ACALABRUTINIB

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
UNII I42748ELQW

Structure

InChI Key WDENQIQQYWYTPO-IBGZPJMESA-N
Smiles CC#CC(=O)N1CCC[C@H]1c1nc(-c2ccc(C(=O)Nc3ccccn3)cc2)c2c(N)nccn12
InChI
InChI=1S/C26H23N7O2/c1-2-6-21(34)32-15-5-7-19(32)25-31-22(23-24(27)29-14-16-33(23)25)17-9-11-18(12-10-17)26(35)30-20-8-3-4-13-28-20/h3-4,8-14,16,19H,5,7,15H2,1H3,(H2,27,29)(H,28,30,35)/t19-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C26H23N7O2
Molecular Weight 465.52
AlogP 3.31
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 4.0
Polar Surface Area 118.51
Molecular species NEUTRAL
Aromatic Rings 4.0
Heavy Atoms 35.0

Bioactivity

Mechanism of Action Action Reference
Tyrosine-protein kinase BTK inhibitor INHIBITOR FDA
Protein: Tyrosine-protein kinase BTK
Description: Tyrosine-protein kinase BTK
Organism : Homo sapiens
Q06187 ENSG00000010671
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Adhesion
- 1210 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Alk family
- - - - 2
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase EGFR family
- 1000 140 -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakA family
- - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakB family
- - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Src family
- - - - 16
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Tec family
- 3-747 14 - 100
Membrane receptor
- 1210 - - -
Assay Description Organism Bioactivity Reference
Inhibition of recombinant BTK (unknown origin) preincubated for 1 hr followed by ATP addition by IMAP assay Homo sapiens 3.1 nM
Inhibition of recombinant human cytoplasmic His-tagged ERBB2 expressed in baculovirus at 1 uM by Z'-LYTE assay Homo sapiens 36.0 %
Inhibition of BTK in human whole blood-derived CD19+ B cells assessed as suppression of anti-IgM stimulated-CD69 expression preincubated for 1 hr followed by IgM stimulation for 18 hrs by FACS analysis Homo sapiens 198.0 nM
Inhibition of recombinant human full length His-tagged BTK expressed in baculovirus at 1 uM by Z'-LYTE assay Homo sapiens 100.0 %
Inhibition of cytoplasmic recombinant human full length His-tagged BMX expressed in baculovirus at 1 uM by Z'-LYTE assay Homo sapiens 77.0 %
Inhibition of human full length GST-tagged TXK expressed in baculovirus at 1 uM by Z'-LYTE assay Homo sapiens 31.0 %
Inhibition of recombinant human full length His-tagged BLK expressed in baculovirus at 1 uM by Z'-LYTE assay Homo sapiens 16.0 %
Inhibition of recombinant human catalytic GST-tagged JAK3 expressed in baculovirus at 1 uM by Z'-LYTE assay Homo sapiens -3.0 %
Inhibition of recombinant human cytoplasmic GST-tagged EGFR expressed in baculovirus at 1 uM by Z'-LYTE assay Homo sapiens -1.0 %
Inhibition of recombinant human cytoplasmic GST-tagged LTK expressed in baculovirus at 1 uM by Z'-LYTE assay Homo sapiens 2.0 %
Inhibition of recombinant human cytoplasmic GST-tagged ERBB4 expressed in baculovirus at 1 uM by Z'-LYTE assay Homo sapiens 93.0 %
Inhibition of recombinant human cytoplasmic full length His-tagged TEC expressed in baculovirus at 1 uM by Z'-LYTE assay Homo sapiens 71.0 %
Inhibition of BTK in human whole blood derived-basophils assessed as suppression of IgE mediated-FcepsilonR ligation-stimulated CD63 expression Homo sapiens 296.9 nM
Inhibition of BTK (unknown origin) Homo sapiens 3.0 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 13.31 %
Inhibition of BTK (unknown origin) Homo sapiens 3.0 nM
Inhibition of full-length human recombinant BTK using FITC-Ahx-TSELKKVVALYDYMPMNAND-NH2 as substrate measured after 60 mins by caliper assay Homo sapiens 19.0 nM
Inhibition of BTK in vitamin D3 differentiated human THP1 cells assessed as inhibition of FCgammaR-induced IL8 production measured after 24 hrs by HTRF assay Homo sapiens 24.0 nM
