Ibrutinib

Highest phase reached

Approved

www.ebi.ac.uk

Drug type

Small molecule

www.ebi.ac.uk

First approval year

2013

www.ebi.ac.uk

First approval year: 2013
www.ebi.ac.uk

Listing at source: Listed

Highest phase reached: Approved
www.ebi.ac.uk

Drug type: Small molecule
www.ebi.ac.uk

Drug name: Ibrutinib
www.ebi.ac.uk

Molecular weight: 440.51
www.ebi.ac.uk

Structure (SMILES): C=CC(=O)N1CCC[C@@H](n2nc(-c3ccc(Oc4ccccc4)cc3)c3c(N)ncnc32)C1
www.ebi.ac.uk

imbruvica
Imbruvica

carfilzomib ibrutinib
cra 032765
CRA-032765
ibrutinib
Ibrutinib
IBRUTINIB
Ibrutinib (Arm 4)
Ibrutinib (as Subsequent Therapy)
Ibrutinib (Induction)
Ibrutinib (Maintenance)
Ibrutinib (Treatment B)
Ibrutinib (Treatment C)
Ibrutinib (Treatment D)
Ibrutinib (Treatment E)
Ibrutinib (Treatment F)
ibrutinib [INN]
IBRUTINIB [JAN]
IBRUTINIB [MI]
IBRUTINIB [ORANGE BOOK]
IBRUTINIB [USAN]
IBRUTINIB [VANDF]
Ibrutinib [WHO-DD]
Ibrutinib 420 mg
Ibrutinib 560 mg
Ibrutinib 560mg PO daily (Imbruvica)

And 25 more, listed on the interactive page.

ATC classification codes

L01EL01

Sources for recorded values

www.ebi.ac.uk

CAS registry numbers

936563-96-1

ChEMBL ID: CHEMBL1873475
www.ebi.ac.uk

InChIKey: XYFPWWZEPKGCCK-GOSISDBHSA-N
www.ebi.ac.uk

PubChem compound IDs

24821094

RxNorm IDs (RxCUI)

1442981

FDA ingredient codes (UNII)

1X70OSD4VX

Applicant: PHARMACYCLICS LLC
Approval date: 13 Nov 2013
Application number: NDA205552

Status: Authorised
Status date: 21 Oct 2014
Authorisation date: 21 Oct 2014
Approved indications: Imbruvica in combination with rituximab, cyclophosphamide, doxorubicin, vincristine, and prednisolone (IMBRUVICA + R-CHOP) alternating with R-DHAP (or R-DHAOx) without Imbruvica, followed by Imbruvica monotherapy, is indicated for the treatment of adult patients with previously untreated mantle cell lymphoma (MCL) who would be eligible for autologous stem cell transplantation (ASCT).Imbruvica as a single agent is indicated for the treatment of adult patients with relapsed or refractory MCL.Imbruvica as a single agent or in combination with rituximab or obinutuzumab or venetoclax is indicated for the treatment of adult patients with previously untreated chronic lymphocytic leukaemia (CLL) (see section 5.1).Imbruvica as a single agent or in combination with bendamustine and rituximab (BR) is indicated for the treatment of adult patients with CLL who have received at least one prior therapy.Imbruvica as a single agent is indicated for the treatment of adult patients with Waldenström’s macroglobulinaemia (WM) who have received at least one prior therapy, or in first line treatment for patients unsuitable for chemo immunotherapy. IMBRUVICA in combination with rituximab is indicated for the treatment of adult patients with WM.
Product number: EMEA/H/C/003791
Authorisation holder: Janssen-Cilag International NV
Priority medicines scheme: No
Generic: No
Biosimilar: No
Generic medicines: 0
Biosimilar medicines: 0
Advanced therapy: No
Conditional approval: No
Additional monitoring: No
Accelerated assessment: No
Exceptional circumstances: No

Therapeutic areas

Leukemia, Lymphocytic, Chronic, B-Cell
Lymphoma, Mantle-Cell

European medicines record

www.ema.europa.eu

Patents: 187
Designations: 7
Earliest recorded loss of exclusivity: 14 Jun 2039
First in class: Yes
Fast track: Yes
Breakthrough designation: Yes
Orphan designation: No
Priority review: Yes
Orphan exclusivity: No
Accelerated approval: Yes
Availability: Prescription only

Pharmacology name: ibrutinib
Type: Synthetic organic
Drug name stem: -tinib
Approval recorded by Guide to Pharmacology: Yes

