Birinapant

Birinapant (TL32711), a bivalent Smac mimetic, is a potent antagonist for XIAP and cIAP1 with Kds of 45 nM and less than 1 nM, respectively. Birinapant (TL32711) induces the autoubiquitylation and proteasomal degradation of cIAP1 and cIAP2 in intact cells, which results in formation of a RIPK1: caspase-8 complex, caspase-8 activation, and induction of tumor cell death. Birinapant (TL32711) targets TRAF2-associated cIAPs and abrogates TNF-induced NF-κB activation.

Product Specifications

CAS Number

[1260251-31-7]

Product Name Alternative

TL32711

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Apoptosis; HIV; IAP

Type

Reference compound

Related Pathways

Anti-infection; Apoptosis

Applications

Cancer-programmed cell death

Field of Research

Cancer

Assay Protocol

https://www.medchemexpress.com/Birinapant.html

Purity

99.70

Solubility

DMSO : 125 mg/mL (ultrasonic)

Smiles

FC1=CC2=C(C=C1)C(C[C@H]3N(C([C@@H](NC([C@@H](NC)C)=O)CC)=O)C[C@@H](O)C3)=C(C(N4)=C(C[C@H]5N(C([C@@H](NC([C@@H](NC)C)=O)CC)=O)C[C@@H](O)C5)C6=C4C=C(F)C=C6)N2

Molecular Formula

C42H56F2N8O6

Molecular Weight

806.94

Precautions

H302, H315, H319, H335

References & Citations

[1]Allensworth JL, 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. 2013 Jan;137 (2) :359-71.|[2]Krepler C, et al. The novel SMAC mimetic birinapant exhibits potent activity against human melanoma cells. Clin Cancer Res. 2013 Apr 1;19 (7) :1784-94.|[3]Nguyen QD, et al. Temporal and spatial evolution of therapy-induced tumor apoptosis detected by caspase-3-selective molecular imaging. Clin Cancer Res. 2013 Jul 15;19 (14) :3914-24.|[4]Benetatos CA, et al. Birinapant (TL32711), a bivalent SMAC mimetic, targets TRAF2-associated cIAPs, abrogates TNF-induced NF-κB activation, and is active in patient-derived xenograft models. Mol Cancer Ther. 2014 Apr;13 (4) :867-79.