panobinostat   Click here for help

GtoPdb Ligand ID: 7489

Synonyms: Farydak® | LBH-589 | LBH589
Approved drug PDB Ligand Antimalarial Ligand
panobinostat is an approved drug (EMA & FDA (2015))
Compound class: Synthetic organic
Comment: Panobinostat is a non-selective histone deacetylase (HDAC) inhibitor [3-4]. The compound also has antimalarial activity.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: panobinostat

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 4
Rotatable bonds 8
Topological polar surface area 77.15
Molecular weight 349.18
XLogP 2.98
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES ONC(=O)C=Cc1ccc(cc1)CNCCc1c(C)[nH]c2c1cccc2
Isomeric SMILES ONC(=O)/C=C/c1ccc(cc1)CNCCc1c(C)[nH]c2c1cccc2
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+
InChI Key FPOHNWQLNRZRFC-ZHACJKMWSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
Approved drug? Yes (EMA & FDA (2015))
IUPAC Name Click here for help
(E)-N-hydroxy-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enamide
International Nonproprietary Names Click here for help
INN number INN
8805 panobinostat
Synonyms Click here for help
Farydak® | LBH-589 | LBH589
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9679810
Reactome Reaction Reactome logo R-HSA-9679787
Other databases
CAS Registry No. 404950-80-7
ChEMBL Ligand CHEMBL483254
DrugCentral Ligand 4682
GtoPdb PubChem SID 187051792
PubChem CID 6918837
RCSB PDB Ligand LBH
Search Google for chemical match using the InChIKey FPOHNWQLNRZRFC-ZHACJKMWSA-N
Search Google for chemicals with the same backbone FPOHNWQLNRZRFC
Search PubMed clinical trials panobinostat
Search PubMed titles panobinostat
Search PubMed titles/abstracts panobinostat
UniChem Compound Search for chemical match using the InChIKey FPOHNWQLNRZRFC-ZHACJKMWSA-N
UniChem Connectivity Search for chemical match using the InChIKey FPOHNWQLNRZRFC-ZHACJKMWSA-N
Wikipedia Panobinostat