Identification
- Summary
Ibrutinib is an antineoplastic agent used to treat chronic lymphocytic leukemia, mantle cell lymphoma, and Waldenstrom's Macroglobulinemia.
- Brand Names
- Imbruvica
- Generic Name
- Ibrutinib
- DrugBank Accession Number
- DB09053
- Background
Ibrutinib is a small molecule that acts as an irreversible potent inhibitor of Burton's tyrosine kinase. It is designated as a targeted covalent drug and presented as a promising activity in B-cell malignancies in clinical trials.4 Ibrutinib was developed by Pharmacyclics Inc and was first approved by the FDA in November 2013 for the treatment of mantle cell lymphoma (MCL) under accelerated approval;16 however, in April 2023, the drug manufacturer withdrew the accelerated approvals for ibrutinib in the US.21
Ibrutinib was approved by the EMA in October 2014 19 and by Health Canada in November 2014.20 It is currently approved for the treatment of various conditions, such as chronic lymphocytic leukemia (CLL), Waldenström's Macroglobulinemia, and chronic graft versus host disease (cGVHD) in August 2017.16 Notably, ibrutinib became the first FDA-approved cGVHD treatment for children in August 2017.18
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Ibrutinib (DB09053)
- Weight
- Average: 440.507
Monoisotopic: 440.196074037 - Chemical Formula
- C25H24N6O2
- 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
- Ibrutinib
- External IDs
- CRA-032765
- PC-32765
- PCI 32765
- PCI-32765
- PCI-32765-00
Pharmacology
- Indication
Ibrutinib is indicated for the treatment of the following conditions.
Chronic lymphocytic leukemia (CLL)/small lymphocytic lymphoma (SLL)
- In the US, it is used in adult patients with or without 17p deletion.17,19
- In Europe and Canada, it is used as a single agent or combined with rituximab, obinutuzumab, or venetoclax in previously untreated CLL patients. In patients who have received at least one prior therapy, it is used as a single agent or in combination with bendamustine and rituximab.19,20
Waldenström's macroglobulinemia
- It is used alone 17,19,20 or with rituximab.19,20
- In Europe, it is approved for patients who have received at least one prior therapy or in first-line treatment for patients unsuitable for chemoimmunotherapy.19
Chronic graft-versus-host disease (cGVHD)
- In the US, it is approved in patients aged one year and older after the prior failure of one or more lines of systemic therapy.17
- In Canada, it is approved in adults with steroid-dependent or refractory cGVHD.20
Mantle cell lymphoma (MCL)
- In Europe and Canada, ibrutinib is also indicated to treat relapsed or refractory MCL in adults.19,20
Marginal zone lymphoma (MZL)
- In Canada, it is approved for adults who require systemic therapy and have received at least one prior anti-CD20-based therapy.20
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Chronic graft-versus-host disease •••••••••••• ••••••• •• •• ••••• ••• ••••• •••••••• ••••••• •••••••• ••••••••••• •••••• Used in combination to treat Chronic lymphocytic leukemia Regimen in combination with: Rituximab (DB00073) •••••••••••• ••••• •• ••••• ••• ••••• ••••••• •••••••• •••••• Used in combination to treat Chronic lymphocytic leukemia Regimen in combination with: Bendamustine (DB06769) •••••••••••• ••••• •• ••••• ••• ••••• ••••••• •••••••• •••••• Used in combination to treat Chronic lymphocytic leukemia Regimen in combination with: Venetoclax (DB11581) •••••••••••• ••••• ••••••••• ••••• •••••••• •••••• Used in combination to treat Chronic lymphocytic leukemia Regimen in combination with: Obinutuzumab (DB08935) •••••••••••• ••••• ••••••••• ••••• •••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
In vitro studies have shown an induction of CLL cell apoptosis even in presence of prosurvival factors. It has also been reported an inhibition of CLL cell survival and proliferation as well as an impaired in cell migration and a reduction in the secretion of chemokines such as CCL3 and CCL4. The latter effect has been shown to produce regression in xenograft mouse models.6
Clinical studies for relapsed/refractory CLL in phase I and II showed an approximate 71% of overall response rate.7,8. In the case of relapsed/refractory mantle cell lymphoma, approximately 70% of the tested patients presented a partial or complete response.7,9. In clinical trials for relapsed/refractory diffuse large B-cell lymphoma, a partial response was found in between 15-20% of the patients studied; while for patients with relapsed/refractory Waldenstrom's macroglobulinemia, a partial response was observed in over 75% of the patients tested. Finally, for patients with relapsed/refractory follicular lymphoma, a partial to complete response was obtained in approximately 54% of the patients.7
- Mechanism of action
Ibrutinib is an inhibitor of Bruton’s tyrosine kinase (BTK). It forms a covalent bond with a cysteine residue in the active site of BTK (Cys481), leading to its inhibition. The inhibition of BTK plays a role in the B-cell receptor signaling and thus, the presence of ibrutinib prevents the phosphorylation of downstream substrates such as PLC-γ.6
Target Actions Organism ATyrosine-protein kinase BTK inhibitorHumans - Absorption
Ibrutinib is rapidly absorbed after oral administration and it presents a Cmax, tmax and AUC of approximately 35 ng/ml, 1-2 hour and 953 mg.h/ml respectively.11
- Volume of distribution
The volume of distribution at steady-state of ibrutinib is in approximately 10,000 L.11
- Protein binding
Irreversible plasma protein binding increases gradually over time and reaches 25% of the administered dose 8 hours after initial administration. From the plasma proteins, ibrutinib has been shown to be mainly bound to albumin and to bind to α1 AGP.3 The irreversible protein binding of ibrutinib to plasma proteins can account for 97.3% of the administered dose.11
- Metabolism
Three metabolic pathways have been identified according to the possible metabolites. These pathways are the hydroxylation of the phenyl group (M35), the opening of the piperidine with a reduction of the primary alcohol (M34) and the oxidation to a carboxylic acid and epoxidation of the ethylene followed by a hydrolysis to the formation of dihydrodiol (PCI-45227). The latter metabolite presents also 15 times lower inhibitory activity against BTK. The metabolism of ibrutinib is mainly performed by CYP3A5 and CYP3A4. and in a minor extent it is seen to be performed by CYP2D6.3
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- Route of elimination
The cumulative excretion of ibrutinib in urine is of about 7.8% of the administered dose and most of this excretion is found during the first 24 hours after administration. In feces, the cumulative excretion accounts for 80% of the administered dose and the excretion occurs within 48 hours of the initial administration. The total excretion of ibrutinib during the first 168 hours after initial administration accounts for 88.5% of the administered dose.3
- Half-life
The elimination half-life of ibrutinib is of approximately 4-6 hours.11
- Clearance
In patients with normal renal function, the clearance rate is in the range of 112-159 ml/min.3
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Ibrutinib was not showed to present a mutagenic potential in bacterial assays, nor clastogenic in chromosome aberration assays in mammalian cells or in bone marrow micronucleus assays in mice. Carcinogenicity or effects on fertility have not been determined.16
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Ibrutinib can be increased when it is combined with Abametapir. Abatacept The metabolism of Ibrutinib can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Ibrutinib is combined with Abciximab. Abiraterone The metabolism of Ibrutinib can be decreased when combined with Abiraterone. Acalabrutinib The metabolism of Ibrutinib can be decreased when combined with Acalabrutinib. - Food Interactions
- Avoid grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum concentration of ibrutinib.
- Avoid St. John's Wort. This herb induces CYP3A4 and may reduce the serum concentration of ibrutinib.
- Take at the same time every day.
