Birinapant
- TL32711
Axon 4150
CAS:
1260251-31-7
- Optical Purity: >99% e.e.
- Soluble in DMSO
- MF: C42H56F2N8O6
- MW: 806.94
Description
Birinapant is a cell permeable, orally bioavailable, synthetic bivalent small molecule peptido mimetics of second mitochondrial-derived activator of caspases (SMAC) and potent and selective inhibitor of IAP (Inhibitor of Apoptosis Protein) family proteins with Kd values of 45 nM and <1 nM for XIAP and cIAP1, respectively. SMAC mimetics Birinapant and LCL-161 (Axon 3902) are also negative regulators of HIV-1 transcription, promoting reversal of viral latency.
More Information
| Parent CAS No. | 1260251-31-7 |
|---|---|
| Chemical Name | (2S,2'S)-N,N'-((2S,2'S)-1,1'-((3S,3'S,5R,5'R)-5,5'-(6,6'-Difluoro-1H,1'H-2,2'-biindole-3,3'-diyl)bis(methylene)bis(3-hydroxypyrrolidine-5,1-diyl))bis(1-oxobutane-2,1-diyl))bis(2-(methylamino)propanamide) |
| extra_info | Sold in collaboration with Chemietek |
| SMILES | C1(=C(C[C@H]2N(C(=O)[C@H](CC)NC(=O)[C@H](C)NC)C[C@@H](O)C2)C2C=CC(F)=CC=2N1)C1NC2C=C(F)C=CC=2C=1C[C@@H]1C[C@H](O)CN1C(=O)[C@H](CC)NC([C@@H](NC)C)=O |&1:3,7,13,18,40,42,48,53,r| |
| MFCD | N.A. |
| InChi | N.A. |
| InChiKey | N.A. |
| CID | N.A. |
| Short Description | Bivalent Smac mimetic and potent antagonist for XIAP and cIAP1 inhibitor |
References
- CA Benetatos 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.
- C Krepler et al. The novel SMAC mimetic birinapant exhibits potent activity against human melanoma cells. Clin Cancer Res. 2013 Apr 1;19(7):1784-94.
- L Pache et al. BIRC2/cIAP1 Is a Negative Regulator of HIV-1 Transcription and Can Be Targeted by Smac Mimetics to Promote Reversal of Viral Latency. Cell Host Microbe. 2015 Sep 9;18(3):345-53.
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