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Identification
NameIbrutinib
Accession NumberDB09053
TypeSmall Molecule
GroupsApproved
DescriptionIbrutinib is a small molecule anti-cancer drug that targets B-cell malignancies. In November 2013 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. Ibrutinib is also indicated for the treatment of patients with Waldenström's Macroglobulinemia (WM). Ibrutinib is marketed under the brand Imbruvica® by Janssen Biotech, Inc., but was first designed and synthesized at Celera Genomics in 2007.
Structure
Thumb
Synonyms
1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one
External Identifiers
  • PCI-32765
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ImbruvicaCapsule140 mgOralJanssen Inc2014-11-19Not applicableCanada
ImbruvicaCapsule140 mgOralJanssen Cilag International Nv2014-10-21Not applicableEu
ImbruvicaCapsule140 mgOralJanssen Cilag International Nv2014-10-21Not applicableEu
ImbruvicaCapsule140 mg/1OralPharmacyclics Llc2013-11-07Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII1X70OSD4VX
CAS number936563-96-1
WeightAverage: 440.507
Monoisotopic: 440.196074037
Chemical FormulaC25H24N6O2
InChI KeyXYFPWWZEPKGCCK-GOSISDBHSA-N
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
IUPAC Name
1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one
SMILES
NC1=NC=NC2=C1C(=NN2[C@@H]1CCCN(C1)C(=O)C=C)C1=CC=C(OC2=CC=CC=C2)C=C1
Pharmacology
IndicationIbrutinib was approved by the FDA for the treatment of mantle cell lymphoma, and later in February 2014 for the treatment of chronic lymphocytic leukemia. Ibrutinib is also indicated for the treatment of patients with Waldenström's Macroglobulinemia (WM).
Structured Indications
PharmacodynamicsIn patients with recurrent B-cell lymphoma > 90% occupancy of the BTK active site in peripheral blood mononuclear cells was observed up to 24 hours after ibrutinib doses of ≥ 2.5 mg/kg/day (≥ 175 mg/day for average weight of 70 kg).
Mechanism of actionIbrutinib is an inhibitor of Bruton’s tyrosine kinase (BTK). It forms a covalent bond with a cysteine residue in the active site of BTK, leading to its inhibition. BTK plays a role in signalling through the B-cell surface receptors which results in the activation of various pathways necessary for B-cell trafficking, chemotaxis, and adhesion. Ibrutinib has been shown to inhibit malignant B cell proliferation and survival in vivo as well as substrate adhesion and cell migration.
TargetKindPharmacological actionActionsOrganismUniProt ID
Tyrosine-protein kinase BTKProteinyes
inhibitor
HumanQ06187 details
Related Articles
AbsorptionMedian Tmax of 1-2 hours. Steady-state AUC at 560 mg: 953 ± 705 ng⋅h/mL Steady-state AUC at 420 mg: 680 ± 517 ng⋅h/mL
Volume of distribution

~10000 L at steady-state.

Protein binding97.3%.
Metabolism

It is metabolized to several metabolites primarily by cytochrome P450, CYP3A, and to a minor extent by CYP2D6. The active metabolite, PCI-45227, is a dihydrodiol metabolite with inhibitory activity towards BTK approximately 15 times lower than that of ibrutinib. The range of the mean metabolite to parent ratio for PCI-45227 at steady-state is 1 to 2.8.

Route of eliminationFeces (80%), urine (10%).
Half life4-6 hours.
Clearance

~1000 L/h, and is not affected by age or gender.

ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbciximabThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Abciximab.Approved
AbirateroneThe serum concentration of Ibrutinib can be increased when it is combined with Abiraterone.Approved
AcenocoumarolThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Acenocoumarol.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Ibrutinib.Approved
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Acetylsalicylic acid.Approved, Vet Approved
AlprostadilThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Alprostadil.Approved, Investigational
ALT-110The risk or severity of adverse effects can be increased when Ibrutinib is combined with ALT-110.Investigational
AmiodaroneThe serum concentration of Ibrutinib can be increased when it is combined with Amiodarone.Approved, Investigational
AnagrelideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Anagrelide.Approved
AncrodThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ancrod.Investigational
Antithrombin III humanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Antithrombin III human.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Ibrutinib.Investigational
ApixabanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Apixaban.Approved
AprepitantThe serum concentration of Ibrutinib can be increased when it is combined with Aprepitant.Approved, Investigational
ArdeparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ardeparin.Approved, Withdrawn
ArgatrobanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Argatroban.Approved, Investigational
ArtemetherThe metabolism of Ibrutinib can be decreased when combined with Artemether.Approved
AtazanavirThe serum concentration of Ibrutinib can be increased when it is combined with Atazanavir.Approved, Investigational
AtomoxetineThe serum concentration of Ibrutinib can be increased when it is combined with Atomoxetine.Approved
AzelastineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Azelastine.Approved
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Ibrutinib.Investigational
BecaplerminThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Becaplermin.Approved, Investigational
BeraprostThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Beraprost.Investigational
BetaxololThe metabolism of Ibrutinib can be decreased when combined with Betaxolol.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Ibrutinib.Approved, Investigational
BexaroteneThe serum concentration of Ibrutinib can be decreased when it is combined with Bexarotene.Approved, Investigational
BivalirudinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of Ibrutinib can be increased when it is combined with Boceprevir.Approved
BortezomibThe serum concentration of Ibrutinib can be increased when it is combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Ibrutinib can be decreased when it is combined with Bosentan.Approved, Investigational
BupropionThe metabolism of Ibrutinib can be decreased when combined with Bupropion.Approved
ButylphthalideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Butylphthalide.Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Ibrutinib.Approved
CangrelorThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Cangrelor.Approved
CarbamazepineThe serum concentration of Ibrutinib can be decreased when it is combined with Carbamazepine.Approved, Investigational
CDX-110The risk or severity of adverse effects can be increased when Ibrutinib is combined with CDX-110.Investigational
CelecoxibThe metabolism of Ibrutinib can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Ibrutinib can be increased when it is combined with Ceritinib.Approved
CertoparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Certoparin.Approved
ChloroquineThe metabolism of Ibrutinib can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe metabolism of Ibrutinib can be decreased when combined with Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Ibrutinib can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CilostazolThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Cilostazol.Approved
CimetidineThe metabolism of Ibrutinib can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Ibrutinib can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Ibrutinib can be decreased when combined with Citalopram.Approved
Citric AcidThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Citric Acid.Nutraceutical, Vet Approved
ClarithromycinThe serum concentration of Ibrutinib can be increased when it is combined with Clarithromycin.Approved
ClemastineThe serum concentration of Ibrutinib can be increased when it is combined with Clemastine.Approved
ClobazamThe metabolism of Ibrutinib can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Ibrutinib can be decreased when combined with Clomipramine.Approved, Vet Approved
ClopidogrelThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe serum concentration of Ibrutinib can be increased when it is combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Clozapine.Approved
CobicistatThe serum concentration of Ibrutinib can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Ibrutinib can be decreased when combined with Cocaine.Approved, Illicit
ConivaptanThe serum concentration of Ibrutinib can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe serum concentration of Ibrutinib can be increased when it is combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Ibrutinib.Approved, Investigational
CyclosporineThe serum concentration of Ibrutinib can be increased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dabigatran etexilate.Approved
DabrafenibThe serum concentration of Ibrutinib can be decreased when it is combined with Dabrafenib.Approved
DalteparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dalteparin.Approved
DanaparoidThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Danaparoid.Approved, Withdrawn
DarifenacinThe metabolism of Ibrutinib can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Ibrutinib can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Ibrutinib can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Ibrutinib can be decreased when it is combined with Deferasirox.Approved, Investigational
DefibrotideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Defibrotide.Approved, Investigational
DelavirdineThe serum concentration of Ibrutinib can be increased when it is combined with Delavirdine.Approved
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Ibrutinib.Approved
DesipramineThe metabolism of Ibrutinib can be decreased when combined with Desipramine.Approved
DesirudinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Desirudin.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Ibrutinib.Approved
DexamethasoneThe serum concentration of Ibrutinib can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextranThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dextran.Approved, Vet Approved
Dextran 40The risk or severity of adverse effects can be increased when Ibrutinib is combined with Dextran 40.Approved
Dextran 70The risk or severity of adverse effects can be increased when Ibrutinib is combined with Dextran 70.Approved
Dextran 75The risk or severity of adverse effects can be increased when Ibrutinib is combined with Dextran 75.Approved
DicoumarolThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dicoumarol.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Ibrutinib.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Ibrutinib.Approved
DihydroergotamineThe serum concentration of Ibrutinib can be increased when it is combined with Dihydroergotamine.Approved
DiltiazemThe serum concentration of Ibrutinib can be increased when it is combined with Diltiazem.Approved
DiphenhydramineThe metabolism of Ibrutinib can be decreased when combined with Diphenhydramine.Approved
DipyridamoleThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dipyridamole.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Ibrutinib.Approved, Investigational
DoxycyclineThe serum concentration of Ibrutinib can be increased when it is combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe serum concentration of Ibrutinib can be increased when it is combined with Dronedarone.Approved
DuloxetineThe metabolism of Ibrutinib can be decreased when combined with Duloxetine.Approved
Edetic AcidThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Edetic Acid.Approved, Vet Approved
EdoxabanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Edoxaban.Approved
EfavirenzThe serum concentration of Ibrutinib can be decreased when it is combined with Efavirenz.Approved, Investigational
EliglustatThe metabolism of Ibrutinib can be decreased when combined with Eliglustat.Approved
EnoxaparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Enoxaparin.Approved
EnzalutamideThe serum concentration of Ibrutinib can be decreased when it is combined with Enzalutamide.Approved
EpinastineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Epinastine.Approved, Investigational
eplivanserineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with eplivanserine.Investigational
EpoprostenolThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Epoprostenol.Approved
EptifibatideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Eptifibatide.Approved, Investigational
ErythromycinThe serum concentration of Ibrutinib can be increased when it is combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Ibrutinib can be decreased when it is combined with Eslicarbazepine acetate.Approved
Ethyl biscoumacetateThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ethyl biscoumacetate.Withdrawn
EtravirineThe serum concentration of Ibrutinib can be decreased when it is combined with Etravirine.Approved
FingolimodIbrutinib may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FluconazoleThe serum concentration of Ibrutinib can be increased when it is combined with Fluconazole.Approved
FluindioneThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Fluindione.Investigational
FluoxetineThe metabolism of Ibrutinib can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvoxamineThe serum concentration of Ibrutinib can be increased when it is combined with Fluvoxamine.Approved, Investigational
FondaparinuxThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Fondaparinux.Investigational
Fondaparinux sodiumThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Fondaparinux sodium.Approved, Investigational
FosamprenavirThe serum concentration of Ibrutinib can be increased when it is combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Ibrutinib can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe serum concentration of Ibrutinib can be decreased when it is combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Ibrutinib can be increased when it is combined with Fusidic Acid.Approved
G17DTThe risk or severity of adverse effects can be increased when Ibrutinib is combined with G17DT.Investigational
GabexateThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Gabexate.Investigational
GI-5005The risk or severity of adverse effects can be increased when Ibrutinib is combined with GI-5005.Investigational
HaloperidolThe metabolism of Ibrutinib can be decreased when combined with Haloperidol.Approved
HeparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Heparin.Approved, Investigational
HirulogThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Hirulog.Experimental
IbudilastThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ibudilast.Approved, Investigational
Icosapent ethylThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Icosapent ethyl.Approved, Nutraceutical
IdelalisibThe serum concentration of Ibrutinib can be increased when it is combined with Idelalisib.Approved
idraparinuxThe risk or severity of adverse effects can be increased when Ibrutinib is combined with idraparinux.Investigational
IfenprodilThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ifenprodil.Approved, Withdrawn
IloprostThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Iloprost.Approved, Investigational
ImatinibThe serum concentration of Ibrutinib can be increased when it is combined with Imatinib.Approved
