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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

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

PubMed

TitleDatePubMed
The discovery of setileuton, a potent and selective 5-lipoxygenase inhibitor.
2010 Jul 8
Novel cytochrome P450-mediated ring opening of the 1,3,4-oxadiazole in setileuton, a 5-lipoxygenase inhibitor.
2011 May
The efficacy and tolerability of MK-0633, a 5-lipoxygenase inhibitor, in chronic asthma.
2012 Jan
Patents

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
by admin
on Sat Dec 16 17:40:34 GMT 2023
Edited
by admin
on Sat Dec 16 17:40:34 GMT 2023
Record UNII
0U2750935P
Record Status Validated (UNII)
Record Version
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Name Type Language
SETILEUTON
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
SETILEUTON [USAN]
Common Name English
MK-0633
Code English
setileuton [INN]
Common Name English
4-(4-FLUOROPHENYL)-7-(((5-((1S)-1-HYDROXY-1-(TRIFLUOROMETHYL)PROPYL)-1,3,4-OXADIAZOL-2-YL)AMINIUM METHYL-2H-CHROMEN-2-ONE
Common Name English
2H-1-BENZOPYRAN-2-ONE, 4-(4-FLUOROPHENYL)-7-(((5-((1S)-1-HYDROXY-1-(TRIFLUOROMETHYL)PROPYL)-1,3,4-OXADIAZOL-2-YL)AMINO)METHYL)-
Systematic Name English
Setileuton [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1322
Created by admin on Sat Dec 16 17:40:34 GMT 2023 , Edited by admin on Sat Dec 16 17:40:34 GMT 2023
Code System Code Type Description
CAS
910656-27-8
Created by admin on Sat Dec 16 17:40:34 GMT 2023 , Edited by admin on Sat Dec 16 17:40:34 GMT 2023
PRIMARY
NCI_THESAURUS
C152347
Created by admin on Sat Dec 16 17:40:34 GMT 2023 , Edited by admin on Sat Dec 16 17:40:34 GMT 2023
PRIMARY
SMS_ID
300000034382
Created by admin on Sat Dec 16 17:40:34 GMT 2023 , Edited by admin on Sat Dec 16 17:40:34 GMT 2023
PRIMARY
FDA UNII
0U2750935P
Created by admin on Sat Dec 16 17:40:34 GMT 2023 , Edited by admin on Sat Dec 16 17:40:34 GMT 2023
PRIMARY
MESH
C568910
Created by admin on Sat Dec 16 17:40:34 GMT 2023 , Edited by admin on Sat Dec 16 17:40:34 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105653
Created by admin on Sat Dec 16 17:40:34 GMT 2023 , Edited by admin on Sat Dec 16 17:40:34 GMT 2023
PRIMARY
INN
9127
Created by admin on Sat Dec 16 17:40:34 GMT 2023 , Edited by admin on Sat Dec 16 17:40:34 GMT 2023
PRIMARY
PUBCHEM
11856170
Created by admin on Sat Dec 16 17:40:34 GMT 2023 , Edited by admin on Sat Dec 16 17:40:34 GMT 2023
PRIMARY
USAN
UU-70
Created by admin on Sat Dec 16 17:40:34 GMT 2023 , Edited by admin on Sat Dec 16 17:40:34 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY