IBRUTINIB

Search structure
Trade Names:
Synonyms:
Status: Approved (2013)
Entry Type: Small molecule
Molecule Category: UNKNOWN
UNII: 1X70OSD4VX

Structure
InChI Key XYFPWWZEPKGCCK-GOSISDBHSA-N
Smile C=CC(=O)N1CCC[C@@H](n2nc(-c3ccc(Oc4ccccc4)cc3)c3c(N)ncnc32)C1
InChI
InChI=1S/C25H24N6O2/c1-2-21(32)30-14-6-7-18(15-30)31-25-22(24(26)27-16-28-25)23(29-31)17-10-12-20(13-11-17)33-19-8-4-3-5-9-19/h2-5,8-13,16,18H,1,6-7,14-15H2,(H2,26,27,28)/t18-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C25H24N6O2
Molecular Weight 440.51
AlogP 4.22
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 99.16
Molecular species NEUTRAL
Aromatic Rings 4.0
Heavy Atoms 33.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Tyrosine-protein kinase BTK inhibitor FDA
Primary Target
Bruton tyrosine kinase
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Adhesion
- 120 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2B Cytochrome P450 2B6
- 11100 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 19000-33500 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C8
- 7900 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 8500-9690 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 11000-40800 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Alk family
- - - - 81
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Csk family
- 2 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase EGFR family
49 1-390 1 - 89
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakA family
- 10-146 37 - 80
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakB family
- 10-146 37 - 80
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase PDGFR family
- 5545 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Ret family
- 5-37 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Src family
- 0-1 - - 102
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Tec family
- 0-10350 2 5-425 99-101
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 1100-7700 - 1100 1
Membrane receptor
- 120 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 4 Nuclear hormone receptor subfamily 4 group A Nuclear hormone receptor subfamily 4 group A member 3
- 78 - - -
Unclassified protein
- 900 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Waldenstrom Macroglobulinemia 4 D008258 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 4 D015451 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 3 D016403 ClinicalTrials
Lymphoma, Non-Hodgkin 3 D008228 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Leukemia 2 D007938 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Hodgkin Disease 2 D006689 ClinicalTrials
Carcinoid Tumor 2 D002276 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Leukemia, Hairy Cell 2 D007943 ClinicalTrials
Amyloidosis 2 D000686 ClinicalTrials
Food Hypersensitivity 2 D005512 ClinicalTrials
Lymphoma, B-Cell, Marginal Zone 2 D018442 ClinicalTrials
Anemia, Hemolytic, Autoimmune 2 D000744 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Leukemia, Mast-Cell 2 D007946 ClinicalTrials
Leukemia, Prolymphocytic, T-Cell 2 D015461 ClinicalTrials
Leukemia, Prolymphocytic 2 D015463 ClinicalTrials
Esophageal Neoplasms 2 D004938 ClinicalTrials
Hodgkin Disease 2 D006689 ClinicalTrials
Burkitt Lymphoma 2 D002051 ClinicalTrials
Myelodysplastic Syndromes 1 D009190 ClinicalTrials
Liver Diseases 1 D008107 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Leukemia, Lymphoid 1 D007945 ClinicalTrials
Carcinoma, Renal Cell 1 D002292 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Colorectal Neoplasms 1 D015179 ClinicalTrials
Colonic Neoplasms 1 D003110 ClinicalTrials
Breast Neoplasms 1 D001943 ClinicalTrials
Hematologic Neoplasms 1 D019337 ClinicalTrials
Glioblastoma 1 D005909 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 1 D054198 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 1 D064129 ClinicalTrials
Lung Neoplasms 1 D008175 ClinicalTrials

Related Entries

Scaffolds

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Injury, poisoning and procedural complications
10.43
General disorders and administration site conditions
10.42
Vascular disorders
9.13
Gastrointestinal disorders
8.09
Skin and subcutaneous tissue disorders
7.41
Respiratory, thoracic and mediastinal disorders
6.98
Nervous system disorders
6.49
Investigations
6.4
Musculoskeletal and connective tissue disorders
6.35
Cardiac disorders
5.92
Infections and infestations
5.68
Blood and lymphatic system disorders
3.07
Metabolism and nutrition disorders
2.31
Psychiatric disorders
2.3
Renal and urinary disorders
2.12

Cross References

Resources Reference
CAS NUMBER 936563-96-1
ChEBI 76612
ChEMBL CHEMBL1873475
DrugBank DB09053
DrugCentral 4810
EPA CompTox DTXSID60893450
FDA SRS 1X70OSD4VX
Guide to Pharmacology 6912
KEGG D10223
PDB 1E8
PharmGKB PA166121346
PubChem 24821094
SureChEMBL SCHEMBL201859
ZINC ZINC000035328014
CONTENTS