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
1. Gudjonsson JE, Johnston A, Ellis CN. (2012)
Novel systemic drugs under investigation for the treatment of psoriasis.
J Am Acad Dermatol, 67 (1): 139-47. [PMID:22305044]
2. Man HW, Schafer P, Wong LM, Patterson RT, Corral LG, Raymon H, Blease K, Leisten J, Shirley MA, Tang Y et al.. (2009)
Discovery of (S)-N-[2-[1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl] acetamide (apremilast), a potent and orally active phosphodiesterase 4 and tumor necrosis factor-alpha inhibitor.
J Med Chem, 52 (6): 1522-4. [PMID:19256507]
3. Schafer P. (2012)
Apremilast mechanism of action and application to psoriasis and psoriatic arthritis.
Biochem Pharmacol, 83 (12): 1583-90. [PMID:22257911]
4. Schafer PH, Day RM. (2013)
Novel systemic drugs for psoriasis: mechanism of action for apremilast, a specific inhibitor of PDE4.
J Am Acad Dermatol, 68 (6): 1041-2. [PMID:23680197]
5. Schafer PH, Parton A, Capone L, Cedzik D, Brady H, Evans JF, Man HW, Muller GW, Stirling DI, Chopra R. (2014)
Apremilast is a selective PDE4 inhibitor with regulatory effects on innate immunity.
Cell Signal, 26 (9): 2016-29. [PMID:24882690]