An internal standard for the quantification of imatinib
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Labeled Version(s)
13139Imatinib (mesylate)
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Imatinib-d3

Item No. 18257

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[[4-(methyl-d3)-1-piperazinyl]methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide
CAS Number
1134803-18-1
Synonyms
  • Genfatinib-d3
Molecular Formula
C29H28D3N7O
Formula Weight
496.6
Purity
≥99% deuterated forms (d1-d3)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly solubleMethanol: slightly soluble
SMILES
O=C(NC1=CC=C(C)C(NC2=NC(C3=CC=CN=C3)=CC=N2)=C1)C(C=C4)=CC=C4CN5CCN(C([2H])([2H])[2H])CC5
InChi Code
InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)/i2D3
InChi Key
KTUFNOKKBVMGRW-BMSJAHLVSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $112

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    1 mg

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    Product Description

    Imatinib-d3 is intended for use as an internal standard for the quantification of imatinib (Item No. 13139) by GC- or LC-MS. Imatinib is an inhibitor of the receptor tyrosine kinases c-Abl, Bcr-Abl, PDGFR, and c-Kit.1 It inhibits ligand-stimulated autophosphorylation of PDGFR and c-Kit (IC50s = ~0.3 and ~0.1 μM, respectively).1,2 Imatinib inhibits the proliferation of Bcr-Abl-dependent R10(–) cells (IC50s = ~35-40 nM) and HMC-1 cells expressing constitutively active c-Kit in a concentration-dependent manner.1,3 It prolongs survival in a mouse model of chronic myeloid leukemia when administered at a dose of 100 mg/kg twice per day.4 Imatinib (25 and 50 µM) also inhibits the replication of Middle East respiratory syndrome coronavirus (MERS-CoV) and severe acute respiratory syndrome CoV (SARS-CoV) in Vero E6 cells.5 It reduces viral titers in Vero cells infected with infectious bronchitis virus (IBV), a coronavirus, when used at a concentration of 10 µM via inhibition of IBV surface glycoprotein protein-induced syncytia formation and virus-cell fusion.6 Formulations containing imatinib have been used in the treatment of various cancers.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Heinrich, M.C., Griffith, D.J., Druker, B.J., et al. Inhibition of c-kit receptor tyrosine kinase activity by STI 571, a selective tyrosine kinase inhibitor. Blood 96(3), 925-932 (2000).

    2. Buchdunger, E., Zimmermann, J., Mett, H., et al. Inhibition of the Abl protein-tyrosine kinase in vitro and in vivo by a 2-phenylaminopyrimidine derivative. Cancer Res. 56(1), 100-104 (1996).

    3. Wolff, N.C., Veach, D.R., Tong, W.P., et al. PD166326, a novel tyrosine kinase inhibitor, has greater antileukemic activity than imatinib mesylate in a murine model of chronic myeloid leukemia. Blood 105(10), 3995-4003 (2005).

    4. Coleman, C.M., Sisk, J.M., Mingo, R.M., et al. Abelson kinase inhibitors are potent inhibitors of severe acute respiratory syndrome coronavirus and Middle East respiratory syndrome coronavirus fusion. J. Virol. 90(19), 8924-8933 (2016).

    5. Sisk, J.M., Frieman, M.B., and Machamer, C.E. Coronavirus S protein-induced fusion is blocked prior to hemifusion by Able kinase inhibitors. J. Gen. Virol. 99(5), 619-630 (2018).