Administration routes

Oral

Action
Inhibition
Action type
Inhibitor
Target
epidermal growth factor receptor
Gene symbol
EGFR
Protein identifier
P00533
Median affinity
8.28
Affinity units
pIC50
Action
Inhibition
Action type
Inhibitor
Target
erb-b2 receptor tyrosine kinase 2
Gene symbol
ERBB2
Protein identifier
P04626
Median affinity
8.19
Affinity units
pIC50
Action
Inhibition
Action type
Inhibitor
Target
LCK proto-oncogene, Src family tyrosine kinase
Gene symbol
LCK
Protein identifier
P06239
Median affinity
8.2
Affinity units
pIC50
Action
Inhibition
Action type
Inhibitor
Target
FYN proto-oncogene, Src family tyrosine kinase
Gene symbol
FYN
Protein identifier
P06241
Median affinity
7.54
Affinity units
pIC50
Action
Inhibition
Action type
Inhibitor
Target
YES proto-oncogene 1, Src family tyrosine kinase
Gene symbol
YES1
Protein identifier
P07947
Median affinity
8.39
Affinity units
pIC50
Action
Inhibition
Action type
Inhibitor
Target
LYN proto-oncogene, Src family tyrosine kinase
Gene symbol
LYN
Protein identifier
P07948
Median affinity
7.7
Affinity units
pIC50
Action
Inhibition
Action type
Inhibitor
Target
HCK proto-oncogene, Src family tyrosine kinase
Gene symbol
HCK
Protein identifier
P08631
Median affinity
7.54
Affinity units
pIC50
Action
Inhibition
Action type
Inhibitor
Target
SRC proto-oncogene, non-receptor tyrosine kinase
Gene symbol
SRC
Protein identifier
P12931
Median affinity
7.72
Affinity units
pIC50
Action
Inhibition
Action type
Inhibitor
Target
tec protein tyrosine kinase
Gene symbol
TEC
Protein identifier
P42680
Median affinity
8.15
Affinity units
pIC50
Action
Inhibition
Action type
Inhibitor
Target
TXK tyrosine kinase
Gene symbol
TXK
Protein identifier
P42681
Median affinity
8.7
Affinity units
pIC50
Action
Inhibition
Action type
Inhibitor
Target
BLK proto-oncogene, Src family tyrosine kinase
Gene symbol
BLK
Protein identifier
P51451
Median affinity
9.3
Affinity units
pIC50
Action
Inhibition
Action type
Inhibitor
Target
BMX non-receptor tyrosine kinase
Gene symbol
BMX
Protein identifier
P51813
Median affinity
9.1
Affinity units
pIC50
Action
Inhibition
Action type
Inhibitor
Target
Janus kinase 3
Gene symbol
JAK3
Protein identifier
P52333
Median affinity
7.49
Affinity units
pIC50
Action
Inhibition
Action type
Inhibitor
Target
Bruton tyrosine kinase
Gene symbol
BTK
Protein identifier
Q06187
Median affinity
9.3
Affinity units
pIC50
Primary target
Yes
Action
Inhibition
Action type
Inhibitor
Target
IL2 inducible T cell kinase
Gene symbol
ITK
Protein identifier
Q08881
Median affinity
8.31
Affinity units
pIC50
Action
Inhibition
Action type
Inhibitor
Target
erb-b2 receptor tyrosine kinase 4
Gene symbol
ERBB4
Protein identifier
Q15303
Median affinity
8.47
Affinity units
pIC50
Mechanism
Tyrosine-protein kinase BTK inhibitor
Action type
Inhibitor
Target
Tyrosine-protein kinase BTK
Protein identifier
Q06187

Open Targets mechanisms

Mechanism
Tyrosine-protein kinase BTK inhibitor
Action type
Inhibitor
Target
Tyrosine-protein kinase BTK