- Take with a full glass of water.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Imbruvica Tablet, film coated 280 mg/1 Oral Pharmacyclics LLC 2018-02-16 Not applicable US 
Imbruvica Tablet, film coated 560 mg Oral Janssen Cilag International Nv 2021-02-11 Not applicable EU 
Imbruvica Capsule 140 mg/1 Oral Pharmacyclics LLC 2013-11-13 Not applicable US Imbruvica Tablet, film coated 280 mg Oral Janssen Cilag International Nv 2021-02-10 Not applicable EU Imbruvica Tablet 280 mg Oral Janssen Pharmaceuticals Not applicable Not applicable Canada 
Categories
- ATC Codes
- L01EL01 — Ibrutinib
- Drug Categories
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Bruton's tyrosine kinase (BTK) inhibitors
- Cancer immunotherapy
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 Substrates
- Enzyme Inhibitors
- Heterocyclic Compounds, Fused-Ring
- Immunosuppressive Agents
- Immunotherapy
- Kinase Inhibitor
- Myelosuppressive Agents
- Protein Kinase Inhibitors
- Purines
- Tyrosine Kinase Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylethers
- Direct Parent
- Diphenylethers
- Alternative Parents
- Diarylethers / Phenylpyrazoles / Pyrazolo[3,4-d]pyrimidines / N-acylpiperidines / Phenol ethers / Phenoxy compounds / Aminopyrimidines and derivatives / Imidolactams / Heteroaromatic compounds / Tertiary carboxylic acid amides show 8 more
- Substituents
- Acrylic acid or derivatives / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Carbonyl group / Carboxamide group / Carboxylic acid derivative show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- aromatic ether, N-acylpiperidine, aromatic amine, pyrazolopyrimidine, acrylamides (CHEBI:76612)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 1X70OSD4VX
- CAS number
- 936563-96-1
- InChI Key
- XYFPWWZEPKGCCK-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
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Berglof A, Hamasy A, Meinke S, Palma M, Krstic A, Mansson R, Kimby E, Osterborg A, Smith CI: Targets for Ibrutinib Beyond B Cell Malignancies. Scand J Immunol. 2015 Sep;82(3):208-17. doi: 10.1111/sji.12333. [Article]
- Sellner L, Denzinger S, Dietrich S, Glimm H, Merkel O, Dreger P, Zenz T: What do we do with chronic lymphocytic leukemia with 17p deletion? Curr Hematol Malig Rep. 2013 Mar;8(1):81-90. doi: 10.1007/s11899-012-0143-0. [Article]
- Davids MS, Brown JR: Ibrutinib: a first in class covalent inhibitor of Bruton's tyrosine kinase. Future Oncol. 2014 May;10(6):957-67. doi: 10.2217/fon.14.51. [Article]
- Advani RH, Buggy JJ, Sharman JP, Smith SM, Boyd TE, Grant B, Kolibaba KS, Furman RR, Rodriguez S, Chang BY, Sukbuntherng J, Izumi R, Hamdy A, Hedrick E, Fowler NH: Bruton tyrosine kinase inhibitor ibrutinib (PCI-32765) has significant activity in patients with relapsed/refractory B-cell malignancies. J Clin Oncol. 2013 Jan 1;31(1):88-94. doi: 10.1200/JCO.2012.42.7906. Epub 2012 Oct 8. [Article]
- Byrd JC, Furman RR, Coutre SE, Flinn IW, Burger JA, Blum KA, Grant B, Sharman JP, Coleman M, Wierda WG, Jones JA, Zhao W, Heerema NA, Johnson AJ, Sukbuntherng J, Chang BY, Clow F, Hedrick E, Buggy JJ, James DF, O'Brien S: Targeting BTK with ibrutinib in relapsed chronic lymphocytic leukemia. N Engl J Med. 2013 Jul 4;369(1):32-42. doi: 10.1056/NEJMoa1215637. Epub 2013 Jun 19. [Article]
- Wang ML, Rule S, Martin P, Goy A, Auer R, Kahl BS, Jurczak W, Advani RH, Romaguera JE, Williams ME, Barrientos JC, Chmielowska E, Radford J, Stilgenbauer S, Dreyling M, Jedrzejczak WW, Johnson P, Spurgeon SE, Li L, Zhang L, Newberry K, Ou Z, Cheng N, Fang B, McGreivy J, Clow F, Buggy JJ, Chang BY, Beaupre DM, Kunkel LA, Blum KA: Targeting BTK with ibrutinib in relapsed or refractory mantle-cell lymphoma. N Engl J Med. 2013 Aug 8;369(6):507-16. doi: 10.1056/NEJMoa1306220. Epub 2013 Jun 19. [Article]
- Authors unspecified: Ibrutinib. Aust Prescr. 2015 Oct;38(5):178-80. Epub 2015 Jun 15. [Article]
- Bronson J., Black A., Dhar M., Ellsworth B. and Merritt R. (2014). Annual reports in medicinal chemistry. Elsevier.
