apremilast   Click here for help

GtoPdb Ligand ID: 7372

Synonyms: CC-10004 | Otezla®
Approved drug PDB Ligand Immunopharmacology Ligand
apremilast is an approved drug (FDA (2014), EMA (2015))
Compound class: Synthetic organic
Comment: Apremilast is an oral small molecule phosphodiesterase 4 (PDE4) inhibitor [1-2] (additional comment in [4]). It is selective for PDE4 over other PDE isozymes, but non-selective over PDE4 isoforms [5].
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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

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View more information in the IUPHAR Pharmacology Education Project: apremilast

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 7
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 127.46
Molecular weight 460.13
XLogP 2
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 CCOc1cc(ccc1OC)C(N1C(=O)c2c(C1=O)c(ccc2)NC(=O)C)CS(=O)(=O)C
Isomeric SMILES CCOc1cc(ccc1OC)[C@H](N1C(=O)c2c(C1=O)c(ccc2)NC(=O)C)CS(=O)(=O)C
InChI InChI=1S/C22H24N2O7S/c1-5-31-19-11-14(9-10-18(19)30-3)17(12-32(4,28)29)24-21(26)15-7-6-8-16(23-13(2)25)20(15)22(24)27/h6-11,17H,5,12H2,1-4H3,(H,23,25)/t17-/m1/s1
InChI Key IMOZEMNVLZVGJZ-QGZVFWFLSA-N
No information available.
Summary of Clinical Use Click here for help
Apremilast is approved to treat psoriatic arthritis (PsA). This drug is also in clinical trial as a potential treatment for several other inflammatory conditions. View a list of these trials at ClinicalTrials.gov. In the US and EU, apremilast has been granted orphan desigantion for the treatment of Behçet disease, an auto-immune disease which damages blood vessels and causes sores on mucosal membranes and occular and vascular inflammation.
In September 2014, the US FDA granted approval for the treatment of patients with moderate to severe plaque psoriasis, making Otezla® the first and only PDE4 inhibitor available for this indication.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Apremilast inhibits PDE4 [1]. Inhibition of PDE4 leads to an increase of cAMP concentration and modulation of multiple intracellular signalling pathways. This results in significant reduction of inflammatory cytokine production in T-cells, but since PDE4 subtypes have been identified in some skin cells, the drug effects may have other mechanisms alleviating psoriaritic symptoms [4]. Click here to go to the phosphodiesterases page.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)