Action type
Inhibitor
Gene symbol
ERBB2
Protein identifier
P04626
Organism
Homo sapiens
Target development level
Clinical
Action type
Inhibitor
Gene symbol
LCK
Protein identifier
P06239
Organism
Homo sapiens
Target development level
Clinical
Action type
Inhibitor
Gene symbol
FYN
Protein identifier
P06241
Organism
Homo sapiens
Target development level
Clinical
Action type
Inhibitor
Gene symbol
YES1
Protein identifier
P07947
Organism
Homo sapiens
Target development level
Clinical
Action type
Inhibitor
Gene symbol
HCK
Protein identifier
P08631
Organism
Homo sapiens
Target development level
Clinical
Action type
Inhibitor
Gene symbol
FGR
Protein identifier
P09769
Organism
Homo sapiens
Target development level
Chemical evidence
Action type
Inhibitor
Gene symbol
SRC
Protein identifier
P12931
Organism
Homo sapiens
Target development level
Clinical
Action type
Inhibitor
Gene symbol
TEC
Protein identifier
P42680
Organism
Homo sapiens
Target development level
Chemical evidence
Action type
Inhibitor
Gene symbol
TXK
Protein identifier
P42681
Organism
Homo sapiens
Target development level
Chemical evidence
Action type
Inhibitor
Gene symbol
BLK
Protein identifier
P51451
Organism
Homo sapiens
Target development level
Chemical evidence
Action type
Inhibitor
Gene symbol
JAK3
Protein identifier
P52333
Organism
Homo sapiens
Target development level
Clinical
Action type
Inhibitor
Gene symbol
BTK
Protein identifier
Q06187
Organism
Homo sapiens
Target development level
Clinical
Action type
Inhibitor
Gene symbol
ITK
Protein identifier
Q08881
Organism
Homo sapiens
Target development level
Clinical
Action type
Inhibitor
Gene symbol
ERBB4
Protein identifier
Q15303
Organism
Homo sapiens
Target development level
Clinical

Condition
Leukemia, Lymphocytic, Chronic, B-Cell
Highest recorded phase
4
Condition identifier
EFO:0000095
Subject identifier
D015451
Condition
Lymphoma, Follicular
Highest recorded phase
3
Condition identifier
EFO:0000096
Subject identifier
D008224
Condition
Carcinoma, Squamous Cell
Highest recorded phase
2
Condition identifier
EFO:0000181
Subject identifier
D002294
Condition
Hodgkin Disease
Highest recorded phase
2
Condition identifier
EFO:0000183
Subject identifier
D006689
Condition
Myelodysplastic Syndromes
Highest recorded phase
1
Condition identifier
EFO:0000198
Subject identifier
D009190
Condition
Precursor Cell Lymphoblastic Leukemia-Lymphoma
Highest recorded phase
1
Condition identifier
EFO:0000220
Subject identifier
D054198
Condition
Leukemia, Myeloid, Acute
Highest recorded phase
2
Condition identifier
EFO:0000222
Subject identifier
D015470
Condition
Burkitt Lymphoma
Highest recorded phase
2
Condition identifier
EFO:0000309
Subject identifier
D002051
Condition
Melanoma
Highest recorded phase
2
Condition identifier
EFO:0000389
Subject identifier
D008545
Condition
Lymphoma, Large B-Cell, Diffuse
Highest recorded phase
3
Condition identifier
EFO:0000403
Subject identifier
D016403
Condition
Glioblastoma
Highest recorded phase
1
Condition identifier
EFO:0000519
Subject identifier
D005909
Condition
Leukemia
Highest recorded phase
2
Condition identifier
EFO:0000565
Subject identifier
D007938
Condition
Lymphoma
Highest recorded phase
3
Condition identifier
EFO:0000574
Subject identifier
D008223
Condition
Neoplasms
Highest recorded phase
4
Condition identifier
EFO:0000616
Subject identifier
D009369
Condition
Carcinoma, Renal Cell
Highest recorded phase
1
Condition identifier
EFO:0000681
Subject identifier
D002292
Condition
Multiple Myeloma
Highest recorded phase
2
Condition identifier
EFO:0001378
Subject identifier
D009101
Condition
Liver Diseases
Highest recorded phase
1
Condition identifier
EFO:0001421
Subject identifier
D008107
Condition
Hematologic Neoplasms
Highest recorded phase
2
Condition identifier
EFO:0001642
Subject identifier
D019337
Condition
Waldenstrom Macroglobulinemia
Highest recorded phase
4
Condition identifier
EFO:0002616
Subject identifier
D008258
Condition
Melanoma
Highest recorded phase
2
Condition identifier
EFO:0002617
Subject identifier
D008545
Condition
Carcinoma, Non-Small-Cell Lung
Highest recorded phase
2
Condition identifier
EFO:0003060
Subject identifier
D002289
Condition
Carcinoid Tumor
Highest recorded phase
2
Condition identifier
EFO:0004243
Subject identifier
D002276
Condition
Leukemia, Lymphoid
Highest recorded phase
2
Condition identifier
EFO:0004289
Subject identifier
D007945
Condition
Lymphoma, Non-Hodgkin
Highest recorded phase
3
Condition identifier
EFO:0005952
Subject identifier
D008228
Condition
Head and Neck Neoplasms
Highest recorded phase
2
Condition identifier
EFO:0006859
Subject identifier
D006258

And 24 more, listed on the interactive page.

