| Identification | Back Directory | [Name]
Birinapant | [CAS]
1260251-31-7 | [Synonyms]
CS-801
TL 32711
Birinapan
Birinapant
TL-32711 ≥98%
Birinapant, >=98%
Birinapant (TL32711)
Birinapant USP/EP/BP
TL 32711. Birinapant
Birinapant, Free Base
TL-32711; TL32711; TL 32711. BIRINAPANT
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-PYRRO
(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]]]b
(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)-
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
(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 | [Molecular Formula]
C42H56F2N8O6 | [MDL Number]
MFCD25976869 | [MOL File]
1260251-31-7.mol | [Molecular Weight]
806.94 |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
13.99±0.46(Predicted) | [color ]
White to Off-White | [InChIKey]
PKWRMUKBEYJEIX-AUTGSTJINA-N |
| Hazard Information | Back Directory | [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 | [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 pan-
IAP 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 | [storage]
Store at -20°C | [References]
[1] JENNIFER L ALLENSWORTH. Smac mimetic Birinapant induces apoptosis and enhances TRAIL potency in inflammatory breast cancer cells in an IAP-dependent and TNF-α-independent mechanism.[J]. Breast Cancer Research and Treatment, 2013, 137 2: 359-371. DOI: 10.1007/s10549-012-2352-6
[2] CLEMENS KREPLER. The novel SMAC mimetic birinapant exhibits potent activity against human melanoma cells.[J]. Clinical Cancer Research, 2013, 19 7: 1784-1794. DOI: 10.1158/1078-0432.ccr-12-2518
[3] QUANG-Dé NGUYEN. Temporal and spatial evolution of therapy-induced tumor apoptosis detected by caspase-3-selective molecular imaging.[J]. Clinical Cancer Research, 2013, 19 14: 3914-3924. DOI: 10.1158/1078-0432.ccr-12-3814 |
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