An internal standard for the quantification of bortezomib
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Unlabeled Version(s)
10008822Bortezomib
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Bortezomib-d15

Item No. 22367

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N,N',N''-((2S,2'S,2''S)-(((1R,1'R,1''R)-(1,3,5,2,4,6-trioxatriborinane-2,4,6-triyl)tris(3-methylbutane-1,1-diyl))tris(azanediyl))tris(1-oxo-3-(phenyl-d5)propane-1,2-diyl))tris(pyrazine-2-carboxamide)
Synonyms
  • LDP-341-d15
  • MG-341-d15
  • PS-341-d15
Molecular Formula
C57H54D15B3N12O9
Formula Weight
1113.8
Purity
≥99% deuterated forms (d1-d15)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: soluble
SMILES
CC(C)C[C@H](NC([C@H](CC1=C([2H])C([2H])=C([2H])C([2H])=C1[2H])NC(C2=CN=CC=N2)=O)=O)B3OB([C@H](CC(C)C)NC([C@H](CC4=C([2H])C([2H])=C([2H])C([2H])=C4[2H])NC(C5=NC=CN=C5)=O)=O)OB([C@H](CC(C)C)NC([C@H](CC6=C([2H])C([2H])=C([2H])C([2H])=C6[2H])NC(C7=CN=CC=N7)=O)=O)O3
InChi Code
InChI=1S/C57H69B3N12O9/c1-37(2)28-49(70-52(73)43(31-40-16-10-7-11-17-40)67-55(76)46-34-61-22-25-64-46)58-79-59(50(29-38(3)4)71-53(74)44(32-41-18-12-8-13-19-41)68-56(77)47-35-62-23-26-65-47)81-60(80-58)51(30-39(5)6)72-54(75)45(33-42-20-14-9-15-21-42)69-57(78)48-36-63-24-27-66-48/h7-27,34-39,43-45,49-51H,28-33H2,1-6H3,(H,67,76)(H,68,77)(H,69,78)(H,70,73)(H,71,74)(H,72,75)/t43-,44-,45-,49-,50-,51-/m0/s1/i7D,8D,9D,10D,11D,12D,13D,14D,15D,16D,17D,18D,19D,20D,21D
InChi Key
YVBHFXUJMLXLKP-AIXSHOBKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    1 mg

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    Product Description

    Bortezomib-d15 is intended for use as an internal stadard for the quantification of bortezomib (Item No. 10008822) by GC- or LC-MS. When stored as a lyophilized solid, bortezomib exists as in a trimeric boroxine form but exists as the free boronic acid in solution.1 Bortezomib is a dipeptide boronic acid derivative that reversibly inhibits the 20S proteasome (Ki = 0.6 nM).2 It binds the β5-subunit of the 20S proteasome and selectively inhibits chymotryptic activity.3,4,5 Bortezomib blocks the degradation of tumor-suppressing and proapoptotic proteins to induce cell cycle arrest and apoptosis in cancer cell lines.2,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Byrn, S.R., Tishmack, P.A., Milton, M.J., et al. Analysis of two commercially available bortezomib products: differences in assay of active agent and impurity profile. AAPS PharmSciTech 12(2), 461-467 (2011).

    2. Yamauchi, T., Keating, M.J., and Plunkett, W. UCN-01 (7-hydroxystaurosporine) inhibits DNA repair and increases cytotoxicity in normal lymphocytes and chronic lymphocytic leukemia lymphocytes. Mol. Cancer Ther. 1, 287-294 (2002).

    3. Lightcap, E.S., McCormack, T.A., Pien, C.S., et al. Proteasome inhibition measurements: Clinical application. Clin. Chem. 46(5), 673-683 (2000).

    4. Adams, J. Development of the proteasome inhibitor PS-341. The Oncologist 7, 9-16 (2002).

    5. Dou, Q.P., and Zonder, J.A. Overview of proteasome inhibitor-based anti-cancer therapies: Perspective on bortezomib and second generation proteasome inhibitors versus future generation inhibitors of ubiquitin-proteasome system. Curr. Cancer Drug Targets 14(6), 517-536 (2014).

    6. Richardson, P.G., Hideshima, T., and Anderson, K.C. Bortezomib (PS-341): A novel, first-in-class proteasome inhibitor for the treatment of multiple myeloma and other cancers. Cancer Control 10(5), 361-369 (2003).