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Product Details:

  • Product Name: Ibrutinib
  • CAS #: 936563-96-1
  • Mode 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, 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.

  • Pharmacodynamics:

    In 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).

  • 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.

  • ATC: L01XE27
  • DrugBank: DB09053
  • Formula: C25-H24-N6-O2
  • Molecular Mass: 440.5046
  • Synonyms: 2-Propen-1-one, 1-((3R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo(3,4-d)pyrimidin-1-yl)-1-piperidinyl)-, CRA-032765, Ibrutinib, Pc-32765, PCI 32765, PCI32765, UNII-1X70OSD4VX
  • SMILES: C=CC(=O)N1CCCC(C1)[n@]2c3c(c(n2)c4ccc(cc4)Oc5ccccc5)c(ncn3)N
  • InChl: 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)
  • General Reference:

    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
    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
    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 14C 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.
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