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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1873475
CHEMBL1873475
Compound Name IBRUTINIB
ChEMBL Synonyms CRA-032765 | IMBRUVICA | IBRUTINIB | PCI-32765-00 | PCI-32765
Max Phase 4 (Approved)
Trade Names IMBRUVICA
Molecular Formula C25H24N6O2

Additional synonyms for CHEMBL1873475 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Nc1ncnc2c1c(nn2[C@@H]3CCCN(C3)C(=O)C=C)c4ccc(Oc5ccccc5)cc4
Standard InChI InChI=1S/C25H24N6O2/c1-2-21(32)30-14-6-7-18(15-30)31-25-22(2 ...
Download InChI
Standard InChI Key XYFPWWZEPKGCCK-GOSISDBHSA-N

Sources

  • AstraZeneca Deposited Data
  • BindingDB Database
  • British National Formulary
  • 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


CHEMBL1873475

Molecule Features

CHEMBL1873475 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:Y 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
Tyrosine-protein kinase BTK inhibitor Tyrosine-protein kinase BTK FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Burkitt LymphomaD002051EFO:0000309Burkitts lymphoma3ClinicalTrials
Colonic NeoplasmsD003110EFO:1001950colon carcinoma1ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma2ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
AmyloidosisD000686EFO:1001875amyloidosis2ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome1ClinicalTrials
Waldenstrom MacroglobulinemiaD008258EFO:0002616macroglobulinemia4ClinicalTrials
DailyMed
Breast NeoplasmsD001943EFO:0003869breast neoplasm1ClinicalTrials
Graft vs Host DiseaseD006086EFO:0004599acute graft vs. host disease3ClinicalTrials
MelanomaD008545EFO:0002617metastatic melanoma2ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
Carcinoid TumorD002276EFO:0004243carcinoid tumor2ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia4ClinicalTrials
DailyMed
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia2ClinicalTrials
MelanomaD008545EFO:0000389cutaneous melanoma2ClinicalTrials
Hematologic NeoplasmsD019337EFO:0001642lymphoid neoplasm1ClinicalTrials
LeukemiaD007938EFO:0000565leukemia2ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma1ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma1ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia2ClinicalTrials
Lymphoma, FollicularD008224EFO:0000096neoplasm of mature B-cells3ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma3ClinicalTrials
Lymphoma, Mantle-CellD020522EFO:1001469Mantle cell lymphoma4ClinicalTrials
DailyMed
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma3ClinicalTrials
MelanomaD008545EFO:0000756melanoma2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma1ClinicalTrials
Food HypersensitivityD005512EFO:1001890food allergy2ClinicalTrials
Leukemia, Hairy CellD007943EFO:1000956hairy cell leukemia2ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia1ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma2ClinicalTrials
Liver DiseasesD008107EFO:0001421liver disease1ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials

Clinical Data

ClinicalTrials.gov IBRUTINIB
The Cochrane Collaboration IBRUTINIB

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 CHEMBL1873475. 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
CHEMBL3234 Tyrosine-protein kinase HCK Homo sapiens 1.000
CHEMBL5251 Tyrosine-protein kinase BTK Homo sapiens 1.000
CHEMBL258 Tyrosine-protein kinase LCK Homo sapiens 1.000
CHEMBL4142 Fibroblast growth factor receptor 2 Homo sapiens 1.000
CHEMBL1841 Tyrosine-protein kinase FYN Homo sapiens 1.000
CHEMBL1781862 Calmodulin-domain protein kinase 1 Toxoplasma gondii 1.000
CHEMBL2959 Tyrosine-protein kinase ITK/TSK Homo sapiens 1.000
CHEMBL3142 DNA-dependent protein kinase Homo sapiens 1.000
CHEMBL267 Tyrosine-protein kinase SRC Homo sapiens 1.000
CHEMBL2250 Tyrosine-protein kinase BLK Homo sapiens 0.994
CHEMBL3267 PI3-kinase p110-gamma subunit Homo sapiens 0.987
CHEMBL2073 Tyrosine-protein kinase YES Homo sapiens 0.987
CHEMBL3130 PI3-kinase p110-delta subunit Homo sapiens 0.981
CHEMBL3905 Tyrosine-protein kinase Lyn Homo sapiens 0.971
CHEMBL4454 Tyrosine-protein kinase FGR Homo sapiens 0.935
CHEMBL203 Epidermal growth factor receptor erbB1 Homo sapiens 0.832
CHEMBL2041 Tyrosine-protein kinase receptor RET Homo sapiens 0.675



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL3234 Tyrosine-protein kinase HCK Homo sapiens 1.000
CHEMBL5251 Tyrosine-protein kinase BTK Homo sapiens 1.000
CHEMBL2959 Tyrosine-protein kinase ITK/TSK Homo sapiens 1.000
CHEMBL2634 Tyrosine-protein kinase CSK Homo sapiens 1.000
CHEMBL4142 Fibroblast growth factor receptor 2 Homo sapiens 1.000
CHEMBL258 Tyrosine-protein kinase LCK Homo sapiens 1.000
CHEMBL1841 Tyrosine-protein kinase FYN Homo sapiens 1.000
CHEMBL1781862 Calmodulin-domain protein kinase 1 Toxoplasma gondii 1.000
CHEMBL3268 PI4-kinase beta subunit Homo sapiens 1.000
CHEMBL267 Tyrosine-protein kinase SRC Homo sapiens 1.000
CHEMBL203 Epidermal growth factor receptor erbB1 Homo sapiens 1.000
CHEMBL3267 PI3-kinase p110-gamma subunit Homo sapiens 1.000
CHEMBL3130 PI3-kinase p110-delta subunit Homo sapiens 0.999
CHEMBL3142 DNA-dependent protein kinase Homo sapiens 0.999
CHEMBL2073 Tyrosine-protein kinase YES Homo sapiens 0.986
CHEMBL2250 Tyrosine-protein kinase BLK Homo sapiens 0.983
CHEMBL3834 Tyrosine-protein kinase BMX Homo sapiens 0.974
CHEMBL3905 Tyrosine-protein kinase Lyn Homo sapiens 0.970
CHEMBL4454 Tyrosine-protein kinase FGR Homo sapiens 0.950
CHEMBL2041 Tyrosine-protein kinase receptor RET Homo sapiens 0.914

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
440.5 440.1961 4.22 5 99.16 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
7 1 0 8 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 4.09 4.47 4.47 4 33 0.47

Structural Alerts

There are 8 structural alerts for CHEMBL1873475. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01X - OTHER ANTINEOPLASTIC AGENTS
L01XE - Protein kinase inhibitors
L01XE27 - ibrutinib

ChemSpider ChemSpider:XYFPWWZEPKGCCK-GOSISDBHSA-N
DailyMed ibrutinib
PubChem SID: 124898784

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1873475



BindingDB 50357312
Brenda 213563
ChEBI 76612
ChemicalBook CB12515873
DrugBank DB09053
DrugCentral 4810
EPA CompTox Dashboard DTXSID60893450
FDA SRS 1X70OSD4VX
Guide to Pharmacology 6912
IBM Patent System B961AFA590EB4C0EDA4CED0A068FACA6
LINCS LSM-45830
MolPort MolPort-027-806-955
Nikkaji J2.980.554G
PDBe 1E8
PharmGKB PA166121346
PubChem 24821094
PubChem: Thomson Pharma 49837088
SureChEMBL SCHEMBL201859
ZINC ZINC000035328014

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