Inhibition of BTK in human B cells assessed as reduction in anti-IgM/IL4-stimulated CD69 expression on B cells preincubated for 60 mins followed by anti-IgM antibody/IL4 stimulation and measured after 16 hrs by flow cytometry Homo sapiens 203.0 nM
Binding affinity to DNA-tagged recombinant BTK (unknown origin) measured after 1 hr by biotinylated-ligand affinity bead-based qPCR analysis Homo sapiens 21.0 nM
Binding affinity to DNA-tagged recombinant BMX (unknown origin) measured after 1 hr by biotinylated-ligand affinity bead-based qPCR analysis Homo sapiens 610.0 nM
Binding affinity to DNA-tagged recombinant TEC (unknown origin) measured after 1 hr by biotinylated-ligand affinity bead-based qPCR analysis Homo sapiens 14.0 nM
Binding affinity to DNA-tagged recombinant ERBB2 (unknown origin) measured after 1 hr by biotinylated-ligand affinity bead-based qPCR analysis Homo sapiens 7.4 nM
Binding affinity to DNA-tagged recombinant ERBB4 (unknown origin) measured after 1 hr by biotinylated-ligand affinity bead-based qPCR analysis Homo sapiens 140.0 nM
Inhibition of BTK in human basophils assessed as reduction in anti-IgE mouse IgG1 antibody Le2-stimulated CD63 expression on basophil preincubated for 30 mins in presence of IgE antibody B11 followed by anti-IgE mouse IgG1 antibody Le2 stimulation and measured after 15 mins by flow cytometry Homo sapiens 747.0 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 2.21 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 18.31 %
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 -0.17 % 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 -0.15 % 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 -0.15 % 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 -0.17 %
Inhibition of His-tagged recombinant human His-tagged full length BTK expressed in baculovirus expression system using Tyr01 peptide as substrate preincubated for 1 hr by Z'lyte assay Homo sapiens 3.1 nM
Inhibition of His-tagged recombinant human TEC expressed in baculovirus expression system preincubated for 1 hr by Z'lyte assay Homo sapiens 29.0 nM
Inhibition of His-tagged recombinant full length human His-tagged BMX cytoplasmic domain expressed in baculovirus expression system using tyrosine-1 peptide as substrate preincubated for 1 hr in presence of ATP by Z'-LYTE assay Homo sapiens 46.0 nM
Inhibition of recombinant human N-terminal GST-tagged TXK (260 to 527 residues) expressed in baculovirus expression system using tyrosine-6 peptide as substrate preincubated for 1 hr in presence of ATP by Z'-LYTE assay Homo sapiens 368.0 nM
Inhibition of recombinant human N-terminal GST-tagged ERBB4 catalytic domain (708 to 993 residues) expressed in baculovirus expression system using tyrosine-1 peptide as substrate preincubated for 1 hr in presence of ATP by Z'-LYTE assay Homo sapiens 16.0 nM
Inhibition of full-length N-terminal GST tagged BTK (2 to 659 residues) (unknown origin) expressed in Sf21 insect cells using NH2-ETVYSEVRK-biotin as substrate preincubated for 1 hr followed by ATP addition and measured after 2 hrs by ELISA Homo sapiens 23.5 nM
Inhibition of full-length N-terminal GST-tagged BMX (1 to 675 residues) (unknown origin) expressed in Sf21 insect cells using NH2-ETVYSEVRK-biotin as substrate preincubated for 1 hr followed by ATP addition and measured after 2 hrs by ELISA Homo sapiens 598.0 nM
Antiproliferative activity against human TMD8 cells assessed as reduction in cell viability incubated for 72 hrs by celltiter-glo assay Homo sapiens 24.0 nM
Antiproliferative activity against human REC-1 cells assessed as reduction in cell viability incubated for 72 hrs by celltiter-glo assay Homo sapiens 13.0 nM

Cross References

Resources Reference
ChEBI 167707
ChEMBL CHEMBL3707348
DrugBank DB11703
DrugCentral 5260
FDA SRS I42748ELQW
Guide to Pharmacology 8912
PubChem 71226662
SureChEMBL SCHEMBL14637368
ZINC ZINC000208774715
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