General
Preferred name
IBRUTINIB
Synonyms
CRA-032765, PCI-32765-00, PCI-32765 ()
PCI-32765 ()
Ibrutinib D5 ()
PCI-32765 D5 ()
PCI 32765 ()
IMBRUVICA ()
CRA-032765 ()
PC-32765 ()
PCI-32765-00 ()
P&D ID
PD003357
CAS
936563-96-1
Tags
PROTAC
probe
covalent binder
drug
available
Approved by
PMDA
EMA
FDA
First approval
2013
Drug Status
approved
Drug indication
Follicular lymphoma
Mantle cell lymphoma
Pancreatic cancer
B-cell non-hodgkin lymphoma
Non-hodgkin lymphoma
Solid tumour/cancer
Diffuse large B-cell lymphoma
Max Phase
Phase 4
Probe info
Probe type
experimental probe
Probe sources
Chemical Probes.org
Probe targets
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION Ibrutinib is approved with breakthrough therapy designation through the FDA's accelerated approval program. This drug has been granted orphan designation by the European Medicines Agency (Nov, 2013) for the treatment of large B-cell lymphoma.
PHARMACODYNAMICS In vitro studies have shown an induction of CLL cell apoptosis even in presence of prosurvival factors. It has also been reported an inhibition of CLL cell survival and proliferation as well as an impaired in cell migration and a reduction in the secretion of chemokines such as CCL3 and CCL4. The latter effect has been shown to produce regression in xenograft mouse models.[A32306]; ; Clinical studies for relapsed/refractory CLL in phase I and II showed an approximate 71% of overall response rate.[A32308, A32309]. In the case of relapsed/refractory mantle cell lymphoma, approximately 70% of the tested patients presented a partial or complete response.[A32308, A32310]. In clinical trials for relapsed/refractory diffuse large B-cell lymphoma, a partial response was found in between 15-20% of the patients studied; while for patients with relapsed/refractory Waldenstrom's macroglobulinemia, a partial response was observed in over 75% of the patients tested. Finally, for patients with relapsed/refractory follicular lymphoma, a partial to complete response was obtained in approximately 54% of the patients.[A32308]
DESCRIPTION Ibrutinib is a clinically used inhibitor of Bruton's tyrosine kinase. It was originally approved with breakthrough therapy designation through the FDA's accelerated approval program. (GtoPdb)
INDICATION Ibrutinib acquired an accelerated approval for the treatment of mantle cell lymphoma who have received at least one prior therapy.[FDA label] Mantle cell lymphoma (MCL) is a B-cell non-Hodgkin lymphoma that develops in the outer edge of a lymph node. MCL is usually diagnosed at late stages and it is easily spread into bone marrow, spleen, liver and gastrointestinal tract.[L1929]; ; Ibrutinib is indicated for the treatment of chronic lymphocytic leukemia (CLL) who have at least one prior therapy.[FDA label] CLL is a type of cancer caused by an overproduction of lymphocytes by the bone marrow. Some of the symptoms include swollen lymph nodes and tiredness.[L1931]; ; Ibrutinib is indicated for the treatment of chronic lymphocytic leukemia (CLL) with 17p deletion.[FDA label] CLL with 17p is a type of leukemia in which a deletion in 17p disrupts the tumor suppressor p53 by deleting one allele of the TP53 gene. The remaining allele is mainly inactivated and thus, this type of leukemia is unresponsive to p53-dependent treatments.[A32305]; ; Ibrutinib is indicated for the treatment of patients with Waldenstrom's Macroglobulinemia (WM).[FDA label] WM, also called lymphoplasmacytic lymphoma, is a type of non-Hodgkin lymphoma in which the cancer cells make large amounts of macroglobulin. The macroglobulin is a monoclonal protein that corresponds to the type of IgM antibodies and the unrestricted formation of this protein causes typical symptoms such as excessive bleeding and effects in vision and nervous system.[L1934]
MOA Covalent Inhibitor (Chemical Probes.org)
DESCRIPTION Ibrutinib was approved by the FDA for the treatment of mantle cell lymphoma, and later in February 2014 for the treatment of chronic lymphocytic leukemia (PKIDB)
DESCRIPTION inhibitor of Bruton's tyrosine kinase (Informer Set)
DESCRIPTION Potent Raf-1 inhibitor; also inhibits VEGFR-2, VEGFR-3, PDGFR-beta, Flt-3 and cKIT (Tocris Bioactive Compound Library)
Cell lines
52
Organisms
0
Compound Sets
33
AdooQ Bioactive Compound Library
A11020
Axon Medchem Screening Library
1858
Cayman Chemical Bioactives
16274
ChEMBL Approved Drugs
CHEMBL1873475
ChEMBL Drugs
CHEMBL1873475
Chemical Probes.org
ibrutinib
Clinical kinase drugs
Concise Guide to Pharmacology 2017/18
6912
Concise Guide to Pharmacology 2019/20
6912
Concise Guide to Pharmacology 2021/22
6912
Concise Guide to Pharmacology 2023/24
6912
CovalentInDB
CI000729
CovBinderInPDB
CBR000201
CBR000451
CBR005475
CBR005476
CBR005477
CBR005478
Drug Repurposing Hub
DrugBank
DB09053
DrugBank Approved Drugs
DB09053
DrugCentral
4810
DrugCentral Approved Drugs
4810
DrugMAP
DMHZCPO
DrugMAP Approved Drugs
DMHZCPO
Enamine BioReference Compounds
Guide to Pharmacology
6912
Informer Set
660994
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL1873475
LSP-OptimalKinase library (Laboratory of Systems Pharmacology)
CHEMBL1873475
MedChem Express Bioactive Compound Library
HY-10997
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
1X70OSD4VX
Other bioactive compounds
PKIDB
ReFrame library
TargetMol Bioactive Compound Library
T1835
Tocris Bioactive Compound Library
6813
External IDs
36
Properties
(calculated by RDKit )
Molecular Weight
440.2
Hydrogen Bond Acceptors
7
Hydrogen Bond Donors
1
Rotatable Bonds
5
Ring Count
5
Aromatic Ring Count
4
cLogP
4.22
TPSA
99.16
Fraction CSP3
0.2
Chiral centers
1.0
Largest ring
6.0
QED
0.47
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
BTK
BLK
BMX
FGR
CSK
BLK, BMX, BTK
BTK inhibitor
Ligands for Target Protein for PROTAC
Compound status
clinical
Pathway
Angiogenesis
Tyrosine Kinase/Adaptors
Protein Tyrosine Kinase/RTK
Primary Target
Bruton's Tyrosine Kinase
MOA
Src
Tyrosine Kinases
Inhibitor
Bruton's Tyrosine Kinase (BTK) Inhibitor
Indication
chronic lymphocytic leukemia (CLL), mantle cell lymphoma (MCL), Waldenstrom's macroglobulinemia (WM)
Biosynthetic Origin
Nucleoside
Therapeutic Indication
Anticancer
Target class
Kinase
Target subclass
TK
Source data