ISTRADEFYLLINE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC N04CX01
UNII 2GZ0LIK7T4
EPA CompTox DTXSID7057652

Structure

InChI Key IQVRBWUUXZMOPW-PKNBQFBNSA-N
Smiles CCn1c(=O)c2c(nc(/C=C/c3ccc(OC)c(OC)c3)n2C)n(CC)c1=O
InChI
InChI=1S/C20H24N4O4/c1-6-23-18-17(19(25)24(7-2)20(23)26)22(3)16(21-18)11-9-13-8-10-14(27-4)15(12-13)28-5/h8-12H,6-7H2,1-5H3/b11-9+

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H24N4O4
Molecular Weight 384.44
AlogP 2.12
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 6.0
Polar Surface Area 80.28
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 28.0

Bioactivity

Mechanism of Action Action Reference
Adenosine A2a receptor antagonist ANTAGONIST PubMed
Protein: Adenosine A2a receptor
Description: Adenosine receptor A2a
Organism : Homo sapiens
P29274 ENSG00000128271
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 13000 - - -
Enzyme Oxidoreductase
- - - 27 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Adenosine receptor
- 5248-5250 1259 2-200 47
Assay Description Organism Bioactivity Reference
Displacement of [3H]CHA from Adenosine A1 receptor of rat forebrain membranes (shielded from light) Rattus norvegicus 150.0 nM
Displacement of [3H]CHA from Adenosine A1 receptor of rat forebrain membranes Rattus norvegicus 580.0 nM
Displacement of [3H]-CGS- 21680 from Adenosine A2a receptor of rat forebrain membranes (shielded from light) Rattus norvegicus 2.2 nM
In vitro binding affinity against Adenosine A2a receptor in rat forebrain membranes by [3H]NECA (+CPA) displacement. None 13.0 nM
Binding affinity towards human Adenosine A2a receptor expressed in HEK293 cells using 6 nM [3H]CGS-21680 Homo sapiens 2.2 nM
Displacement of [3H]CCPA from adenosine A1 receptor in rat brain cortical membrane Rattus norvegicus 230.0 nM
Displacement of [3H]MSX2 from adenosine A2A receptor in rat brain striatal membrane Rattus norvegicus 5.015 nM
Displacement of [3H]CCPA from adenosine A1 receptor in rat brain cortical membrane Rattus norvegicus 230.0 nM
Displacement of [3H]MSX2 from adenosine A2A receptor in rat striatal membrane Rattus norvegicus 5.15 nM
Displacement of [3H]ZM-241385 from human recombinant adenosine A2A receptor expressed in HEK293 cells Homo sapiens 6.0 nM
Displacement of [3H]ZM241385 from rat recombinant adenosine A2A receptor expressed in CHO cells Rattus norvegicus 2.0 nM
Displacement of [3H]NECA from Sprague-Dawley rat adenosine A2A receptor by scintillation counting Rattus norvegicus 4.46 nM
Displacement of [3H]CGS21680 from human adenosine A2A receptor Homo sapiens 36.0 nM
Displacement of [3H]ZM241385 from human adenosine A2A receptor expressed in buculovirus system by liquid scintillation counting Homo sapiens 72.0 nM
Displacement of [3H]-ZM241385 from human adenosine A2A receptor expressed in high five cells after 30 mins by scintillation counting Homo sapiens 72.0 nM
Displacement of [3H]ZM241385 from stabilized human adenosine receptor A2a expressed in HEK293 cells followed by receptor capturing on Biocore chips by SPR method Homo sapiens 199.53 nM
Displacement of [3H]MSX-2 from adenosine A2A receptor in rat brain striatal membrane Rattus norvegicus 5.15 nM
Displacement of [3H]CCPA from adenosine A1 receptor in rat brain cortical membrane Rattus norvegicus 230.0 nM
Displacement of [3H]PSB-298 from human recombinant adenosine A2B receptor expressed in CHO cells at 10 uM Homo sapiens 47.0 %
Displacement of [3H]MSX-2 from human recombinant adenosine A2A receptor expressed in CHO cells Homo sapiens 90.8 nM
