An internal standard for the quantification of ibrutinib
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Unlabeled Version(s)
16274Ibrutinib
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Ibrutinib-d5

Item No. 22561

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[(3R)-3-[4-amino-3-[4-(phenoxy-2,3,4,5,6-d5)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl]-2-propen-1-one
CAS Number
1553977-17-5
Molecular Formula
C25H19D5N6O2
Formula Weight
445.5
Purity
≥99% deuterated forms (d1-d5)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 0.25 mg/ml
SMILES
O=C(C=C)N1C[C@H](N2C(N=CN=C3N)=C3C(C4=CC=C(OC5=C([2H])C([2H])=C([2H])C([2H])=C5[2H])C=C4)=N2)CCC1
InChi Code
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/i3D,4D,5D,8D,9D
InChi Key
XYFPWWZEPKGCCK-OZUAZJOXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $148

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    Product Description

    Ibrutinib-d5 is intended for use as an internal standard for the quantification of ibrutinib (Item No. 16274) by GC- or LC-MS. Ibrutinib is an irreversible inhibitor of Bruton’s tyrosine kinase (BTK; IC50 = 0.5 nM) that selectively blocks B cell activation, promoting apoptosis and preventing homing to the protective tumor microenvironment, at concentrations that do not affect T cell receptor signaling (1,000-fold more potent).1,2 It has been reported to inhibit autophosphorylation of BTK (IC50 = 11 nM), phosphorylation of PLCγ (IC50 = 29 nM), a substrate of BTK, and phosphorylation of ERK (IC50 = 13 nM), a further downstream kinase.1 Formulations containing it have been examined clinically for the treatment of diseases associated with B cell antigen receptor signaling, including mantle cell lymphoma, chronic lymphocytic leukemia, and non-Hodgkin lymphoma.3,1,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Honigberg, L.A., Smith, A.M., Sirisawad, M., et al. The Bruton tyrosine kinase inhibitor PCI-32765 blocks B-cell activation and is efficacious in models of autoimmune disease and B-cell malignancy. Proc. Natl. Acad. Sci. USA 107(29), 13075-13080 (2010).

    2. Herman, S.E.M., Gordon, A.L., Hertlein, E., et al. Bruton tyrosine kinase represents a promising therapeutic target for treatment of chronic lymphocytic leukemia and is effectively targeted by PCI-32765. Blood 117(23), 6287-6296 (2011).

    3. Leslie, L.A., and Younes, A. Targeting oncogenic and epigenetic survival pathways in lymphoma. Leuk. Lymphoma. 54(11), 2365-2376 (2013).

    4. Wu, M., Akinleye, A., and Zhu, X. Novel agents for chronic lymphocytic leukemia. J. Hematol. Oncol. 6, 36 (2013).