- FDA: Ibrutinib cGVHD approval [Link]
- Canadian cancer society [Link]
- National Cancer Institute [Link]
- American Cancer Society [Link]
- FDA Approved Drug Products: Imbruvica (ibrutinib) oral capsules [Link]
- FDA Approved Drug Products: IMBRUVICA (ibrutinib) capsules, tablets, or suspension, for oral use (August 2022) [Link]
- Janssen Biotech: IMBRUVICA for Previously Treated cGVHD in Children 1 Year and Older [Link]
- EMA Approved Drug Products: Imbruvica (ibrutinib) Oral Capsules or Tablets [Link]
- Health Canada Approved Drug Products: IMBRUVICA (ibrutinib) Oral Capsules or Tablets [Link]
- BioSpace: AbbVie, J&J Pull Two Accelerated Approvals for Imbruvica [Link]
- External Links
- KEGG Drug
- D10223
- PubChem Compound
- 24821094
- PubChem Substance
- 310264995
- ChemSpider
- 26637187
- BindingDB
- 50357312
- 1442981
- ChEBI
- 76612
- ChEMBL
- CHEMBL1873475
- ZINC
- ZINC000035328014
- PharmGKB
- PA166121346
- PDBe Ligand
- 1E8
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Ibrutinib
- PDB Entries
- 4ifg / 4rz7 / 5p9i / 5yu9 / 6l8l / 6yg2 / 6yz4
- FDA label
- Download (579 KB)
- MSDS
- Download (24.9 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Waldenström's Macroglobulinemia (WM) 1 4 Completed Other B-Cell Chronic Lymphocytic Leukemia / Mantle Cell Lymphoma (MCL) 1 4 Enrolling by Invitation Treatment B-Cell Leukemia / B-Cell Lymphoma / Graft-versus-host Disease (GVHD) / Non-Hodgkin's Lymphoma (NHL) / Solid Tumors 1 3 Active Not Recruiting Treatment Anemia / Chronic Lymphocytic Leukemia / Small Lymphocytic Lymphoma 1 3 Active Not Recruiting Treatment B-Cell Chronic Lymphocytic Leukemia 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral Capsule Oral 140 mg/1 Capsule Oral 140.000 mg Capsule Oral 70 mg/1 Suspension Oral 70 mg / mL Suspension Oral 70 mg/1mL Tablet Oral 140 mg Tablet Oral 140.00 mg Tablet Oral 280 mg Tablet Oral 420 mg Tablet Oral 560 mg Tablet, film coated Oral 140 Mg Tablet, film coated Oral 140 mg/1 Tablet, film coated Oral 280 mg/1 Tablet, film coated Oral 420 mg/1 Tablet, film coated Oral 560 mg/1 Tablet, film coated Oral 280 mg Tablet, film coated Oral 420 mg Tablet, film coated Oral 560 mg Tablet, coated Oral 140 mg Tablet, coated Oral 420 mg Tablet, coated Oral 560 mg Capsule, coated Oral 140 mg Tablet, coated Oral 280 mg Capsule Oral 140 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8476284 Yes 2013-07-02 2027-06-28 US US8703780 Yes 2014-04-22 2027-06-28 US US8754090 Yes 2014-06-17 2031-12-03 US US8497277 Yes 2013-07-30 2027-06-28 US US9125889 Yes 2015-09-08 2031-12-03 US US8999999 Yes 2015-04-07 2031-12-03 US US8697711 Yes 2014-04-15 2027-06-28 US US8754091 Yes 2014-06-17 2027-06-28 US US9181257 Yes 2015-11-10 2027-06-28 US US8957079 Yes 2015-02-17 2027-06-28 US US8008309 Yes 2011-08-30 2028-05-13 US US8735403 Yes 2014-05-27 2027-06-28 US US9296753 Yes 2016-03-29 2034-04-30 US US7514444 Yes 2009-04-07 2027-06-28 US US9540382 Yes 2017-01-10 2034-02-18 US US8952015 Yes 2015-02-10 2027-06-28 US US9725455 Yes 2017-08-08 2033-12-03 US US9713617 Yes 2017-07-25 2033-12-03 US US9795604 Yes 2017-10-24 2035-04-24 US US9801883 Yes 2017-10-31 2031-12-03 US US9801881 Yes 2017-10-31 2031-12-03 US US9814721 Yes 2017-11-14 2031-12-03 US US8563563 Yes 2013-10-22 2027-10-26 US US9655857 Yes 2017-05-23 2036-09-03 US US10004746 Yes 2018-06-26 2031-12-03 US US10016435 Yes 2018-07-10 2031-12-03 US US10010507 Yes 2018-07-03 2036-09-03 US US10106548 Yes 2018-10-23 2033-12-03 US US10125140 Yes 2018-11-13 2033-12-03 US US10213386 Yes 2019-02-26 2036-09-03 US US10294232 Yes 2019-05-21 2033-12-03 US US10294231 Yes 2019-05-21 2033-12-03 US US10463668 Yes 2019-11-05 2035-04-24 US US10478439 Yes 2019-11-19 2031-12-03 US US10653696 Yes 2020-05-19 2031-12-03 US US10695350 Yes 2020-06-30 2035-04-24 US US10752634 Yes 2020-08-25 2033-12-03 US US10751342 Yes 2020-08-25 2031-12-03 US US10828259 Yes 2020-11-10 2036-09-03 US US10961251 Yes 2021-03-30 2033-12-03 US US11672803 No 2011-06-03 2031-06-03 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 149-158ºC FDA Imbruvica review. (2013) water solubility 0.003 mg/ml FDA Imbruvica review. (2013) logP 3.97 FDA Imbruvica review. (2013) pKa 3.74 FDA Imbruvica review. (2013) - Predicted Properties
