Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H17F4N3O4.C7H8O3S |
| Molecular Weight | 635.583 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC=C(C=C1)S(O)(=O)=O.CC[C@](O)(C2=NN=C(NCC3=CC4=C(C=C3)C(=CC(=O)O4)C5=CC=C(F)C=C5)O2)C(F)(F)F
InChI
InChIKey=NDAZWYKPMVDGGE-BOXHHOBZSA-N
InChI=1S/C22H17F4N3O4.C7H8O3S/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;1-6-2-4-7(5-3-6)11(8,9)10/h3-10,31H,2,11H2,1H3,(H,27,29);2-5H,1H3,(H,8,9,10)/t21-;/m0./s1
| Molecular Formula | C7H8O3S |
| Molecular Weight | 172.202 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C22H17F4N3O4 |
| Molecular Weight | 463.3817 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| The efficacy and tolerability of MK-0633, a 5-lipoxygenase inhibitor, in chronic asthma. | 2012-01 |
|
| Novel cytochrome P450-mediated ring opening of the 1,3,4-oxadiazole in setileuton, a 5-lipoxygenase inhibitor. | 2011-05 |
|
| The discovery of setileuton, a potent and selective 5-lipoxygenase inhibitor. | 2010-07-08 |
Patents
Sample Use Guides
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
Curator's Comment: Setileuton [MK-0633] was evaluated for its potency to inhibit the oxidation of arachidonic acid by recombinant human 5-LO (H5-LO), and the production of LTB4 in calcium ionophore-stimulated HWB.
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).
| Substance Class |
Chemical
Created
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Edited
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S184B1D161
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PARENT -> SALT/SOLVATE |
