormulaC23H32N6O4S
Average Molecular Mass488.603 g/mol
Monoisotopic Mass488.221 g/mol
CAS Registry Number224785-90-4
IUPAC Name2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propyl-1H,4H-imidazo[4,3-f][1,2,4]triazin-4-one
Traditional Namelevitra
SMILESCCCC1=NC(C)=C2N1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(CC)CC1
InChI IdentifierInChI=1S/C23H32N6O4S/c1-5-8-20-24-16(4)21-23(30)25-22(26-29(20)21)18-15-17(9-10-19(18)33-7-3)34(31,32)28-13-11-27(6-2)12-14-28/h9-10,15H,5-8,11-14H2,1-4H3,(H,25,26,30)
InChI KeySECKRCOLJRRGGV-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
  • Benzenesulfonyl group
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • N-alkylpiperazine
  • 1,4-diazinane
  • N-substituted imidazole
  • Piperazine
  • Organosulfonic acid amide
  • Triazine
  • 1,2,4-triazine
  • Heteroaromatic compound
  • Sulfonyl
  • Azole
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Imidazole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • 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 Solubility0.32 g/LALOGPS
logP2.18ALOGPS
logP1.33ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.01ChemAxon
pKa (Strongest Basic)6.21ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area109.13 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity142.71 m³·mol⁻¹ChemAxon
Polarizability53.22 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 Spectrumsplash10-03di-9304600000-78a6e2bde8e38b367f38Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0040900000-a78a646244f2fb1f6276Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000f-0011900000-88f62b9a8f7aec917a41Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0092000000-cf98ecae287c01370dbcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-0000900000-9008f3921907d4675261Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0000900000-1fcc6df6cdb6126d7ef0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-055r-0091200000-d63a9cf854a198162e08Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0000900000-93d391256ac331406facNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1924200000-417e1644b94601dd7f35Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0000900000-b883d879992fbedff256Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0090200000-050ed3eecf1ffddad8e3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0925000000-41aba03d13dfc7df8fafNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0413900000-e1526827ae9f58ddf244Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052r-0000900000-e5ff9d0dc7199d2f0c84Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0000900000-e10263c8f866f8b725eaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-3100900000-665b3066495254822a6cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0000900000-3b1c3b5e3ebaf21ef591Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0000900000-99f18e7a2ea26f21682bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-055r-0091200000-74cac0a8c4e6f18b2567Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0000900000-7205fafb37f359d4065dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0000900000-26041f0a936f9bcd9f1fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0031900000-7931333e43ecbe70cc38Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0040900000-9636f4acc671a7bdacf0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0002900000-c0cecdb93e99efbd369eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01w0-3536900000-89e4ca7c7d6e6e2e281eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02ai-5492100000-78d239c94528460e3603Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0000900000-caa7e887e43db6fbbc44Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0570-0412900000-c93873d3bd3336545c26Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ot-3900000000-b864d4adedbfa7b24b3bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0000900000-544de06c7e1000f39842Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0000900000-c408e617b92509f49ec1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01w0-5802900000-91154c4692dc9b749b57Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0000900000-9ff949ec2f205a0ac60aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0000900000-44e8a63046aca192819bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0344900000-921a580e2629a123a3bcNot 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
2637.0Log mg/kg[1500:4700]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
326UrologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
2 pathways
Vardenafil Drug Metabolism Action Pathway
Vardenafil Drug Metabolism Action Pathway
Vardenafil Predicted Metabolism Pathway
Vardenafil Predicted Metabolism Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha' structureClick to view 3D structureCone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'P51160HumansPredicted (SEA)4.43741
Click to view 3D structurePhosphodiesteraseQ53I60Trypanosoma cruziPredicted (SEA)1.94623
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)19.3845
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)5.76084
Click to view 3D structureDual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11AQ9HCR9HumansPredicted (SEA)10.2761
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A structureClick to view 3D structureHigh affinity 3',5'-cyclic-AMP phosphodiesterase 7AQ13946HumansPredicted (SEA)11.5995
Click to view 3D structureRod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alphaQ28263Canis lupus familiarisPredicted (SEA)1.01204
cGMP-dependent 3',5'-cyclic phosphodiesterase structureClick to view 3D structurecGMP-dependent 3',5'-cyclic phosphodiesteraseO00408HumansPredicted (SEA)32.2296
Adenosine receptor A1 structureClick to view 3D structureAdenosine receptor A1P30542HumansPredicted (SEA)137.015
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)156.944
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)458.065
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)496.367
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)263.52
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)1294.63
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)245.069
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)316.924
3',5'-cyclic-AMP phosphodiesterase 4A structureClick to view 3D structure3',5'-cyclic-AMP phosphodiesterase 4AP27815HumansPredicted (SEA)25.4567
Histone deacetylase 2 structureClick to view 3D structureHistone deacetylase 2Q92769HumansPredicted (SEA)409.487
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A structureClick to view 3D structurecGMP-inhibited 3',5'-cyclic phosphodiesterase 3AQ14432HumansPredicted (SEA)37.4455
3',5'-cyclic-AMP phosphodiesterase 4B structureClick to view 3D structure3',5'-cyclic-AMP phosphodiesterase 4BQ07343HumansPredicted (SEA)66.4054
Click to view 3D structureDual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AP54750HumansPredicted (SEA)12.4559
Click to view 3D structureCone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'P16586Bos taurusPredicted (SEA)1.32344
cGMP-specific 3',5'-cyclic phosphodiesterase structureClick to view 3D structurecGMP-specific 3',5'-cyclic phosphodiesteraseO76074HumansPredicted (SEA)8.01847
ATP-binding cassette sub-family C member 5 structureClick to view 3D structureATP-binding cassette sub-family C member 5O15440HumansPredicted (SEA)1.24559
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A structureClick to view 3D structureHigh affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9AO76083HumansPredicted (SEA)9.809
Concentrations
Not Available
External Links
DrugBank IDDB00862
HMDB IDHMDB0015000
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkVardenafil
Chemspider ID99300
ChEBI ID46295
PubChem Compound ID110634
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19949666
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19959201
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20859794
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20925442
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21209618
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21235726
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21290241
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21427994
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21496853
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21548209
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21552528
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21771280
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=21883954
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=21943935
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=21950284