Condition identifier
EFO_0000095
Condition identifier
EFO_0000096
Highest recorded phase
2
Condition identifier
EFO_0000183
Highest recorded phase
2
Condition identifier
EFO_0000198
Highest recorded phase
1
Condition identifier
EFO_0000222
Condition identifier
EFO_0000389
Highest recorded phase
2
Condition identifier
EFO_0000403
Highest recorded phase
3
Condition identifier
EFO_0000519
Highest recorded phase
1
Condition identifier
EFO_0000565
Highest recorded phase
2
Condition identifier
EFO_0000574
Highest recorded phase
3
Condition identifier
EFO_0000616
Condition identifier
EFO_0000681
Condition identifier
EFO_0001378
Highest recorded phase
2
Condition identifier
EFO_0001421
Highest recorded phase
1
Condition identifier
EFO_0002616
Condition identifier
EFO_0002616
Highest recorded phase
4
Condition identifier
EFO_0002617
Highest recorded phase
2
Condition identifier
EFO_0003060
Highest recorded phase
2
Condition identifier
EFO_0003860
Highest recorded phase
3
Condition identifier
EFO_0004289
Highest recorded phase
2
Condition identifier
EFO_0005952
Highest recorded phase
3
Condition identifier
EFO_0007359
Highest recorded phase
2
Condition identifier
EFO_0009441
Highest recorded phase
3
Condition identifier
EFO_1000157
Highest recorded phase
2
Condition identifier
EFO_1000359
Highest recorded phase
3

And 71 more, listed on the interactive page.

Event
atrial fibrillation
Reports
1,004
Reporting signal score
1,643.98
Event
cerebral aspergillosis
Reports
47
Reporting signal score
173.645
Event
chronic lymphocytic leukaemia
Reports
149
Reporting signal score
404.348
Event
contusion
Reports
414
Reporting signal score
459.827
Event
drug hypersensitivity
Reports
16
Reporting signal score
165.26
Event
epistaxis
Reports
245
Reporting signal score
165.838
Event
haematoma
Reports
195
Reporting signal score
215.502
Event
haemorrhage
Reports
500
Reporting signal score
554.015
Event
injection site pain
Reports
1
Reporting signal score
169.734
Event
lymphadenopathy
Reports
222
Reporting signal score
248.083
Event
lymphocyte count increased
Reports
82
Reporting signal score
190.797
Event
lymphocytosis
Reports
119
Reporting signal score
336.138
Event
pericardial effusion
Reports
150
Reporting signal score
165.267
Event
petechiae
Reports
151
Reporting signal score
265.706
Event
platelet count decreased
Reports
386
Reporting signal score
238.548
Event
pleural effusion
Reports
304
Reporting signal score
265.402
Event
pneumonia
Reports
599
Reporting signal score
219.549
Event
richter's syndrome
Reports
57
Reporting signal score
202.85
Event
subdural haematoma
Reports
130
Reporting signal score
183.969
Event
tumour lysis syndrome
Reports
109
Reporting signal score
187.691
Event
white blood cell count increased
Reports
242
Reporting signal score
243.355

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And 237 more, listed on the interactive page.

Dose: 420 mg
Route: Oral
How often: Once daily

Hydrogen bond acceptors: 7
Hydrogen bond donors: 1
Polar surface area: 99.16
Calculated partition coefficient (ALogP): 4.22
Calculated partition coefficient (XLogP): 3.6
Prodrug: No
Chirality: Single enantiomer
Inorganic: No
Rule-of-five violations: 0
Rotatable bonds: 5
Heavy atoms: 33
Molecular formula: C25H24N6O2
Monoisotopic mass: 440.19607403
Natural product: Yes

57962-007
57962-014
57962-070
57962-140
57962-280
57962-420

Recorded assays: 2,122
Active assays: 768

Confirmatory
Other
Screening

Tyrosine Kinase Inhibitors
id.nlm.nih.gov

These details could not be displayed.

