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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2014), EMA (2015))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
8872 apremilast
Synonyms Click here for help
CC-10004 | Otezla®
Database Links Click here for help
CAS Registry No. 608141-41-9 (source: SciFinder)
ChEMBL Ligand CHEMBL514800
DrugCentral Ligand 4829
GtoPdb PubChem SID 178103944
PubChem CID 11561674
Search Google for chemical match using the InChIKey IMOZEMNVLZVGJZ-QGZVFWFLSA-N
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UniChem Compound Search for chemical match using the InChIKey IMOZEMNVLZVGJZ-QGZVFWFLSA-N
UniChem Connectivity Search for chemical match using the InChIKey IMOZEMNVLZVGJZ-QGZVFWFLSA-N
Wikipedia Apremilast