Birinapant

Category	Human immunodeficiency Virus (HIV)
CAS	1260251-31-7
Description	Birinapant, also known as TL32711, is a synthetic small molecule and peptido mimetic of second mitochondrial-derived activator of caspases (SMAC) and inhibitor of IAP (Inhibitor of Apoptosis Protein) family proteins, with potential antineoplastic activity. As a SMAC mimetic and IAP antagonist, TL32711 binds to and inhibits the activity of IAPs, such as X chromosome-linked IAP (XIAP) and cellular IAPs 1 and 2. Since IAPs shield cancer cells from the apoptosis process, this agent may restore and promote the induction of apoptosis through apoptotic signaling pathways in cancer cells. IAPs are overexpressed by many cancer cell types and suppress apoptosis by binding and inhibiting active caspases-3, -7 and -9 via their baculoviral lAP repeat (BIR) domains. Check for active clinical trials or closed clinical trials using this agent.

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Product Information

Synonyms	TL-32711; TL32711; TL 32711. Birinapant
IUPAC Name	(2S)-N-[(2S)-1-[(2R,4S)-2-[[6-fluoro-2-[6-fluoro-3-[[(2R,4S)-4-hydroxy-1-[(2S)-2-[[(2S)-2-(methylamino)propanoyl]amino]butanoyl]pyrrolidin-2-yl]methyl]-1H-indol-2-yl]-1H-indol-3-yl]methyl]-4-hydroxypyrrolidin-1-yl]-1-oxobutan-2-yl]-2-(methylamino)propanamide
Molecular Weight	806.957
Molecular Formula	C42H56F2N8O6
Canonical SMILES	CCC(C(=O)N1CC(CC1CC2=C(NC3=C2C=CC(=C3)F)C4=C(C5=C(N4)C=C(C=C5)F)CC6CC(CN6C(=O)C(CC)NC(=O)C(C)NC)O)O)NC(=O)C(C)NC
InChI	InChI=1S/C42H56F2N8O6/c1-7-33(49-39(55)21(3)45-5)41(57)51-19-27(53)15-25(51)17-31-29-11-9-23(43)13-35(29)47-37(31)38-32(30-12-10-24(44)14-36(30)48-38)18-26-16-28(54)20-52(26)42(58)34(8-2)50-40(56)22(4)46-6/h9-14,21-22,25-28,33-34,45-48,53-54H,7-8,15-20H2,1-6H3,(H,49,55)(H,50,56)/t21-,22-,25-,26-,27-,28-,33-,34-/m0/s1
InChIKey	PKWRMUKBEYJEIX-DXXQBUJASA-N
Boiling Point	1090.5±65.0 °C at 760 mmHg
Flash Point	613.3±34.3 °C
Purity	>99.50%
Density	1.3±0.1 g/cm3
Solubility	In Vitro: DMSO : 125 mg/mL(154.91 mM;Need ultrasonic) In Vivo: 1.Add each solvent one by one:10% DMSO >> 40%PEG300 >> 5%Tween-80 >> 45% saline Solubility: ≥ 2.08 mg/mL (2.58 mM); Clear solution 2.Add each solvent one by one:10% DMSO >> 90% (20%SBE-β-CDin saline) Solubility: 2.08 mg/mL (2.58 mM); Suspended solution; Need ultrasonic 3.Add each solvent one by one:10% DMSO >> 90%corn oil Solubility: ≥ 2.08 mg/mL (2.58 mM); Clear solution
Appearance	white solid powder
Storage	Powder: -20°C 3 years 4°C 2 years In solvent: -80°C 6 months -20°C 1 months
Complexity	1350
Exact Mass	806.42908786
Index Of Refraction	1.628
In Vitro	Birinapant (TL32711) (30-10000 nM; 24 hours) significantly decreases the viability of SUM190 cells in a dose-dependent manner. Birinapant (TL32711) (30-1000 nM; 4 hours) shows a significant decrease in cIAP1 levels and enhanced PARP cleavage, and induces Apoptosis. Birinapant (TL32711) binds with high affinity to the isolated BIR3 domains of cIAP1, cIAP2, and XIAP and the single BIR domain of ML-IAP and rapidly degrades TRAF2-bound cIAP1 and cIAP2 thereby inhibiting TNF-mediated NF-κB activation.
In Vivo	Birinapant (TL32711) (30 mg/kg; i.p.; every third day (*5)) shows antitumor efficacy and are devoid of overt toxicity in preclinical models.
PSA	174.10000
Target	IAP; Apoptosis; HIV
Vapor Pressure	0.0±0.3 mmHg at 25°C
XLogP3-AA	3.3