ChemicalBook > CAS DataBase List > Birinapant

Birinapant

Product Name
Birinapant
CAS No.
1260251-31-7
Chemical Name
Birinapant
Synonyms
CS-801;TL 32711;Birinapan;Birinapant;SMAC mimetic;TL-32711 ≥98%;Birinapant, >=98%;Birinapant (TL32711);TL 32711. Birinapant;Birinapant USP/EP/BP
CBNumber
CB12658183
Molecular Formula
C42H56F2N8O6
Formula Weight
806.94
MOL File
1260251-31-7.mol
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Birinapant Property

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
InChIKey
PKWRMUKBEYJEIX-AUTGSTJINA-N
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Safety

HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical
Product number
19699
Product name
Birinapant
Purity
≥95%
Packaging
1mg
Price
$57
Updated
2024/03/01
Cayman Chemical
Product number
19699
Product name
Birinapant
Purity
≥95%
Packaging
5mg
Price
$193
Updated
2024/03/01
Cayman Chemical
Product number
19699
Product name
Birinapant
Purity
≥95%
Packaging
10mg
Price
$330
Updated
2024/03/01
Cayman Chemical
Product number
19699
Product name
Birinapant
Purity
≥95%
Packaging
25mg
Price
$616
Updated
2024/03/01
TRC
Product number
B399730
Product name
Birinapant
Packaging
5mg
Price
$140
Updated
2021/12/16
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Birinapant Chemical Properties,Usage,Production

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

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

Birinapant Preparation Products And Raw materials

Raw materials

Preparation Products

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Birinapant Suppliers

China 135 India 2 United States 22 Global 159
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View Lastest Price from Birinapant manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
Birinapant 1260251-31-7
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-26

1260251-31-7, BirinapantRelated Search:

Everolimus LCL-161 ABT 737 MG-132 GDC-0152 PLX4032

  • 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
  • Birinapant, >=98%
  • (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
  • Birinapant, Free Base
  • Birinapan
  • TL-32711 ≥98%
  • (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
  • TL 32711. Birinapant
  • TL-32711; TL32711; TL 32711. BIRINAPANT
  • CS-801
  • Birinapant USP/EP/BP
  • (2S,2'S)-N,N'-((2S,2'S)-((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)
  • SMAC mimetic
  • Birinapant, 10 mM in DMSO
  • (2S)-N-((2R)-1-((4S)-2-((6,6'-difluoro-3'-(((2S,4S)-4-hydroxy-1-(2-((S)-2-(methylamino)propanamido)butanoyl)pyrrolidin-2-yl)methyl)-1H,1'H-[2,2'-biindol]-3-yl)methyl)-4-hydroxypyrrolidin-1-yl)-1-oxobutan-2-yl)-2-(methylamino)propanamide
  • 1260251-31-7
  • C42H56F2N8O6
  • Inhibitors
  • Inhibitor