ImipramineThe metabolism of Ibrutinib can be decreased when combined with Imipramine.Approved
IndinavirThe serum concentration of Ibrutinib can be increased when it is combined with Indinavir.Approved
INGN 201The risk or severity of adverse effects can be increased when Ibrutinib is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Ibrutinib is combined with INGN 225.Investigational
IsavuconazoniumThe serum concentration of Ibrutinib can be increased when it is combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Ibrutinib can be decreased when combined with Isoniazid.Approved
IsradipineThe serum concentration of Ibrutinib can be increased when it is combined with Isradipine.Approved
ItraconazoleThe serum concentration of Ibrutinib can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Ibrutinib can be increased when it is combined with Ivacaftor.Approved
KetanserinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ketanserin.Investigational
KetoconazoleThe serum concentration of Ibrutinib can be increased when it is combined with Ketoconazole.Approved, Investigational
LeflunomideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Leflunomide.Approved, Investigational
LepirudinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Lepirudin.Approved
LopinavirThe serum concentration of Ibrutinib can be increased when it is combined with Lopinavir.Approved
LorcaserinThe metabolism of Ibrutinib can be decreased when combined with Lorcaserin.Approved
LovastatinThe serum concentration of Ibrutinib can be increased when it is combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Ibrutinib can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Ibrutinib can be decreased when it is combined with Lumacaftor.Approved
LumefantrineThe metabolism of Ibrutinib can be decreased when combined with Lumefantrine.Approved
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Ibrutinib.Withdrawn
MethadoneThe metabolism of Ibrutinib can be decreased when combined with Methadone.Approved
MethotrimeprazineThe metabolism of Ibrutinib can be decreased when combined with Methotrimeprazine.Approved
MetoprololThe metabolism of Ibrutinib can be decreased when combined with Metoprolol.Approved, Investigational
MifepristoneThe serum concentration of Ibrutinib can be increased when it is combined with Mifepristone.Approved, Investigational
MilrinoneThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Milrinone.Approved
MirabegronThe metabolism of Ibrutinib can be decreased when combined with Mirabegron.Approved
MitotaneThe serum concentration of Ibrutinib can be decreased when it is combined with Mitotane.Approved
ModafinilThe serum concentration of Ibrutinib can be decreased when it is combined with Modafinil.Approved, Investigational
NadroparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Nadroparin.Approved
NafamostatThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Nafamostat.Investigational
NafcillinThe serum concentration of Ibrutinib can be decreased when it is combined with Nafcillin.Approved
NaftopidilThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Naftopidil.Investigational
NatalizumabThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Natalizumab.Approved, Investigational
NCX 4016The risk or severity of adverse effects can be increased when Ibrutinib is combined with NCX 4016.Investigational
NefazodoneThe serum concentration of Ibrutinib can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Ibrutinib can be increased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Ibrutinib can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Ibrutinib can be increased when it is combined with Nevirapine.Approved
NicardipineThe metabolism of Ibrutinib can be decreased when combined with Nicardipine.Approved
NilotinibThe serum concentration of Ibrutinib can be increased when it is combined with Nilotinib.Approved, Investigational
NimesulideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Nimesulide.Approved, Withdrawn
NitroaspirinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Nitroaspirin.Investigational
OlaparibThe serum concentration of Ibrutinib can be increased when it is combined with Olaparib.Approved
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Ibrutinib.Approved
OsimertinibThe serum concentration of Ibrutinib can be increased when it is combined with Osimertinib.Approved
OtamixabanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Otamixaban.Investigational
OuabainOuabain may decrease the cardiotoxic activities of Ibrutinib.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Ibrutinib.Approved, Vet Approved
PalbociclibThe serum concentration of Ibrutinib can be increased when it is combined with Palbociclib.Approved
PanobinostatThe serum concentration of Ibrutinib can be increased when it is combined with Panobinostat.Approved, Investigational
ParoxetineThe metabolism of Ibrutinib can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Ibrutinib can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe serum concentration of Ibrutinib can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Pentosan Polysulfate.Approved
PentoxifyllineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Pentoxifylline.Approved, Investigational
PhenindioneThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Phenindione.Approved
PhenobarbitalThe serum concentration of Ibrutinib can be decreased when it is combined with Phenobarbital.Approved
PhenprocoumonThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Phenprocoumon.Approved
PhenytoinThe serum concentration of Ibrutinib can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Ibrutinib.Approved, Investigational
PosaconazoleThe serum concentration of Ibrutinib can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PrasugrelThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Prasugrel.Approved
PrimidoneThe serum concentration of Ibrutinib can be decreased when it is combined with Primidone.Approved, Vet Approved
