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
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
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 |
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The discovery of setileuton, a potent and selective 5-lipoxygenase inhibitor. | 2010 Jul 8 |
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Novel cytochrome P450-mediated ring opening of the 1,3,4-oxadiazole in setileuton, a 5-lipoxygenase inhibitor. | 2011 May |
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The efficacy and tolerability of MK-0633, a 5-lipoxygenase inhibitor, in chronic asthma. | 2012 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21945511
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24900191
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
by
admin
on
Edited
Sat Dec 16 17:40:34 GMT 2023
by
admin
on
Sat Dec 16 17:40:34 GMT 2023
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Record UNII |
0U2750935P
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Record Status |
Validated (UNII)
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Record Version |
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C1322
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910656-27-8
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C152347
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300000034382
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0U2750935P
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C568910
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CHEMBL2105653
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UU-70
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TARGET -> INHIBITOR |
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SALT/SOLVATE -> PARENT |
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