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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL192
CHEMBL192
Compound Name SILDENAFIL
ChEMBL Synonyms VIZARSIN | REVATIO | UK-92480 | SILDENAFIL CITRATE | NIPATRA | UK-92480-10 | SILDENAFIL | UK-92,480-10 | VIAGRA
Max Phase 4 (Approved)
Trade Names REVATIO | VIZARSIN | SILDENAFIL CITRATE | NIPATRA | VIAGRA
Molecular Formula C22H30N6O4S

Additional synonyms for CHEMBL192 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
Standard InChI InChI=1S/C22H30N6O4S/c1-5-7-17-19-20(27(4)25-17)22(29)24-21( ...
Download InChI
Standard InChI Key BNRNXUUZRGQAQC-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Curated Drug Metabolism Pathways
  • Curated Drug Pharmacokinetic Data
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL192

Molecule Features

CHEMBL192 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
Arterial Occlusive DiseasesD0011573ClinicalTrials
Skin DiseasesD012871EFO:0000701skin disease0ClinicalTrials
Cystic FibrosisD003550Orphanet:586Cystic fibrosis2ClinicalTrials
HypertensionD006973EFO:0000537hypertension3ClinicalTrials
ClinicalTrials
LymphangiomaD008202EFO:1001026lymphangioendothelioma1ClinicalTrials
Meniere DiseaseD008575EFO:0006862Meniere disease2ClinicalTrials
Migraine with AuraD020325EFO:0005295migraine with aura0ClinicalTrials
Prostatic HyperplasiaD011470EFO:0000284benign prostatic hyperplasia2ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme2ClinicalTrials
Wilms TumorD009396Orphanet:654Nephroblastoma1ClinicalTrials
Acute Kidney InjuryD058186HP:0001919Acute kidney injury1ClinicalTrials
Heart FailureD006333EFO:0000373congestive heart failure3ClinicalTrials
Hepatic EncephalopathyD0065011ClinicalTrials
Idiopathic Pulmonary FibrosisD054990EFO:0000768idiopathic pulmonary fibrosis3ClinicalTrials
Liver CirrhosisD008103EFO:0001422cirrhosis of liver1ClinicalTrials
Lung DiseasesD008171EFO:0003818lung disease3ClinicalTrials
Muscular Dystrophy, DuchenneD020388Orphanet:98896Duchenne muscular dystrophy2ClinicalTrials
Peripheral Arterial DiseaseD058729EFO:0004265peripheral arterial disease2ClinicalTrials
Persistent Fetal Circulation SyndromeD010547EFO:1001103persistent fetal circulation syndrome3ClinicalTrials
DysmenorrheaD0044121ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm1ClinicalTrials
ObesityD009765EFO:0001073obesity2ClinicalTrials
StrokeD020521EFO:0000712stroke1ClinicalTrials
Anemia, Sickle CellD000755Orphanet:232Sickle cell anemia2ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma2ClinicalTrials
Diabetes MellitusD003920EFO:0000400diabetes mellitus3ClinicalTrials
Fetal Growth RetardationD005317EFO:0000495fetal growth restriction3ClinicalTrials
ClinicalTrials
Heart DiseasesD006331EFO:0003777heart disease1ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome1ClinicalTrials
Parkinson DiseaseD010300EFO:0002508Parkinson's disease2ClinicalTrials
Pre-EclampsiaD011225EFO:0000668preeclampsia2ClinicalTrials
ClinicalTrials
Pulmonary EdemaD011654EFO:1001134pulmonary edema0ClinicalTrials
Wounds and InjuriesD014947EFO:0000546injury2ClinicalTrials
Hand-Foot SyndromeD060831EFO:1001893Hand-foot syndrome1ClinicalTrials
Waldenstrom MacroglobulinemiaD008258EFO:0002616macroglobulinemia2ClinicalTrials
Hepatitis CD006526EFO:0003047hepatitis C infection1ClinicalTrials
ClinicalTrials
Premature BirthD047928EFO:0003917premature birth2ClinicalTrials
Pulmonary EmbolismD011655EFO:0003827pulmonary embolism1ClinicalTrials
Scleroderma, SystemicD012595EFO:0000717systemic scleroderma3ClinicalTrials
Skin UlcerD012883HP:0200042Skin ulcer2ClinicalTrials
Familial Primary Pulmonary HypertensionD065627Orphanet:422Idiopathic and/or familial pulmonary arterial hypertension4DailyMed
DailyMed
Macular DegenerationD008268EFO:0001365age-related macular degeneration2ClinicalTrials
Muscular Dystrophy, DuchenneD020388Orphanet:98895Becker muscular dystrophy2ClinicalTrials
Sexual Dysfunction, PhysiologicalD012735EFO:0004714sexual dysfunction2ClinicalTrials
Urinary IncontinenceD014549HP:0000020Urinary incontinence1ClinicalTrials
Venous ThrombosisD020246HP:0004936Venous thrombosis0ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
Bronchopulmonary DysplasiaD001997Orphanet:70589Bronchopulmonary dysplasia2ClinicalTrials
Coronary VasospasmD003329EFO:0004225Coronary Vasospasm3ClinicalTrials
Erectile DysfunctionD007172EFO:0004234erectile dysfunction3ClinicalTrials
ClinicalTrials
Heart FailureD006333EFO:0003144heart failure3ClinicalTrials
ClinicalTrials
Hypertension, PulmonaryD006976EFO:0001361pulmonary hypertension3ClinicalTrials
ClinicalTrials
InfertilityD007246EFO:0000545infertility2ClinicalTrials
ClinicalTrials
Raynaud DiseaseD011928EFO:1001145Raynaud disease2ClinicalTrials

Clinical Data

ClinicalTrials.gov SILDENAFIL
The Cochrane Collaboration SILDENAFIL

Metabolites for CHEMBL192

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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 CHEMBL192. 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 CHEMBL192. 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
G04BE03 - sildenafil

ChemSpider ChemSpider:BNRNXUUZRGQAQC-UHFFFAOYSA-N
DailyMed sildenafil citrate
PubChem SID: 26748898 SID: 50085897

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL192



ACToR 139755-83-2
BindingDB 14390
Brenda 615 117589
ChEBI 9139
ChemicalBook CB2747316
DrugBank DB00203
DrugCentral 2441
eMolecules 902463
EPA CompTox Dashboard DTXSID6023579
FDA SRS 3M7OB98Y7H
Guide to Pharmacology 4743
Human Metabolome Database HMDB0005039
IBM Patent System B4C8D37088229EEF1898CF32611BFC03 D814FFE26EDA163F0CDC1115AD9C7CC3
KEGG Ligand C07259
LINCS LSM-3797
Mcule MCULE-2481702478
MolPort MolPort-002-885-861
Nikkaji J897.167F
PDBe VIA
PharmGKB PA451346
PubChem 5212
PubChem: Thomson Pharma 14883184 14834479
SureChEMBL SCHEMBL1895
ZINC ZINC000019796168

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