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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 mg/1oralPharmacyclics Llc2013-11-07Not applicableUs
Imbruvicacapsule140 mgoralJanssen Inc2014-11-19Not applicableCanada
ImbruvicaCapsule, hard140 mgOral useJanssen Cilag International Nv2014-10-21Not applicableEu
ImbruvicaCapsule, hard140 mgOral useJanssen Cilag International Nv2014-10-21Not applicableEu
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
Taxonomy
ClassificationNot classified
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).
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.
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
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal AbsorptionNot AvailableNot Available
Blood Brain BarrierNot AvailableNot Available
Caco-2 permeableNot AvailableNot Available
P-glycoprotein substrateNot AvailableNot Available
P-glycoprotein inhibitor INot AvailableNot Available
P-glycoprotein inhibitor IINot AvailableNot Available
Renal organic cation transporterNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 1A2 substrateNot AvailableNot Available
CYP450 2C9 inhibitorNot AvailableNot Available
CYP450 2D6 inhibitorNot AvailableNot Available
CYP450 2C19 inhibitorNot AvailableNot Available
CYP450 3A4 inhibitorNot AvailableNot Available
CYP450 inhibitory promiscuityNot AvailableNot Available
Ames testNot AvailableNot Available
CarcinogenicityNot AvailableNot Available
BiodegradationNot AvailableNot Available
Rat acute toxicityNot AvailableNot applicable
hERG inhibition (predictor I)Not AvailableNot Available
hERG inhibition (predictor II)Not AvailableNot Available
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Capsuleoral140 mg/1
Capsuleoral140 mg
Capsule, hardOral use140 mg
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
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)
Interactions
Drug Interactions
Drug
AbciximabThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Abciximab.
AbirateroneThe metabolism of Ibrutinib can be decreased when combined with Abiraterone.
AcenocoumarolThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Acenocoumarol.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Ibrutinib.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Acetylsalicylic acid.
AlprostadilThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Alprostadil.
AmiodaroneThe serum concentration of Ibrutinib can be increased when it is combined with Amiodarone.
AnagrelideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Anagrelide.
AncrodThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ancrod.
Antithrombin III humanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Antithrombin III human.
ApixabanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Apixaban.
AprepitantThe serum concentration of Ibrutinib can be increased when it is combined with Aprepitant.
ArdeparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ardeparin.
ArgatrobanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Argatroban.
ArtemetherThe metabolism of Ibrutinib can be decreased when combined with Artemether.
AtazanavirThe serum concentration of Ibrutinib can be increased when it is combined with Atazanavir.
AtomoxetineThe serum concentration of Ibrutinib can be increased when it is combined with Atomoxetine.
AzelastineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Azelastine.
BecaplerminThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Becaplermin.
BeraprostThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Beraprost.
BetaxololThe metabolism of Ibrutinib can be decreased when combined with Betaxolol.
BevacizumabBevacizumab may increase the cardiotoxic activities of Ibrutinib.
BexaroteneThe serum concentration of Ibrutinib can be decreased when it is combined with Bexarotene.
BivalirudinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Bivalirudin.
BoceprevirThe serum concentration of Ibrutinib can be increased when it is combined with Boceprevir.
BortezomibThe serum concentration of Ibrutinib can be increased when it is combined with Bortezomib.
BosentanThe serum concentration of Ibrutinib can be decreased when it is combined with Bosentan.
BupropionThe metabolism of Ibrutinib can be decreased when combined with Bupropion.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Ibrutinib.
CangrelorThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Cangrelor.
CarbamazepineThe serum concentration of Ibrutinib can be decreased when it is combined with Carbamazepine.
CelecoxibThe metabolism of Ibrutinib can be decreased when combined with Celecoxib.
CeritinibThe serum concentration of Ibrutinib can be increased when it is combined with Ceritinib.
CertoparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Certoparin.
ChloroquineThe metabolism of Ibrutinib can be decreased when combined with Chloroquine.
ChlorpromazineThe metabolism of Ibrutinib can be decreased when combined with Chlorpromazine.
CholecalciferolThe metabolism of Ibrutinib can be decreased when combined with Cholecalciferol.
CilostazolThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Cilostazol.
CimetidineThe metabolism of Ibrutinib can be decreased when combined with Cimetidine.
CinacalcetThe metabolism of Ibrutinib can be decreased when combined with Cinacalcet.
CitalopramThe metabolism of Ibrutinib can be decreased when combined with Citalopram.
Citric AcidThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Citric Acid.
ClarithromycinThe serum concentration of Ibrutinib can be increased when it is combined with Clarithromycin.