PromazineThe metabolism of Ibrutinib can be decreased when combined with Promazine.Approved, Vet Approved
Protein CThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Protein C.Approved
Protein S humanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Protein S human.Approved
ProtocatechualdehydeThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Protocatechualdehyde.Approved
QuinidineThe metabolism of Ibrutinib can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Ibrutinib can be decreased when combined with Quinine.Approved
Rabies vaccineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Rabies vaccine.Approved
Rabies vaccineThe therapeutic efficacy of Rabies vaccine can be decreased when used in combination with Ibrutinib.Approved
RamatrobanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ramatroban.Investigational
RanolazineThe serum concentration of Ibrutinib can be increased when it is combined with Ranolazine.Approved, Investigational
ResveratrolThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Resveratrol.Experimental, Investigational
ReviparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Reviparin.Approved
RidogrelThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ridogrel.Approved
RifabutinThe serum concentration of Ibrutinib can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Ibrutinib can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Ibrutinib can be decreased when it is combined with Rifapentine.Approved
RitonavirThe serum concentration of Ibrutinib can be increased when it is combined with Ritonavir.Approved, Investigational
RivaroxabanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Rivaroxaban.Approved
RoflumilastRoflumilast may increase the immunosuppressive activities of Ibrutinib.Approved
RolapitantThe metabolism of Ibrutinib can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Ibrutinib can be decreased when combined with Ropinirole.Approved, Investigational
SaquinavirThe serum concentration of Ibrutinib can be increased when it is combined with Saquinavir.Approved, Investigational
SCH-530348The risk or severity of adverse effects can be increased when Ibrutinib is combined with SCH-530348.Investigational
SertralineThe metabolism of Ibrutinib can be decreased when combined with Sertraline.Approved
SevofluraneThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Sevoflurane.Approved, Vet Approved
SildenafilThe serum concentration of Ibrutinib can be increased when it is combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Ibrutinib can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Ibrutinib can be increased when it is combined with Simeprevir.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Ibrutinib.Approved
SRP 299The risk or severity of adverse effects can be increased when Ibrutinib is combined with SRP 299.Investigational
SRT501The risk or severity of adverse effects can be increased when Ibrutinib is combined with SRT501.Investigational
St. John's WortThe serum concentration of Ibrutinib can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Ibrutinib can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe serum concentration of Ibrutinib can be increased when it is combined with Sulfisoxazole.Approved, Vet Approved
SulodexideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Sulodexide.Approved, Investigational
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Ibrutinib.Approved, Investigational
TelaprevirThe serum concentration of Ibrutinib can be increased when it is combined with Telaprevir.Approved
TelithromycinThe serum concentration of Ibrutinib can be increased when it is combined with Telithromycin.Approved
TerbinafineThe metabolism of Ibrutinib can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TesmilifeneThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Tesmilifene.Investigational
TG4010The risk or severity of adverse effects can be increased when Ibrutinib is combined with TG4010.Investigational
ThioridazineThe metabolism of Ibrutinib can be decreased when combined with Thioridazine.Approved
TiclopidineThe serum concentration of Ibrutinib can be increased when it is combined with Ticlopidine.Approved
TipranavirThe metabolism of Ibrutinib can be decreased when combined with Tipranavir.Approved, Investigational
TirofibanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Tirofiban.Approved
TocilizumabThe serum concentration of Ibrutinib can be decreased when it is combined with Tocilizumab.Approved
TofacitinibIbrutinib may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TranilastThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Tranilast.Approved, Investigational
TranylcypromineThe metabolism of Ibrutinib can be decreased when combined with Tranylcypromine.Approved
TrapidilThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Trapidil.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Ibrutinib.Approved, Investigational
TriflusalThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Triflusal.Approved
VenlafaxineThe serum concentration of Ibrutinib can be increased when it is combined with Venlafaxine.Approved
VerapamilThe serum concentration of Ibrutinib can be increased when it is combined with Verapamil.Approved
Vitamin EVitamin E may increase the antiplatelet activities of Ibrutinib.Approved, Nutraceutical, Vet Approved
VorapaxarThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Vorapaxar.Approved
VoriconazoleThe serum concentration of Ibrutinib can be increased when it is combined with Voriconazole.Approved, Investigational
WarfarinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Warfarin.Approved
XimelagatranThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ximelagatran.Approved, Investigational, Withdrawn
Ym150The risk or severity of adverse effects can be increased when Ibrutinib is combined with Ym150.Investigational
ZiprasidoneThe serum concentration of Ibrutinib can be increased when it is combined with Ziprasidone.Approved
Food Interactions
  • Administration with food increases ibrutinib exposure approximately 2-fold compared with administration after overnight fasting.
