cilomilast   Click here for help

GtoPdb Ligand ID: 7407

Synonyms: SB-207499
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: There is some ambiguity in the literature and on other database as to the exact structure of Cilomilast. The structure shown here matches that of the INN document, but the compound is represented on PubChem without specified stereochemistry by CID 151170.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 79.55
Molecular weight 343.18
XLogP 3.09
No. Lipinski's rules broken 0
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Canonical SMILES N#CC1(CCC(CC1)C(=O)O)c1ccc(c(c1)OC1CCCC1)OC
Isomeric SMILES N#C[C@@]1(CC[C@@H](CC1)C(=O)O)c1ccc(c(c1)OC1CCCC1)OC
InChI InChI=1S/C20H25NO4/c1-24-17-7-6-15(12-18(17)25-16-4-2-3-5-16)20(13-21)10-8-14(9-11-20)19(22)23/h6-7,12,14,16H,2-5,8-11H2,1H3,(H,22,23)/t14-,20-
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Summary of Clinical Use Click here for help
Cilomilast is being investigated for the treatment of conditions such as chronic obstructive pulmonary disease (COPD), bronchopulmonary dysplasia and asthma. lists one completed trial for this compound (NCT00103922)
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Cilomilast is a selective phosphodiesterase-4 (PDE4) inhibitor IC50 120nM [2]. This action is believed to confer the compound's anti-inflammatory activity. In vitro studies have shown that cilomilast suppresses LPS-induced TNF-α formation in isolated human monocytes (pIC50 7.0) and produces a modest inhibition of fMLP-induced degranulation of human neutrophils (pIC50 7.1) [1].