An antagonist of cIAP1, cIAP2, and XIAP
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Birinapant

Item No. 19699

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,2'S)-N,N'-[(6,6'-difluoro[2,2'-bi-1H-indole]-3,3'-diyl)bis[methylene[(2R,4S)-4-hydroxy-2,1-pyrrolidinediyl][(1S)-1-ethyl-2-oxo-2,1-ethanediyl]]]bis[2-(methylamino)]-propanamide
CAS Number
1260251-31-7
Synonyms
  • TL-32711
Molecular Formula
C42H56F2N8O6
Formula Weight
806.9
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mLDMSO: 30 mg/mLDMSO:PBS (pH 7.2) (1:2): 0.33 mg/mlEthanol: 30 mg/mL
λmax
232, 285, 298, 331, 346, 365 nm
SMILES
O=C(N1[C@H](CC2=C(C3=C(C[C@H]4N(C([C@@H](NC([C@H](C)NC)=O)CC)=O)C[C@@H](O)C4)C(C=CC(F)=C5)=C5N3)NC6=C2C=CC(F)=C6)C[C@H](O)C1)[C@@H](NC([C@H](C)NC)=O)CC
InChi Code
InChI=1S/C42H56F2N8O6/c1-7-33(49-39(55)21(3)45-5)41(57)51-19-27(53)15-25(51)17-31-29-11-9-23(43)13-35(29)47-37(31)38-32(30-12-10-24(44)14-36(30)48-38)18-26-16-28(54)20-52(26)42(58)34(8-2)50-40(56)22(4)46-6/h9-14,21-22,25-28,33-34,45-48,53-54H,7-8,15-
InChi Key
PKWRMUKBEYJEIX-DXXQBUJASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $63

    Add

    5 mg

    $213

    Add

    10 mg

    $363

    Add

    25 mg

    $678

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Birinapant is a bivalent mimetic of the Diablo homolog known as second mitochondria-derived activator of caspase (Smac). It is an antagonist of cellular inhibitor of apoptosis 1 (cIAP1, or BIRC2), cIAP2 (BIRC3), and XIAP (BIRC4), binding each at nanomolar concentrations.1 Birinapant causes rapid cIAP1 degradation, caspase activation, PARP cleavage, and NF-κB activation in breast cancer cells.1 It shows in vivo antitumor activity, inducing apoptosis in several types of cancer xenografts in mice.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Allensworth, J.L., Sauer, S.J., Lyerly, H.K., et al. Smac mimetic Birinapant induces apoptosis and enhances TRAIL potency in inflammatory breast cancer cells in an IAP-dependent and TNF-α-independent mechanism. Breast Cancer Res. Treat. 137(2), 359-371 (2013).

    2. Krepler, C., Chunduru, S.K., Halloran, M.B., et al. The novel SMAC mimetic birinapant exhibits potent activity against human melanoma cells. Clin. Cancer Res. 19(7), 1784-1794 (2013).

    3. Nguyen, Q.D., Lavdas, I., Gubbins, J., et al. Temporal and spatial evolution of therapy-induced tumor apoptosis detected by caspase-3-selective molecular imaging. Clin. Cancer Res. 19(14), 3914-3924 (2013).