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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H17F4N3O4
Molecular Weight 463.3817
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SETILEUTON

SMILES

CC[C@](O)(C1=NN=C(NCC2=CC=C3C(OC(=O)C=C3C4=CC=C(F)C=C4)=C2)O1)C(F)(F)F

InChI

InChIKey=MAOIDRRXRLYJNV-NRFANRHFSA-N
InChI=1S/C22H17F4N3O4/c1-2-21(31,22(24,25)26)19-28-29-20(33-19)27-11-12-3-8-15-16(10-18(30)32-17(15)9-12)13-4-6-14(23)7-5-13/h3-10,31H,2,11H2,1H3,(H,27,29)/t21-/m0/s1

HIDE SMILES / InChI

Description

Setileuton [MK-0633] is a selective inhibitor of the 5-lipoxygenase enzyme, which was under investigation for the treatment of asthma and atherosclerosis. Setileuton has been in phase II clinical trials by Merck Sharp & Dohme for the treatment of asthma, chronic obstructive pulmonary disease (COPD) and atherosclerosis. However, this research has been discontinued.

Originator

Approval Year

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
This was a randomized, double-blind trial of once-daily Setileuton [MK-0633], 10 mg, 50 mg, and 100 mg, and placebo in patients 18-70 years with a history of chronic asthma, and FEV(1) ≥45 and ≤85% predicted. MK-0633 100 mg was significantly more effective than placebo for the change from baseline in FEV(1) (0.20 L vs. 0.13 L; p = 0.004).
Route of Administration: Oral
In Vitro Use Guide
Setileuton [MK-0633] inhibited 5-LO activity with an IC50 of 3.9 nM in the H5-LO assay and production of LTB4 with IC50 of 52 nM in the HWB assay. This excellent 5-LO inhibitory profile is accompanied by a relatively low affinity for the hERG channel(Ki= 6.3 uM).