ClemastineThe serum concentration of Ibrutinib can be increased when it is combined with Clemastine.
ClobazamThe metabolism of Ibrutinib can be decreased when combined with Clobazam.
ClomipramineThe metabolism of Ibrutinib can be decreased when combined with Clomipramine.
ClopidogrelThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Clopidogrel.
ClotrimazoleThe serum concentration of Ibrutinib can be increased when it is combined with Clotrimazole.
ClozapineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Clozapine.
ClozapineThe metabolism of Ibrutinib can be decreased when combined with Clozapine.
CobicistatThe serum concentration of Ibrutinib can be increased when it is combined with Cobicistat.
CocaineThe metabolism of Ibrutinib can be decreased when combined with Cocaine.
ConivaptanThe serum concentration of Ibrutinib can be increased when it is combined with Conivaptan.
CrizotinibThe serum concentration of Ibrutinib can be increased when it is combined with Crizotinib.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Ibrutinib.
CyclosporineThe serum concentration of Ibrutinib can be increased when it is combined with Cyclosporine.
Dabigatran etexilateThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dabigatran etexilate.
DabrafenibThe serum concentration of Ibrutinib can be decreased when it is combined with Dabrafenib.
DalteparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dalteparin.
DanaparoidThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Danaparoid.
DarifenacinThe metabolism of Ibrutinib can be decreased when combined with Darifenacin.
DarunavirThe serum concentration of Ibrutinib can be increased when it is combined with Darunavir.
DasatinibThe serum concentration of Ibrutinib can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Ibrutinib can be decreased when it is combined with Deferasirox.
DefibrotideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Defibrotide.
DelavirdineThe serum concentration of Ibrutinib can be increased when it is combined with Delavirdine.
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Ibrutinib.
DesipramineThe metabolism of Ibrutinib can be decreased when combined with Desipramine.
DesirudinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Desirudin.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Ibrutinib.
DexamethasoneThe serum concentration of Ibrutinib can be decreased when it is combined with Dexamethasone.
DextranThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dextran.
Dextran 40The risk or severity of adverse effects can be increased when Ibrutinib is combined with Dextran 40.
Dextran 70The risk or severity of adverse effects can be increased when Ibrutinib is combined with Dextran 70.
Dextran 75The risk or severity of adverse effects can be increased when Ibrutinib is combined with Dextran 75.
DicoumarolThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dicoumarol.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Ibrutinib.
DigoxinDigoxin may decrease the cardiotoxic activities of Ibrutinib.
DihydroergotamineThe serum concentration of Ibrutinib can be increased when it is combined with Dihydroergotamine.
DiltiazemThe serum concentration of Ibrutinib can be increased when it is combined with Diltiazem.
DiphenhydramineThe metabolism of Ibrutinib can be decreased when combined with Diphenhydramine.
DipyridamoleThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dipyridamole.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Ibrutinib.
DoxycyclineThe serum concentration of Ibrutinib can be increased when it is combined with Doxycycline.
DronedaroneThe serum concentration of Ibrutinib can be increased when it is combined with Dronedarone.
DuloxetineThe metabolism of Ibrutinib can be decreased when combined with Duloxetine.
Edetic AcidThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Edetic Acid.
EdoxabanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Edoxaban.
EfavirenzThe serum concentration of Ibrutinib can be decreased when it is combined with Efavirenz.
EliglustatThe metabolism of Ibrutinib can be decreased when combined with Eliglustat.
EnoxaparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Enoxaparin.
EnzalutamideThe serum concentration of Ibrutinib can be decreased when it is combined with Enzalutamide.
EpinastineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Epinastine.
EpoprostenolThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Epoprostenol.
EptifibatideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Eptifibatide.
ErythromycinThe serum concentration of Ibrutinib can be increased when it is combined with Erythromycin.
Eslicarbazepine acetateThe serum concentration of Ibrutinib can be decreased when it is combined with Eslicarbazepine acetate.
Ethyl biscoumacetateThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ethyl biscoumacetate.
EtravirineThe serum concentration of Ibrutinib can be decreased when it is combined with Etravirine.
FingolimodIbrutinib may increase the immunosuppressive activities of Fingolimod.
FluconazoleThe serum concentration of Ibrutinib can be increased when it is combined with Fluconazole.
FluoxetineThe metabolism of Ibrutinib can be decreased when combined with Fluoxetine.
FluvoxamineThe serum concentration of Ibrutinib can be increased when it is combined with Fluvoxamine.
Fondaparinux sodiumThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Fondaparinux sodium.