Related records

Trials (682)

A 2×2 Factorial Randomized Controlled Trial for ERCP
A 5-treatment, Study in Healthy Volunteers to Assess The Safety, Tolerability, and Pharmacokinetics of Four Controlled Release (CR) Pregabalin Tablet Formulations and the Immediate Release (IR) Formulation Administered Fasted
A Clinical Study of iNSC Intervent Cerebral Hemorrhagic Stroke
A Clinical Study on the Treatment of LACC With Cadonilimab Combined With Chemotherapy Followed by CCRT
A Clinical Trial of Buparlisib and Ibrutinib in Lymphoma
A Comparative Bioavailability and Pharmacokinetic Study of TNX-102 2.4 mg and Cyclobenzaprine 5 mg Tablets in Healthy Adults.
A Comparison Between Propofol and Etomidate in Hysteroscopy on Effect of Postoperative Sedation and Cognitive Function in Elderly Patients
A Comparison of Inhalation vs. Intravenous Induction
A Crossover Study to Evaluate Relative Bioavailability of Simeprevir Age-appropriate Oral Formulation Candidates Compared With 150-milligram (mg) Oral Capsule in Healthy Adult Participants
A Crossover Study to Evaluate the Bioavailability of Ibrutinib Suspension and Sprinkle Formulations Compared to Capsules in Healthy Adults
A Drug Interaction Study to Assess the Effect of Omeprazole on the Pharmacokinetics of Ibrutinib in Healthy Adults
A Drug-Drug Interaction Study of CTL0901 and CTL0902 Compared to Coadministration in Healthy Adult Volunteers
A Long-term Extension Study of PCI-32765 (Ibrutinib)
A Multi-Center Study of Ibrutinib in Combination With MEDI4736 in Subjects With Relapsed or Refractory Lymphomas
A Multi-Center Study of Ibrutinib in Combination With MEDI4736 in Subjects With Relapsed or Refractory Solid Tumors
A Multi-Center Study of Ibrutinib in Combination With Obinutuzumab Versus Chlorambucil in Combination With Obinutuzumab in Patients With Treatment naïve Chronic Lymphocytic Leukemia (CLL) or Small Lymphocytic Lymphoma (SLL)
A Multicenter Phase 2 Study of Ibrutinib in Patients With Relapsed or Refractory Chronic Lymphocytic Leukemia (CLL) or Small Lymphocytic Lymphoma (SLL) With 17p Deletion
A Multicenter Randomized Controlled Clinical Study on the Treatment of T3N1M0 High Risk Nasopharyngeal Carcinoma With or Without Induction Chemotherapy Before Concurrent Radiotherapy and Chemotherapy
A Phase 1 Drug Drug Interaction Clinical Trial of C1-R215 and C2-R215 in Healthy Male Volunteers
A Phase 1 Study of Novel GS-9973 Tablet Formulations to Evaluate the Effect of Acid Reducing Agents, Relative Bioavailability, and Food Effect on GS-9973 Pharmacokinetics

Approved for (5)

In development for (48)

Acute lymphoblastic leukemia Phase 1
Acute myeloid leukemia Phase 2
Amyloidosis Phase 2
Anaphylaxis Phase 2
Autoimmune hemolytic anemia Phase 2
B-cell non-Hodgkin lymphoma Phase 3
Breast cancer Phase 1
Burkitt lymphoma Phase 2
Carcinoid tumor Phase 2
Chronic graft versus host disease Phase 3
Classic Hodgkin lymphoma Phase 2
Colorectal cancer Phase 1
COVID-19 Phase 2
Cutaneous melanoma Phase 2
Diffuse large B-cell lymphoma Phase 3
Esophageal cancer Phase 2
Follicular lymphoma Phase 3
Food allergy Phase 2
Glioblastoma Phase 1
Graft versus host disease Phase 3

Targets (1)

BTK Tyrosine-protein kinase BTK inhibitor

Ibrutinib

Development status

Names and chemistry

Brand names (2)

Other names (50)

Identifiers

Regulatory information

United States

European Union

Therapeutic areas

Other regulatory facts

Pharmacology

Drug classification

Administration routes

Mechanisms of action (17)

Open Targets mechanisms

DrugCentral mechanisms (14)

Investigated indications (49)

Open Targets indications (96)

Reported adverse events (21)

Trial references (262)

Dosing

Chemical properties

National Drug Codes

Evidence counts

Active assay types (3)

Pharmacologic actions

Biological measurements

Related records

Trials (682)

Approved for (5)

In development for (48)

Targets (1)