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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1737
CHEMBL1737
Compound Name SILDENAFIL CITRATE
ChEMBL Synonyms SILDENAFIL CITRATE | REVATIO | UK-92,480-10 | VIAGRA | UK-92480-10
Max Phase 4 (Approved)
Trade Names REVATIO | SILDENAFIL CITRATE | VIAGRA
Molecular Formula C28H38N6O11S

Additional synonyms for CHEMBL1737 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCCc1nn(C)c2C(=O)NC(=Nc12)c3cc(ccc3OCC)S(=O)(=O)N4CCN(C)CC4. ...
Download SMILES
Standard InChI InChI=1S/C22H30N6O4S.C6H8O7/c1-5-7-17-19-20(27(4)25-17)22(29 ...
Download InChI
Standard InChI Key DEIYFTQMQPDXOT-UHFFFAOYSA-N

Sources

  • Curated Drug Metabolism Pathways
  • Curated Drug Pharmacokinetic Data
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names

Alternate Forms of Compound in ChEMBL


CHEMBL1737

Molecule Features

CHEMBL1737 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:Y 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
GlioblastomaD005909EFO:0000519glioblastoma multiforme2ClinicalTrials
HypertensionD006973EFO:0000537hypertension2ClinicalTrials
ClinicalTrials
Wilms TumorD009396Orphanet:654Nephroblastoma1ClinicalTrials
DysmenorrheaD0044121ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm1ClinicalTrials
ObesityD009765EFO:0001073obesity2ClinicalTrials
StrokeD020521EFO:0000712stroke1ClinicalTrials
Fetal Growth RetardationD005317EFO:0000495fetal growth restriction3ClinicalTrials
ClinicalTrials
Hand-Foot SyndromeD060831EFO:1001893Hand-foot syndrome1ClinicalTrials
Pre-EclampsiaD011225EFO:0000668preeclampsia2ClinicalTrials
ClinicalTrials
Waldenstrom MacroglobulinemiaD008258EFO:0002616macroglobulinemia2ClinicalTrials
Familial Primary Pulmonary HypertensionD065627Orphanet:422Idiopathic and/or familial pulmonary arterial hypertension4DailyMed
DailyMed
Hepatitis CD006526EFO:0003047hepatitis C infection1ClinicalTrials
ClinicalTrials
Macular DegenerationD008268EFO:0001365age-related macular degeneration2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
Erectile DysfunctionD007172EFO:0004234erectile dysfunction3ClinicalTrials
ClinicalTrials
Heart FailureD006333EFO:0003144heart failure3ClinicalTrials
ClinicalTrials
Hypertension, PulmonaryD006976EFO:0001361pulmonary hypertension3ClinicalTrials
ClinicalTrials
InfertilityD007246EFO:0000545infertility2ClinicalTrials
ClinicalTrials

Clinical Data

ClinicalTrials.gov SILDENAFIL CITRATE
The Cochrane Collaboration SILDENAFIL CITRATE

Metabolites for CHEMBL1737

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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 CHEMBL1737. 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
CHEMBL4567 Phosphodiesterase 5A Rattus norvegicus 1.000

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1827 Phosphodiesterase 5A Homo sapiens 1.000
CHEMBL4567 Phosphodiesterase 5A Rattus norvegicus 1.000
CHEMBL2717 Phosphodiesterase 11A Homo sapiens 0.992

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
474.6 474.2049 1.61 7 113.42 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
10.05 6.03 2.47 2.45 3 33 0.55

Structural Alerts

There are 1 structural alerts for CHEMBL1737. To view alerts please click here.

Compound Cross References

ChemSpider ChemSpider:DEIYFTQMQPDXOT-UHFFFAOYSA-N
DailyMed sildenafil citrate
PubChem SID: 144205270 SID: 170465285
Wikipedia Sildenafil

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1737



ACToR 171599-83-0
Brenda 117592
ChEBI 58987
ChemicalBook CB9407725
eMolecules 32234216 2725427
EPA CompTox Dashboard DTXSID4046076
FDA SRS BW9B0ZE037
Mcule MCULE-7780487665
MolPort MolPort-006-069-375 MolPort-003-850-246 MolPort-006-823-012
PubChem 62853
PubChem: Drugs of the Future 12014701
PubChem: Thomson Pharma 14888244 16783095 14912810
Selleck Sildenafil-citrate
SureChEMBL SCHEMBL33982

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