Panobinostat

Category	Human immunodeficiency Virus (HIV)
CAS	404950-80-7
Description	Panobinostat is a cinnamic hydroxamic acid analogue with potential antineoplastic activity. Panobinostat selectively inhibits histone deacetylase (HDAC), inducing hyperacetylation of core histone proteins, which may result in modulation of cell cycle protein expression, cell cycle arrest in the G2/M phase and apoptosis. In addition, this agent appears to modulate the expression of angiogenesis-related genes, such as hypoxia-inducible factor-1alpha (HIF-1a) and vascular endothelial growth factor (VEGF), thus impairing endothelial cell chemotaxis and invasion. HDAC is an enzyme that deacetylates chromatin histone proteins.

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Product Information

Synonyms	LBH589; LBH 589; LBH-589; NVP-LBH589; NVP-LBH 589; Panobinostat; trade name Farydak
IUPAC Name	(E)-N-hydroxy-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enamide
Molecular Weight	349.434
Molecular Formula	C21H23N3O2
Canonical SMILES	CC1=C(C2=CC=CC=C2N1)CCNCC3=CC=C(C=C3)C=CC(=O)NO
InChI	InChI=1S/C21H23N3O2/c1-15-18(19-4-2-3-5-20(19)23-15)12-13-22-14-17-8-6-16(7-9-17)10-11-21(25)24-26/h2-11,22-23,26H,12-14H2,1H3,(H,24,25)/b11-10+
InChIKey	FPOHNWQLNRZRFC-ZHACJKMWSA-N
Melting Point	114-117?C
Purity	>98%
Density	1.2±0.1 g/cm3
Solubility	In vitro: 10 mM in DMSO
Appearance	Light yellow to yellow Solid
Application	Antineoplastic Agents
Storage	Powder: -20°C: 3 years 4°C: 2 years In solvent: -80°C: 6 months -20°C: 1 month
Complexity	474
Exact Mass	349.17902698
Index Of Refraction	1.683
In Vitro	Panobinosta (LBH589) induces Apoptosis of both MOLT-4 and Reh cells in a time- and dose-dependent manner. Panobinosta treatment results in histone (H3K9 and H4K8) hyperacetylation and regulation of cell-cycle control genes in Reh cells. Panobinostat exhibites potent antiproliferative activity in human NSCLC cell lines with the IC50 ranging from 5 to 100 nM.
In Vivo	Panobinosta (10, 20 mg/kg, i.p.) significantly slows tumor growth derived from Meso and NSCLC cells in vivo models. Panobinosta markedly increases acetylation of histone H3 and H4 of H69 human SCLC cells harvest from SCID mice. Panobinostat (5, 10 and 20 mg/kg i.p.) demonstrates a clear benefit of decreased tumor burden, significantly improves TTE and reduces bone density loss in a disseminated multiple myeloma mouse model.
PSA	77.15000
Target	HDAC; Autophagy; HIV; Apoptosis
XLogP3-AA	3