TADALAFIL

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC G04BE08
UNII 742SXX0ICT
EPA CompTox DTXSID9046786

Structure

InChI Key WOXKDUGGOYFFRN-IIBYNOLFSA-N
Smiles CN1CC(=O)N2[C@H](c3ccc4c(c3)OCO4)c3[nH]c4ccccc4c3C[C@@H]2C1=O
InChI
InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H19N3O4
Molecular Weight 389.41
AlogP 2.21
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 1.0
Polar Surface Area 74.87
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 29.0

Bioactivity

Mechanism of Action Action Reference
Phosphodiesterase 5A inhibitor INHIBITOR DailyMed
Protein: Phosphodiesterase 5A
Description: cGMP-specific 3',5'-cyclic phosphodiesterase
Organism : Homo sapiens
O76074 ENSG00000138735
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 26159 - - -
Enzyme Phosphodiesterase Phosphodiesterase 11 Phosphodiesterase 11A
- 10-60000 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4A
- 9200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4B
- 9200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4C
- 9200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 4 Phosphodiesterase 4D
- 9200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 5 Phosphodiesterase 5A
78 1-9 - 5-10 -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6A
- 980-5200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6B
- 980-5200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6C
- 980-5200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6D
- 980-5200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6G
- 980-5200 - - -
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6H
- 980-5200 - - -
Enzyme
78 1-9 - 5-10 0
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 79433-100000 - - -
Assay Description Organism Bioactivity Reference
In vitro inhibitory activity against bovine phosphodiesterase 5 None 5.0 nM In vitro inhibitory activity against bovine phosphodiesterase 5 None 5.0 nM
Inhibitory activity against phosphodiesterase 5 (PDE5) obtained from human corpus cavernosum tissue None 6.7 nM
Inhibition of Phosphodiesterase 5 from human platelets Homo sapiens 1.3 nM
Inhibitory activity against phosphodiesterase 11 (PDE11) obtained from recombinant Sf9 expression None 37.0 nM
Effective concentration against rat aortic smooth muscle cell Rattus norvegicus 500.0 nM Effective concentration against rat aortic smooth muscle cell Rattus norvegicus 150.0 nM
Inhibition of human phosphodiesterase 5 Homo sapiens 10.0 nM
Inhibition of phosphodiesterase 5 in rat fetal lung fibroblast (RFL-6) cells Rattus norvegicus 5.0 nM
Inhibition of human phosphodiesterase 5 Homo sapiens 4.0 nM
Inhibition of human phosphodiesterase 6 Homo sapiens 980.0 nM
Inhibition of human phosphodiesterase 11 Homo sapiens 33.0 nM
Inhibition of bovine PDE5 after 24 hrs by HTRF Bos taurus 3.3 nM
Inhibition of PDE5 None 5.012 nM
Inhibition of bovine PDE5 Bos taurus 12.0 nM
Inhibition of human recombinant PDE11 Homo sapiens 290.0 nM
Inhibition of human recombinant PDE11 Homo sapiens 290.0 nM
Inhibition of bovine platelet PDE5 Bos taurus 12.0 nM
Inhibition of human recombinant PDE5 after 1.5 hrs by fluorescent polarization assay Homo sapiens 4.0 nM
Inhibition of human recombinant PDE5A-mediated hydrolysis of cGMP after 30 mins by fluorescence polarization assay Homo sapiens 3.0 nM
Inhibition of human recombinant PDE11A-mediated hydrolysis of cAMP after 30 mins by fluorescence polarization assay Homo sapiens 300.0 nM
Inhibition of human recombinant PDE11A-mediated hydrolysis of cGMP after 30 mins by fluorescence polarization assay Homo sapiens 50.0 nM
Inhibition of Trypanosoma brucei PDEB1 using cAMP as substrate at 100 uM preincubated for 10 mins prior substrate addition by spectrophotometry Trypanosoma brucei 0.0 %
Inhibition of bovine PDE5 after 24 hrs by time-resolved fluorescence resonance energy transfer assay Bos taurus 5.0 nM
Inhibition of PDE11 (unknown origin) using FAM-cGMP and FAM-cAMP as substrate after 60 mins by fluorescence assay Homo sapiens 10.0 nM
Inhibition of PDE5 (unknown origin) using FAM-cGMP as substrate after 60 mins by fluorescence assay Homo sapiens 1.2 nM
Inhibition of recombinant human PDE5A Homo sapiens 9.4 nM
Inhibition of PDE5A (unknown origin) Homo sapiens 1.2 nM
Inhibition of PDE5 (unknown origin) Homo sapiens 3.162 nM
Inhibition of PDE5A (unknown origin) Homo sapiens 9.4 nM
Inhibition of PDE5 (unknown origin) Homo sapiens 5.2 nM
Inhibition of full length recombinant human N-terminal GST-tagged PDE5A1 expressed in baculovirus infected sf9 cells using FAM-cyclic-3',5-GMP as substrate after 1 hr by fluorescence polarization assay Homo sapiens 4.67 nM
Inhibition of full length recombinant human N-terminal GST-tagged PDE11A4 expressed in baculovirus infected sf9 cells using FAM-cyclic-3',5-AMP as substrate after 1 hr by fluorescence polarization assay Homo sapiens 47.0 nM
Inhibition of PDE5 in Wistar rat mesentric arteries assessed as inhibition of phenylephrine-induced contraction by measuring increase in acetylcholine-induced vasorelaxation by pressure myographic method Rattus norvegicus 78.0 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 6.36 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 0.57 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 2.98 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 15.72 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 22.42 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans -1.32 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -3.58 %
Inhibition of PDE5A1 (unknown origin) by immobilized metal ion affinity-based fluorescence polarization Homo sapiens 4.0 nM
Inhibition of N-terminal GST-tagged human PDE5A1 expressed in baculovirus infected sf9 cells using [3H]cGMP as substrate measured after 30 mins by scintillation proximity assay Homo sapiens 2.35 nM
Inhibition of N-terminal GST-tagged human PDE6C expressed in baculovirus infected sf9 cells using [3H]cGMP as substrate measured after 30 mins by scintillation proximity assay Homo sapiens 402.0 nM
Inhibition of N-terminal GST-tagged human PDE11A4 expressed in baculovirus infected sf9 cells using [3H]cGMP as substrate measured after 30 mins by scintillation proximity assay Homo sapiens 22.1 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 12.4 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.14 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.14 %
Inhibition of PDE5A (unknown origin) Homo sapiens 5.0 nM

Cross References

Resources Reference
ChEBI 71940
ChEMBL CHEMBL779
DrugBank DB00820
DrugCentral 2553
FDA SRS 742SXX0ICT
Human Metabolome Database HMDB0014958
Guide to Pharmacology 7299
KEGG D02008
PDB CIA
PharmGKB PA10333
PubChem 110635
SureChEMBL SCHEMBL33333
ZINC ZINC000003993855
CONTENTS