Vardenafil (CHEM022191)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:23:17 UTC
Update Date2016-11-09 01:17:26 UTC
Accession NumberCHEM022191
Identification
Common NameVardenafil
ClassSmall Molecule
DescriptionVardenafil (Levitra) is an oral therapy for the treatment of erectile dysfunction. It is a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5). Penile erection is a hemodynamic process initiated by the relaxation of smooth muscle in the corpus cavernosum and its associated arterioles. During sexual stimulation, nitric oxide is released from nerve endings and endothelial cells in the corpus cavernosum. Nitric oxide activates the enzyme guanylate cyclase resulting in increased synthesis of cyclic guanosine monophosphate (cGMP) in the smooth muscle cells of the corpus cavernosum. The cGMP in turn triggers smooth muscle relaxation, allowing increased blood flow into the penis, resulting in erection. The tissue concentration of cGMP is regulated by both the rates of synthesis and degradation via phosphodiesterases (PDEs). The most abundant PDE in the human corpus cavernosum is the cGMPspecific phosphodiesterase type 5 (PDE5); therefore, the inhibition of PDE5 enhances erectile function by increasing the amount of cGMP.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9304600000-78a6e2bde8e38b367f38Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0040900000-a78a646244f2fb1f6276Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000f-0011900000-88f62b9a8f7aec917a41Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0092000000-cf98ecae287c01370dbcSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-052r-0000900000-9008f3921907d4675261Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-1fcc6df6cdb6126d7ef0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-055r-0091200000-d63a9cf854a198162e08Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-93d391256ac331406facSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1924200000-417e1644b94601dd7f35Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000900000-b883d879992fbedff256Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090200000-050ed3eecf1ffddad8e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-014i-0925000000-41aba03d13dfc7df8fafSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-0413900000-e1526827ae9f58ddf244Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-052r-0000900000-e5ff9d0dc7199d2f0c84Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-e10263c8f866f8b725eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-3100900000-665b3066495254822a6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0000900000-3b1c3b5e3ebaf21ef591Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000900000-99f18e7a2ea26f21682bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-055r-0091200000-74cac0a8c4e6f18b2567Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000900000-7205fafb37f359d4065dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0002900000-c0cecdb93e99efbd369eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01w0-3536900000-89e4ca7c7d6e6e2e281eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ai-5492100000-78d239c94528460e3603Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-caa7e887e43db6fbbc44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0570-0412900000-c93873d3bd3336545c26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-3900000000-b864d4adedbfa7b24b3bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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