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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL779
CHEMBL779
Compound Name TADALAFIL
ChEMBL Synonyms TADALAFIL | CIALIS | IC-351 | ADCIRCA | IC351
Max Phase 4 (Approved)
Trade Names CIALIS | ADCIRCA
Molecular Formula C22H19N3O4

Additional synonyms for CHEMBL779 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN1CC(=O)N2[C@H](Cc3c([nH]c4ccccc34)[C@H]2c5ccc6OCOc6c5)C1=O
Standard InChI InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4- ...
Download InChI
Standard InChI Key WOXKDUGGOYFFRN-IIBYNOLFSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Drugs for Neglected Diseases Initiative (DNDi)
  • 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


CHEMBL779

Molecule Features

CHEMBL779 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer 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
Anemia, Sickle CellD000755Orphanet:232Sickle cell anemia2ClinicalTrials
Lung Diseases, InterstitialD017563EFO:0004244interstitial lung disease3ClinicalTrials
Muscular Dystrophy, DuchenneD020388Orphanet:98896Duchenne muscular dystrophy3ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000181head and neck squamous cell carcinoma2ClinicalTrials
Erectile DysfunctionD007172EFO:0004234erectile dysfunction3ClinicalTrials
StrokeD020521EFO:0000712stroke2ClinicalTrials
GastroparesisD018589EFO:1000948gastroparesis2ClinicalTrials
Heart FailureD006333EFO:0000373congestive heart failure1ClinicalTrials
HypertensionD006973EFO:0000537hypertension2ClinicalTrials
Muscular DystrophiesD009136Orphanet:98473Muscular dystrophy0ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0004284upper aerodigestive tract neoplasm0ClinicalTrials
Heart Defects, CongenitalD0063303ClinicalTrials
Essential HypertensionD000075222EFO:1002032primary hypertension2ClinicalTrials
Hypertension, PulmonaryD006976EFO:0001361pulmonary hypertension3ClinicalTrials
NeoplasmsD009369EFO:0000311cancer1ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm1ClinicalTrials
Prostatic HyperplasiaD011470EFO:0000284benign prostatic hyperplasia3ClinicalTrials
Dementia, VascularD015140EFO:0004718vascular dementia2ClinicalTrials
Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus2ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials
ObesityD009765EFO:0001073obesity2ClinicalTrials
Raynaud DiseaseD011928EFO:1001145Raynaud disease3ClinicalTrials
Scleroderma, SystemicD012595EFO:0000717systemic scleroderma2ClinicalTrials
Cushing SyndromeD003480EFO:0003099Cushing syndrome2ClinicalTrials

Clinical Data

ClinicalTrials.gov TADALAFIL
The Cochrane Collaboration TADALAFIL

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 CHEMBL779. 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
CHEMBL3478 Phosphodiesterase 5A Bos taurus 1.000
CHEMBL2717 Phosphodiesterase 11A Homo sapiens 1.000
CHEMBL2331047 Sodium/iodide cotransporter Rattus norvegicus 1.000
CHEMBL4567 Phosphodiesterase 5A Rattus norvegicus 1.000
CHEMBL1833 Serotonin 2b (5-HT2b) receptor Homo sapiens 1.000
CHEMBL1942 Alpha-2b adrenergic receptor Homo sapiens 0.997
CHEMBL4581 Kinesin-like protein 1 Homo sapiens 0.991
CHEMBL313 Serotonin transporter Rattus norvegicus 0.978
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.842
CHEMBL2238 Somatostatin receptor 3 Mus musculus 0.520
CHEMBL1075280 Dual specificity protein kinase CLK1 Mus musculus 0.492
CHEMBL240 HERG Homo sapiens 0.458
CHEMBL3949 Endothelin receptor ET-B Sus scrofa 0.422
CHEMBL273 Serotonin 1a (5-HT1a) receptor Rattus norvegicus 0.296
CHEMBL340 Cytochrome P450 3A4 Homo sapiens 0.216
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.213
CHEMBL214 Serotonin 1a (5-HT1a) receptor Homo sapiens 0.212



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1827 Phosphodiesterase 5A Homo sapiens 1.000
CHEMBL3478 Phosphodiesterase 5A Bos taurus 1.000
CHEMBL2717 Phosphodiesterase 11A Homo sapiens 1.000
CHEMBL2331047 Sodium/iodide cotransporter Rattus norvegicus 1.000
CHEMBL4567 Phosphodiesterase 5A Rattus norvegicus 0.996
CHEMBL1833 Serotonin 2b (5-HT2b) receptor Homo sapiens 0.989
CHEMBL4581 Kinesin-like protein 1 Homo sapiens 0.970
CHEMBL1942 Alpha-2b adrenergic receptor Homo sapiens 0.906
CHEMBL313 Serotonin transporter Rattus norvegicus 0.877
CHEMBL1075280 Dual specificity protein kinase CLK1 Mus musculus 0.864
CHEMBL2903 Arachidonate 15-lipoxygenase Homo sapiens 0.797
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.762
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.531
CHEMBL340 Cytochrome P450 3A4 Homo sapiens 0.415
CHEMBL1916 Alpha-2c adrenergic receptor Homo sapiens 0.323
CHEMBL2238 Somatostatin receptor 3 Mus musculus 0.286
CHEMBL273 Serotonin 1a (5-HT1a) receptor Rattus norvegicus 0.208

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
389.4 389.1376 2.21 1 74.87 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 1 0 7 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- - 2.71 2.71 3 29 0.69

Structural Alerts

There are no structural alerts for CHEMBL779

Compound Cross References

ATC G - GENITO URINARY SYSTEM AND SEX HORMONES
G04 - UROLOGICALS
G04B - UROLOGICALS
G04BE - Drugs used in erectile dysfunction
G04BE08 - tadalafil

ChemSpider ChemSpider:WOXKDUGGOYFFRN-IIBYNOLFSA-N
DailyMed tadalafil
PubChem SID: 144206195 SID: 170464819 SID: 26719828 SID: 49666420
Wikipedia Tadalafil

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL779



ACToR 171596-29-5
BindingDB 14777
Brenda 1339
ChEBI 71940
ChemicalBook CB2236841
DrugBank DB00820
DrugCentral 2553
eMolecules 29781353 33507691 36754634
EPA CompTox Dashboard DTXSID9046786
FDA SRS 742SXX0ICT
Guide to Pharmacology 7299
Human Metabolome Database HMDB0014958
IBM Patent System 0A7EDA98D19B313BFCBE165E80446000
LINCS LSM-4109
MolPort MolPort-002-885-864
NIH Clinical Collection SAM001246586
Nikkaji J1.662.659G
PDBe CIA
PharmGKB PA10333
PubChem 110635
PubChem: Drugs of the Future 12015128
PubChem: Thomson Pharma 14805118 14756405
Selleck Tadalafil(Cialis)
SureChEMBL SCHEMBL33333
ZINC ZINC000003993855

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