Displacement of [3H]ZM241385 from human adenosine A2A receptor expressed in HEK293 cells after 1 hr by microbeta scintillation counting analysis Homo sapiens 47.4 nM
Antagonist activity at human adenosine A2A receptor assessed as cAMP level by cell based assay Homo sapiens 12.0 nM
Antagonist activity at human adenosine A1 receptor assessed as cAMP level by cell based assay Homo sapiens 841.0 nM
Displacement of [3H]MSX2 from adenosine A2A receptor in rat brain striatal membranes Rattus norvegicus 2.2 nM
Displacement of [3H]MSX2 from human recombinant adenosine A2A receptor expressed in CHO cells Homo sapiens 36.0 nM
Displacement of [3H]MSX2 from human recombinant adenosine A2A receptor expressed in CHO cells after 30 mins by liquid scintillation counting analysis Homo sapiens 91.2 nM
Displacement of [3H]CCPA from human recombinant adenosine A1 receptor expressed in CHO cells after 90 mins by liquid scintillation counting analysis Homo sapiens 841.0 nM
Displacement of [3H]CCPA from adenosine A1 receptor in rat brain cortical membranes after 90 mins by liquid scintillation counting analysis Rattus norvegicus 230.0 nM
Displacement of [3H]DPCPX from human adenosine A1 receptor expressed in CHO cells after 60 mins by scintillation counting analysis Homo sapiens 841.0 nM
Displacement of [3H]DPCPX from adenosine A1 receptor in rat brain after 60 mins by scintillation counting analysis Rattus norvegicus 230.0 nM
Displacement of [3H]CGS21680 from human adenosine A2A receptor expressed in CHO cells after 60 mins by scintillation counting analysis Homo sapiens 12.0 nM
Displacement of [3H]CGS21680 from adenosine A2A receptor in rat brain after 60 mins by scintillation counting analysis Rattus norvegicus 4.46 nM
Inhibition of human recombinant adenosine receptor A2a Homo sapiens 12.0 nM
Antagonist activity at adenosine A2A receptor in 5-HT-treated Wistar rat femoral vein assessed as inhibition of 2-octyn-1-yladenosine-induced vasodilation incubated for 10 mins prior to addition of 5-HT Rattus norvegicus 228.0 nM
Antagonist activity at human adenosine A2A receptor Homo sapiens 72.0 nM
Displacement of [3H]-DPCPX from Adenosine A1 receptor in Lister hooded rat brain membranes Rattus norvegicus 230.0 nM
Displacement of [3H]-ZM241385 from Adenosine A2A receptor in Lister hooded rat brain membranes Rattus norvegicus 2.2 nM
Antagonist activity at adenosine A2A receptor (unknown origin) Homo sapiens 12.0 nM
Binding affinity to human adenosine A1 receptor by radioligand displacement assay Homo sapiens 841.0 nM
Binding affinity to human adenosine A2A receptor by radioligand displacement assay Homo sapiens 12.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -0.25 %
Inhibition of human MAOB Homo sapiens 27.0 nM
Displacement of [3H]CCPA from recombinant human adenosine A1 receptor expressed in CHO cells Homo sapiens 841.0 nM
Displacement of [3H]CCPA from adenosine A1 receptor in rat brain cortical membranes Rattus norvegicus 230.0 nM
Displacement of [3H]MSX2 from recombinant human adenosine A2a receptor expressed in HEK293 cells Homo sapiens 91.2 nM
Displacement of [3H]CCPA from rat adenosine A2a receptor Rattus norvegicus 4.4 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 5.647 %
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 0.09 % 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 0.09 %
Antagonist activity at human adenosine 2A receptor Homo sapiens 36.0 nM

Cross References

Resources Reference
ChEBI 134726
ChEMBL CHEMBL431770
DrugBank DB11757
DrugCentral 4882
FDA SRS 2GZ0LIK7T4
Guide to Pharmacology 5608
PubChem 5311037
SureChEMBL SCHEMBL633262
ZINC ZINC000003803921
CONTENTS