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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1520
CHEMBL1520
Compound Name VARDENAFIL
ChEMBL Synonyms VARDENAFIL DIHYDROCHLORIDE | LEVITRA | STAXYN | VARDENAFIL HYDROCHLORIDE | VARDENAFIL
Max Phase 4 (Approved)
Trade Names VARDENAFIL HYDROCHLORIDE | LEVITRA | STAXYN
Molecular Formula C23H32N6O4S

Additional synonyms for CHEMBL1520 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCCc1nc(C)c2C(=O)N=C(Nn12)c3cc(ccc3OCC)S(=O)(=O)N4CCN(CC)CC4
Standard InChI InChI=1S/C23H32N6O4S/c1-5-8-20-24-16(4)21-23(30)25-22(26-29( ...
Download InChI
Standard InChI Key SECKRCOLJRRGGV-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Curated Drug Pharmacokinetic Data
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1520

Molecule Features

CHEMBL1520 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Phosphodiesterase 5A inhibitor Phosphodiesterase 5A DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Cystic FibrosisD003550Orphanet:586Cystic fibrosis2ClinicalTrials
Urinary Bladder, OveractiveD053201EFO:1000781overactive bladder2ClinicalTrials
Erectile DysfunctionD007172EFO:0004234erectile dysfunction3ClinicalTrials
Reperfusion InjuryD015427EFO:0002687ischemia reperfusion injury1ClinicalTrials
Prostatic HyperplasiaD011470EFO:0000284benign prostatic hyperplasia2ClinicalTrials
Raynaud DiseaseD011928EFO:1001145Raynaud disease2ClinicalTrials
TinnitusD0140122ClinicalTrials
Hypertension, PulmonaryD006976EFO:0001361pulmonary hypertension3ClinicalTrials

Clinical Data

ClinicalTrials.gov VARDENAFIL
The Cochrane Collaboration VARDENAFIL

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1520. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1827 Phosphodiesterase 5A Homo sapiens 1.000
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.909
CHEMBL1947 Thyroid hormone receptor beta-1 Homo sapiens 0.892
CHEMBL1075189 Pyruvate kinase isozymes M1/M2 Homo sapiens 0.759
CHEMBL4096 Cellular tumor antigen p53 Homo sapiens 0.696

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1827 Phosphodiesterase 5A Homo sapiens 1.000
CHEMBL2717 Phosphodiesterase 11A Homo sapiens 0.987
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.846
CHEMBL1947 Thyroid hormone receptor beta-1 Homo sapiens 0.797
CHEMBL1075189 Pyruvate kinase isozymes M1/M2 Homo sapiens 0.689
CHEMBL4096 Cellular tumor antigen p53 Homo sapiens 0.364
CHEMBL1293299 Histone-lysine N-methyltransferase MLL Homo sapiens 0.247

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
488.6 488.2206 2.07 8 112.9 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
8 1 0 10 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 7.13 3.64 3.45 3 34 0.52

Structural Alerts

There are 1 structural alerts for CHEMBL1520. To view alerts please click here.

Compound Cross References

ATC G - GENITO URINARY SYSTEM AND SEX HORMONES
G04 - UROLOGICALS
G04B - UROLOGICALS
G04BE - Drugs used in erectile dysfunction
G04BE09 - vardenafil

ChemSpider ChemSpider:SECKRCOLJRRGGV-UHFFFAOYSA-N
DailyMed vardenafil hydrochloride
Wikipedia Vardenafil

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1520



ACToR 224785-90-4
BindingDB 50088373 14776
Brenda 1227 70659 117594
ChEBI 46295
DrugBank DB00862
DrugCentral 2809
eMolecules 30390394 36366753 36516854
EPA CompTox Dashboard DTXSID3048318
FDA SRS UCE6F4125H
Guide to Pharmacology 7320
Human Metabolome Database HMDB0015000
IBM Patent System DA314CC32AF311691A49AE3D5289A9D4
LINCS LSM-2292
Mcule MCULE-5211071344
MolPort MolPort-005-975-775 MolPort-002-672-272
Nikkaji J1.662.658I
PDBe VDN
PharmGKB PA10229
PubChem 110634
PubChem: Thomson Pharma 14785997 14932815
SureChEMBL SCHEMBL5772
ZINC ZINC000018324776

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/SECKRCOLJRRGGV-UHFFFAOYSA-N spacer
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