References
Synthesis ReferenceNot Available
General References
  1. Bagcchi S: Ibrutinib in pretreated Waldenstrom's macroglobulinaemia. Lancet Oncol. 2015 May;16(5):e204. doi: 10.1016/S1470-2045(15)70185-3. Epub 2015 Apr 16. [PubMed:25892147 ]
  2. Kim ES, Dhillon S: Ibrutinib: a review of its use in patients with mantle cell lymphoma or chronic lymphocytic leukaemia. Drugs. 2015 May;75(7):769-76. doi: 10.1007/s40265-015-0380-3. [PubMed:25802231 ]
  3. Scheers E, Leclercq L, de Jong J, Bode N, Bockx M, Laenen A, Cuyckens F, Skee D, Murphy J, Sukbuntherng J, Mannens G: Absorption, metabolism, and excretion of oral (1)(4)C radiolabeled ibrutinib: an open-label, phase I, single-dose study in healthy men. Drug Metab Dispos. 2015 Feb;43(2):289-97. doi: 10.1124/dmd.114.060061. Epub 2014 Dec 8. [PubMed:25488930 ]
External Links
ATC CodesL01XE27
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (579 KB)
MSDSDownload (24.9 KB)
ADMET
Predicted ADMET featuresNot Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
CapsuleOral140 mg
CapsuleOral140 mg/1
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7514444 No2006-12-282026-12-28Us
US8008309 No2006-12-282026-12-28Us
US8476284 No2006-12-282026-12-28Us
US8497277 No2006-12-282026-12-28Us
US8697711 No2006-12-282026-12-28Us
US8703780 No2006-12-282026-12-28Us
US8735403 No2006-12-282026-12-28Us
US8754090 No2011-06-032031-06-03Us
US8754091 No2006-12-282026-12-28Us
US8957079 No2006-12-282026-12-28Us
US8999999 No2011-06-032031-06-03Us
US9125889 No2011-06-032031-06-03Us
US9181257 No2006-12-282026-12-28Us
US9296753 No2013-10-302033-10-30Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0203 mg/mLALOGPS
logP2.76ALOGPS
logP3.63ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)19.7ChemAxon
pKa (Strongest Basic)6.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area99.16 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity138.07 m3·mol-1ChemAxon
Polarizability47.84 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
ClassificationNot classified

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Protein tyrosine kinase activity
Specific Function:
Non-receptor tyrosine kinase indispensable for B lymphocyte development, differentiation and signaling. Binding of antigen to the B-cell antigen receptor (BCR) triggers signaling that ultimately leads to B-cell activation. After BCR engagement and activation at the plasma membrane, phosphorylates PLCG2 at several sites, igniting the downstream signaling pathway through calcium mobilization, fol...
Gene Name:
BTK
Uniprot ID:
Q06187
Molecular Weight:
76280.71 Da
References
  1. Kim ES, Dhillon S: Ibrutinib: a review of its use in patients with mantle cell lymphoma or chronic lymphocytic leukaemia. Drugs. 2015 May;75(7):769-76. doi: 10.1007/s40265-015-0380-3. [PubMed:25802231 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Scheers E, Leclercq L, de Jong J, Bode N, Bockx M, Laenen A, Cuyckens F, Skee D, Murphy J, Sukbuntherng J, Mannens G: Absorption, metabolism, and excretion of oral (1)(4)C radiolabeled ibrutinib: an open-label, phase I, single-dose study in healthy men. Drug Metab Dispos. 2015 Feb;43(2):289-97. doi: 10.1124/dmd.114.060061. Epub 2014 Dec 8. [PubMed:25488930 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Scheers E, Leclercq L, de Jong J, Bode N, Bockx M, Laenen A, Cuyckens F, Skee D, Murphy J, Sukbuntherng J, Mannens G: Absorption, metabolism, and excretion of oral (1)(4)C radiolabeled ibrutinib: an open-label, phase I, single-dose study in healthy men. Drug Metab Dispos. 2015 Feb;43(2):289-97. doi: 10.1124/dmd.114.060061. Epub 2014 Dec 8. [PubMed:25488930 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Scheers E, Leclercq L, de Jong J, Bode N, Bockx M, Laenen A, Cuyckens F, Skee D, Murphy J, Sukbuntherng J, Mannens G: Absorption, metabolism, and excretion of oral (1)(4)C radiolabeled ibrutinib: an open-label, phase I, single-dose study in healthy men. Drug Metab Dispos. 2015 Feb;43(2):289-97. doi: 10.1124/dmd.114.060061. Epub 2014 Dec 8. [PubMed:25488930 ]
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Drug created on May 07, 2015 13:33 / Updated on December 03, 2016 03:45