FosamprenavirThe serum concentration of Ibrutinib can be increased when it is combined with Fosamprenavir.
FosaprepitantThe serum concentration of Ibrutinib can be increased when it is combined with Fosaprepitant.
FosphenytoinThe serum concentration of Ibrutinib can be decreased when it is combined with Fosphenytoin.
Fusidic AcidThe serum concentration of Ibrutinib can be increased when it is combined with Fusidic Acid.
HaloperidolThe metabolism of Ibrutinib can be decreased when combined with Haloperidol.
HeparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Heparin.
HirulogThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Hirulog.
IbudilastThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ibudilast.
Icosapent ethylThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Icosapent ethyl.
IdelalisibThe serum concentration of Ibrutinib can be increased when it is combined with Idelalisib.
IfenprodilThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ifenprodil.
IloprostThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Iloprost.
ImatinibThe serum concentration of Ibrutinib can be increased when it is combined with Imatinib.
ImipramineThe metabolism of Ibrutinib can be decreased when combined with Imipramine.
IndinavirThe serum concentration of Ibrutinib can be increased when it is combined with Indinavir.
IsavuconazoniumThe serum concentration of Ibrutinib can be increased when it is combined with Isavuconazonium.
IsoniazidThe metabolism of Ibrutinib can be decreased when combined with Isoniazid.
IsradipineThe serum concentration of Ibrutinib can be increased when it is combined with Isradipine.
ItraconazoleThe serum concentration of Ibrutinib can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Ibrutinib can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of Ibrutinib can be increased when it is combined with Ketoconazole.
LeflunomideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Leflunomide.
LepirudinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Lepirudin.
LopinavirThe serum concentration of Ibrutinib can be increased when it is combined with Lopinavir.
LorcaserinThe metabolism of Ibrutinib can be decreased when combined with Lorcaserin.
LovastatinThe serum concentration of Ibrutinib can be increased when it is combined with Lovastatin.
LuliconazoleThe serum concentration of Ibrutinib can be increased when it is combined with Luliconazole.
LumefantrineThe metabolism of Ibrutinib can be decreased when combined with Lumefantrine.
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Ibrutinib.
MethadoneThe metabolism of Ibrutinib can be decreased when combined with Methadone.
MethotrimeprazineThe metabolism of Ibrutinib can be decreased when combined with Methotrimeprazine.
MetoprololThe metabolism of Ibrutinib can be decreased when combined with Metoprolol.
MifepristoneThe serum concentration of Ibrutinib can be increased when it is combined with Mifepristone.
MilrinoneThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Milrinone.
MirabegronThe metabolism of Ibrutinib can be decreased when combined with Mirabegron.
MitotaneThe serum concentration of Ibrutinib can be decreased when it is combined with Mitotane.
ModafinilThe serum concentration of Ibrutinib can be decreased when it is combined with Modafinil.
NadroparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Nadroparin.
NafcillinThe serum concentration of Ibrutinib can be decreased when it is combined with Nafcillin.
NatalizumabThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Natalizumab.
NCX 4016The risk or severity of adverse effects can be increased when Ibrutinib is combined with NCX 4016.
NefazodoneThe serum concentration of Ibrutinib can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Ibrutinib can be increased when it is combined with Nelfinavir.
NetupitantThe serum concentration of Ibrutinib can be increased when it is combined with Netupitant.
NevirapineThe serum concentration of Ibrutinib can be increased when it is combined with Nevirapine.
NicardipineThe metabolism of Ibrutinib can be decreased when combined with Nicardipine.
NilotinibThe serum concentration of Ibrutinib can be increased when it is combined with Nilotinib.
NimesulideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Nimesulide.
OlaparibThe serum concentration of Ibrutinib can be increased when it is combined with Olaparib.
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Ibrutinib.
OsimertinibThe serum concentration of Ibrutinib can be increased when it is combined with Osimertinib.
OtamixabanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Otamixaban.
OuabainOuabain may decrease the cardiotoxic activities of Ibrutinib.
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Ibrutinib.
PalbociclibThe serum concentration of Ibrutinib can be increased when it is combined with Palbociclib.
PanobinostatThe metabolism of Ibrutinib can be decreased when combined with Panobinostat.
ParoxetineThe metabolism of Ibrutinib can be decreased when combined with Paroxetine.
Peginterferon alfa-2bThe serum concentration of Ibrutinib can be decreased when it is combined with Peginterferon alfa-2b.
PentobarbitalThe serum concentration of Ibrutinib can be decreased when it is combined with Pentobarbital.
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Pentosan Polysulfate.
PentoxifyllineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Pentoxifylline.
PhenindioneThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Phenindione.
PhenobarbitalThe serum concentration of Ibrutinib can be decreased when it is combined with Phenobarbital.
PhenprocoumonThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Phenprocoumon.
PhenytoinThe serum concentration of Ibrutinib can be decreased when it is combined with Phenytoin.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Ibrutinib.
PosaconazoleThe serum concentration of Ibrutinib can be increased when it is combined with Posaconazole.
PrasugrelThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Prasugrel.
PrimidoneThe serum concentration of Ibrutinib can be decreased when it is combined with Primidone.
PromazineThe metabolism of Ibrutinib can be decreased when combined with Promazine.
Protein CThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Protein C.
ProtocatechualdehydeThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Protocatechualdehyde.
QuinidineThe metabolism of Ibrutinib can be decreased when combined with Quinidine.
QuinineThe metabolism of Ibrutinib can be decreased when combined with Quinine.
Rabies vaccineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Rabies vaccine.
RanolazineThe serum concentration of Ibrutinib can be increased when it is combined with Ranolazine.
ResveratrolThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Resveratrol.
ReviparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Reviparin.
RidogrelThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ridogrel.
RifabutinThe serum concentration of Ibrutinib can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Ibrutinib can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Ibrutinib can be decreased when it is combined with Rifapentine.
RitonavirThe serum concentration of Ibrutinib can be increased when it is combined with Ritonavir.
RivaroxabanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Rivaroxaban.
RoflumilastRoflumilast may increase the immunosuppressive activities of Ibrutinib.
RolapitantThe metabolism of Ibrutinib can be decreased when combined with Rolapitant.
RopiniroleThe metabolism of Ibrutinib can be decreased when combined with Ropinirole.
SaquinavirThe serum concentration of Ibrutinib can be increased when it is combined with Saquinavir.
SCH-530348The risk or severity of adverse effects can be increased when Ibrutinib is combined with SCH-530348.
SertralineThe metabolism of Ibrutinib can be decreased when combined with Sertraline.
SevofluraneThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Sevoflurane.
SildenafilThe serum concentration of Ibrutinib can be increased when it is combined with Sildenafil.
SiltuximabThe serum concentration of Ibrutinib can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Ibrutinib can be increased when it is combined with Simeprevir.
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Ibrutinib.
SRT501The risk or severity of adverse effects can be increased when Ibrutinib is combined with SRT501.
St. John's WortThe serum concentration of Ibrutinib can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Ibrutinib can be increased when it is combined with Stiripentol.
SulfisoxazoleThe serum concentration of Ibrutinib can be increased when it is combined with Sulfisoxazole.
SulodexideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Sulodexide.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Ibrutinib.
TelaprevirThe serum concentration of Ibrutinib can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Ibrutinib can be increased when it is combined with Telithromycin.
TerbinafineThe metabolism of Ibrutinib can be decreased when combined with Terbinafine.
TesmilifeneThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Tesmilifene.
ThioridazineThe metabolism of Ibrutinib can be decreased when combined with Thioridazine.
TiclopidineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ticlopidine.
TiclopidineThe serum concentration of Ibrutinib can be increased when it is combined with Ticlopidine.
TipranavirThe metabolism of Ibrutinib can be decreased when combined with Tipranavir.
TirofibanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Tirofiban.
TocilizumabThe serum concentration of Ibrutinib can be decreased when it is combined with Tocilizumab.
TofacitinibIbrutinib may increase the immunosuppressive activities of Tofacitinib.
TranilastThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Tranilast.
TranylcypromineThe metabolism of Ibrutinib can be decreased when combined with Tranylcypromine.
TrapidilThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Trapidil.
TrastuzumabTrastuzumab may increase the neutropenic activities of Ibrutinib.
TriflusalThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Triflusal.
VenlafaxineThe serum concentration of Ibrutinib can be increased when it is combined with Venlafaxine.
VerapamilThe serum concentration of Ibrutinib can be increased when it is combined with Verapamil.
Vitamin EVitamin E may increase the antiplatelet activities of Ibrutinib.
VorapaxarThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Vorapaxar.
VoriconazoleThe serum concentration of Ibrutinib can be increased when it is combined with Voriconazole.
WarfarinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Warfarin.
XimelagatranThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ximelagatran.
ZiprasidoneThe serum concentration of Ibrutinib can be increased when it is combined with Ziprasidone.
Food Interactions
  • Administration with food increases ibrutinib exposure approximately 2-fold compared with administration after overnight fasting.

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 September 25, 2016 03:14