apremilast   

GtoPdb Ligand ID: 7372

Synonyms: CC-10004 | Otezla®
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
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
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
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2014), EMA (2015))
IUPAC Name
N-[2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-1,3-dioxoisoindol-4-yl]acetamide
International Nonproprietary Names
INN number INN
8872 apremilast
Synonyms
CC-10004 | Otezla®
Database Links
CAS Registry No. 608141-41-9 (source: SciFinder)
ChEMBL Ligand CHEMBL514800
DrugCentral Ligand 4829
GtoPdb PubChem SID 178103944
PubChem CID 11561674
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Wikipedia Apremilast