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Identification
NameIbrutinib
Accession NumberDB09053
TypeSmall Molecule
GroupsApproved
Description

Ibrutinib 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
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
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.
AcenocoumarolThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Acetylsalicylic acid.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Ibrutinib.
AnagrelideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Anagrelide.
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.
ArgatrobanThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Argatroban.
AtazanavirThe serum concentration of Ibrutinib can be increased when it is combined with Atazanavir.
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.
BosentanThe serum concentration of Ibrutinib can be decreased when it is combined with Bosentan.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Ibrutinib.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it 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.
CeritinibThe serum concentration of Ibrutinib can be increased when it is combined with Ceritinib.
CilostazolThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Cilostazol.
CitalopramThe risk or severity of adverse effects can be increased when Ibrutinib is 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.
ClopidogrelThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Clopidogrel.
ClozapineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Clozapine.
CobicistatThe serum concentration of Ibrutinib can be increased when it is combined with Cobicistat.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Ibrutinib.
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.
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Ibrutinib.
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.
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.
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.
DesirudinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Desirudin.
DesvenlafaxineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Desvenlafaxine.
DexamethasoneThe serum concentration of Ibrutinib can be decreased when it is combined with Dexamethasone.
DiclofenacThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Diclofenac.
DicoumarolThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dicoumarol.
DiflunisalThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Diflunisal.
DiltiazemThe serum concentration of Ibrutinib can be increased when it is combined with Diltiazem.
DipyridamoleThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Dipyridamole.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Ibrutinib.
DronedaroneThe serum concentration of Ibrutinib can be increased when it is combined with Dronedarone.
DuloxetineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Duloxetine.
Edetic AcidThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Edetic Acid.
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Ibrutinib.
EfavirenzThe serum concentration of Ibrutinib can be decreased when it is combined with Efavirenz.
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.
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.
EscitalopramThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Escitalopram.
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.
EtodolacThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Etodolac.
EtravirineThe serum concentration of Ibrutinib can be decreased when it is combined with Etravirine.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Ibrutinib.
FenoprofenThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Fenoprofen.
FloctafenineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Floctafenine.
FluconazoleThe serum concentration of Ibrutinib can be increased when it is combined with Fluconazole.
FluoxetineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Fluoxetine.
FlurbiprofenThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Flurbiprofen.
FluvoxamineThe risk or severity of adverse effects can be increased when Ibrutinib 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.
HeparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Heparin.
IbuprofenThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ibuprofen.
IcosapentIcosapent may increase the antiplatelet activities of Ibrutinib.
Icosapent ethylIcosapent ethyl may increase the antiplatelet activities of Ibrutinib.
IdelalisibThe serum concentration of Ibrutinib can be increased when it is combined with Idelalisib.
ImatinibThe serum concentration of Ibrutinib can be increased when it is combined with Imatinib.
IndinavirThe serum concentration of Ibrutinib can be increased when it is combined with Indinavir.
IndomethacinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Indomethacin.
IsavuconazoniumThe serum concentration of Ibrutinib can be increased when it is combined with Isavuconazonium.
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.
KetoprofenThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ketoprofen.
KetorolacThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ketorolac.
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Ibrutinib.
LeflunomideThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Leflunomide.
LevomilnacipranThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Levomilnacipran.
LuliconazoleThe serum concentration of Ibrutinib can be increased when it is combined with Luliconazole.
Mefenamic acidThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Mefenamic acid.
MeloxicamThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Meloxicam.
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Ibrutinib.
MifepristoneThe serum concentration of Ibrutinib can be increased when it is combined with Mifepristone.
MilnacipranThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Milnacipran.
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.
NabumetoneThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Nabumetone.
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.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Ibrutinib.
NaproxenThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Naproxen.
NatalizumabThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Natalizumab.
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.
NilotinibThe serum concentration of Ibrutinib can be increased when it is combined with Nilotinib.
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Ibrutinib.
Omega-3-acid ethyl estersOmega-3-acid ethyl esters may increase the antiplatelet activities of Ibrutinib.
OxaprozinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Oxaprozin.
PalbociclibThe serum concentration of Ibrutinib can be increased when it is combined with Palbociclib.
ParoxetineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Paroxetine.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Ibrutinib.
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.
PiroxicamThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Piroxicam.
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.
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Ibrutinib.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Ibrutinib.
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.
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Ibrutinib.
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.
SaquinavirThe serum concentration of Ibrutinib can be increased when it is combined with Saquinavir.
SertralineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Sertraline.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Ibrutinib.
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.
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.
SulindacThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Sulindac.
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.
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Tiaprofenic acid.
TicagrelorThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ticagrelor.
TiclopidineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Ticlopidine.
TinzaparinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Tinzaparin.
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.
TolmetinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Tolmetin.
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Ibrutinib.
TrastuzumabTrastuzumab may increase the neutropenic activities of Ibrutinib.
TreprostinilThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Treprostinil.
VenlafaxineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Venlafaxine.
VerapamilThe serum concentration of Ibrutinib can be increased when it is combined with Verapamil.
VilazodoneThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Vilazodone.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Ibrutinib.
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.
VortioxetineThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Vortioxetine.
WarfarinThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Warfarin.
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 June 28, 2016 02:49