Property Value Source Water Solubility 0.0203 mg/mL ALOGPS logP 2.76 ALOGPS logP 3.63 Chemaxon logS -4.3 ALOGPS pKa (Strongest Acidic) 19.7 Chemaxon pKa (Strongest Basic) 6.58 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 99.16 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 138.07 m3·mol-1 Chemaxon Polarizability 47.84 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0001900000-e86b828ac892243c45f9 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0000900000-2d94f53d3b7c2045897d Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000l-1009400000-d2f56d4a02e2b00d9173 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000l-6026900000-16d6ee72f7c7ad8d7728 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0ufu-0019400000-559c70f104ee3e739cf6 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9415100000-aeb255ae330fece1da44 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 196.38197 predictedDeepCCS 1.0 (2019) [M+H]+ 198.77754 predictedDeepCCS 1.0 (2019) [M+Na]+ 204.69006 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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 le...
- Gene Name
- BTK
- Uniprot ID
- Q06187
- Uniprot Name
- Tyrosine-protein kinase BTK
- Molecular Weight
- 76280.71 Da
References
- 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. [Article]
- Bond DA, Woyach JA: Targeting BTK in CLL: Beyond Ibrutinib. Curr Hematol Malig Rep. 2019 Jun;14(3):197-205. doi: 10.1007/s11899-019-00512-0. [Article]
- Thompson PA, Burger JA: Bruton's tyrosine kinase inhibitors: first and second generation agents for patients with Chronic Lymphocytic Leukemia (CLL). Expert Opin Investig Drugs. 2018 Jan;27(1):31-42. doi: 10.1080/13543784.2018.1404027. Epub 2017 Nov 15. [Article]
- McWilliams EM, Lucas CR, Chen T, Harrington BK, Wasmuth R, Campbell A, Rogers KA, Cheney CM, Mo X, Andritsos LA, Awan FT, Woyach J, Carson WE 3rd, Butchar J, Tridandapani S, Hertlein E, Castro CE, Muthusamy N, Byrd JC: Anti-BAFF-R antibody VAY-736 demonstrates promising preclinical activity in CLL and enhances effectiveness of ibrutinib. Blood Adv. 2019 Feb 12;3(3):447-460. doi: 10.1182/bloodadvances.2018025684. [Article]
- Castillo JJ, Treon SP: What is new in the treatment of Waldenstrom macroglobulinemia? Leukemia. 2019 Nov;33(11):2555-2562. doi: 10.1038/s41375-019-0592-8. Epub 2019 Oct 7. [Article]
- Zheng TJ, Lofurno ER, Melrose AR, Lakshmanan HHS, Pang J, Phillips KG, Fallon ME, Kohs TCL, Ngo ATP, Shatzel JJ, Hinds MT, McCarty OJT, Aslan JE: Assessment of the effects of Syk and BTK inhibitors on GPVI-mediated platelet signaling and function. Am J Physiol Cell Physiol. 2021 May 1;320(5):C902-C915. doi: 10.1152/ajpcell.00296.2020. Epub 2021 Mar 10. [Article]
- Kaliamurthi S, Selvaraj G, Selvaraj C, Singh SK, Wei DQ, Peslherbe GH: Structure-Based Virtual Screening Reveals Ibrutinib and Zanubrutinib as Potential Repurposed Drugs against COVID-19. Int J Mol Sci. 2021 Jun 30;22(13). pii: ijms22137071. doi: 10.3390/ijms22137071. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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 react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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 un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- 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. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- 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. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Not Available
- Specific Function
- Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Components:
References
- 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. [Article]
Drug created at May 07, 2015 19:33 / Updated at December 05, 2023 12:31