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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2D Structure
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Physico-chemical Properties
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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
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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
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.
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