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Record Information
Version2.0
Created at2024-09-10 18:54:55 UTC
Updated at2024-09-10 18:54:55 UTC
NP-MRD IDNP0334562
Secondary Accession NumbersNone
Natural Product Identification
Common NameSildenafil
DescriptionSildenafil, also known as aphrodil or caverta, 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. Sildenafil was first documented in 2000 (PMID: 10845762). Sildenafil is a very strong basic compound (based on its pKa) (PMID: 10725306) (PMID: 15797756) (PMID: 10693332) (PMID: 15213306).
Structure
Thumb
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 Mass474.5760 Da
Monoisotopic Mass474.20492 Da
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
CAS Registry NumberNot Available
SMILES
CCCC1=NN(C)C2=C1NC(=NC2=O)C1=C(OCC)C=CC(=C1)S(=O)(=O)N1CCN(C)CC1
InChI Identifier
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)
InChI KeyBNRNXUUZRGQAQC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0005039
DrugBank IDDB00203
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023606
KNApSAcK IDNot Available
Chemspider ID5023
KEGG Compound IDC07259
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSildenafil
METLIN IDNot Available
PubChem Compound5212
PDB IDNot Available
ChEBI ID9139
Good Scents IDNot Available
References
General References
  1. 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. doi: 10.1038/sj.ijir.3900504. [PubMed:10845762 ]
  2. 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. [PubMed:10725306 ]
  3. 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. doi: 10.1016/j.healun.2004.01.017. [PubMed:15797756 ]
  4. Fekete F, Fabian E: [Effectiveness and adverse effects of sildenafil in erectile dysfunction]. Orv Hetil. 2000 Jan 16;141(3):115-8. [PubMed:10693332 ]
  5. 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. doi: 10.1124/mol.66.1.144. [PubMed:15213306 ]