Synonym
Setileuton tosylate; Setileuton; MK-0633 Tosylate; MK0633 Tosylate; MK 0633 Tosylate
IUPAC/Chemical Name
4-(4-Fluorophenyl)-7-[[[5-[(1S)-1-hydroxy-1-(trifluoromethyl)propyl]-1,3,4-oxadiazol-2-yl]amino]methyl]-2H-1-benzopyran-2-one Tosylate
InChi Key
NDAZWYKPMVDGGE-BOXHHOBZSA-N
InChi Code
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
SMILES Code
O=C1C=C(C2=CC=C(F)C=C2)C3=CC=C(CNC4=NN=C([C@@](C(F)(F)F)(O)CC)O4)C=C3O1.OS(=O)(C5=CC=C(C)C=C5)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
The most common inflammatory disease of the airways is asthma among children affecting around 235 million people worldwide. 5-Lipoxygenase (5-LOX) is a crucial enzyme which helps in the conversion of arachidonic acid (AA) to leukotrienes (LTs), the lipid mediators. It is associated with several inflammation related disorders such as asthma, allergy, and atherosclerosis. Therefore, it is considered as a promising target against inflammation and asthma
5-LO inhibitors have potential therapeutic utility for the treatment of inflammatory disorders. Asthma, an inflammatory disorder of the lower airway, is characterized by variable and reversible bronchoconstriction, airway edema, mucus secretion, and airway remodeling, which leads to recurrent episodes of wheezing, breathlessness, chest tightness, and coughing
Preparing Stock Solutions
The following data is based on the
product
molecular weight
635.59
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Sinha S, Doble M, Manju SL. 5-Lipoxygenase as a drug target: A review on trends in inhibitors structural design, SAR and mechanism based approach. Bioorg Med Chem. 2019 Sep 1;27(17):3745-3759. doi: 10.1016/j.bmc.2019.06.040. Epub 2019 Jul 4. PMID: 31331653.
2: Maciolek CM, Ma B, Menzel K, Laliberte S, Bateman K, Krolikowski P, Gibson CR. Novel cytochrome P450-mediated ring opening of the 1,3,4-oxadiazole in setileuton, a 5-lipoxygenase inhibitor. Drug Metab Dispos. 2011 May;39(5):763-70. doi: 10.1124/dmd.110.037366. Epub 2011 Feb 16. PMID: 21325431.
3: Ducharme Y, Blouin M, Brideau C, Châteauneuf A, Gareau Y, Grimm EL, Juteau H, Laliberté S, MacKay B, Massé F, Ouellet M, Salem M, Styhler A, Friesen RW. The discovery of setileuton, a potent and selective 5-lipoxygenase inhibitor. ACS Med Chem Lett. 2010 Apr 13;1(4):170-4. doi: 10.1021/ml100029k. PMID: 24900191; PMCID: PMC4007958.
