Birinapant
Birinapant Basic information
- Product Name:
- Birinapant
- Synonyms:
-
- Birinapant
- Birinapant (TL32711)
- TL 32711
- Birinapant(TL32711)/TL-32711/TL32711/TL-32711
- (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
- Propanamide, 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)-, (2S,2'S)-
- (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 Birinapant TL 32711
- Birinapant (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:
- 1260251-31-7
- MF:
- C42H56F2N8O6
- MW:
- 806.94
- Product Categories:
-
- Inhibitors
- Inhibitor
- Mol File:
- 1260251-31-7.mol
Birinapant Chemical Properties
- Melting point:
- >245oC (dec.)
- Boiling point:
- 1090.5±65.0 °C(Predicted)
- Density
- 1.320±0.06(20.0000℃)
- storage temp.
- -20°C Freezer
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- pka
- 13.99±0.46(Predicted)
- form
- Solid
- color
- White to Off-White
Birinapant Usage And Synthesis
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. Birinapant causes rapid cIAP1 degradation, caspase activation, PARP cleavage, and NF-κB activation in breast cancer cells. It shows in vivo antitumor activity, inducing apoptosis in several types of cancer xenografts in mice.
Uses
Birinapant is a bivalent SMAC mimetic compound antagonist of TRAF2 associated cIAP1 and cIAP2.
Definition
ChEBI: Birinapant is a dipeptide.
Enzyme inhibitor
This rotationally symmetric SMAC mimetic antagonist and anticancer agent (FW = 806.94 g/mol; CAS 1260251-31-7) targets cellular Inhibitor of Apoptosis Protein (or cIAP1; Kd of <1 nM), arguably the most potent mammalian caspase inhibitor, showing single-agent efficacy due to its panIAP antagonism and causing rapid cIAP1 degradation, caspase activation, PARP cleavage, and NF-κB activation. When administered in combination with TNF-α, Birinapant is effective against a melanoma cell line with acquired resistance to BRAF inhibitors
target
XIAP
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