MK-0359   Click here for help

GtoPdb Ligand ID: 9852

Synonyms: L-454,560 [1] | L-454560 | MK0359
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: MK-0359 is a potent and selective, oral PDE4 inhibitor that has a competitive and reversible mode of interaction. MK-0359 is identified as L-454,560 [1] by citation in [2]. MK-0359 inhibits both the apo- (Mg2+ free) and holoenzyme ((Mg2+-bound) states of PDE4 [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 136.85
Molecular weight 587.15
XLogP 6.09
No. Lipinski's rules broken 1
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Canonical SMILES Cc1noc(n1)C(=Cc1cccc(c1)c1cc(cc2c1nccc2)C(S(=O)(=O)C)(C)C)c1ccc(cc1)S(=O)(=O)C
Isomeric SMILES Cc1noc(n1)/C(=C/c1cccc(c1)c1cc(cc2c1nccc2)C(S(=O)(=O)C)(C)C)/c1ccc(cc1)S(=O)(=O)C
InChI InChI=1S/C31H29N3O5S2/c1-20-33-30(39-34-20)28(22-11-13-26(14-12-22)40(4,35)36)17-21-8-6-9-23(16-21)27-19-25(31(2,3)41(5,37)38)18-24-10-7-15-32-29(24)27/h6-19H,1-5H3/b28-17+
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Summary of Clinical Use Click here for help
MK-0359 exhibited clinical efficacy in a Phase 2 study in asthma patients (NCT00482898), but caused gastrointestinal adverse effects [2]. It has completed Phase 2 studies in rheumatoid arthritis (NCT00482417) and chronic obstructive pulmonary disease (NCT00482235).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT00482235 A Study of MK0359 in Patients With Chronic Obstructive Pulmonary Disease (COPD)(0359-016) Phase 2 Interventional Merck Sharp & Dohme Corp.
NCT00482417 Efficacy and Safety Study of MK0359 in Patients With Arthritis (0359-017) Phase 2 Interventional Merck Sharp & Dohme Corp.
NCT00482898 A Study of MK0359 in Patients With Chronic Asthma (0359-013) Phase 2 Interventional Merck Sharp & Dohme Corp.