Zileuton
Zileuton (CAS 111406-87-2) is a pharmacological inhibitor targeting the enzyme 5-lipoxygenase (5-LOX). It inhibits conversion of arachidonic acid to leukotriene precursors, thereby attenuating formation of inflammatory leukotrienes (LTB4, LTC4, LTD4, LTE4). In rat leukocyte and basophilic leukemia assays, Zileuton exhibits inhibition with reported IC50 values of 0.3 µM and 0.5 µM, respectively. Research demonstrates that Zileuton induces COX-2 expression and PGE2 synthesis via PKCδ-dependent activation of ERK1/2 and Akt, suggesting cardioprotective potential against ischemia/reperfusion injury. Additionally, animal models indicate neuroprotective benefits by mitigating inflammatory responses after cerebral ischemia. Clinically, Zileuton is utilized for asthma management, targeting leukotriene-mediated airway inflammation.
Reference:
[1] Carter GW, Young PR, Albert DH, Bouska J, Dyer R, Bell RL, Summers JB, Brooks DW. 5-lipoxygenase inhibitory activity of zileuton. J Pharmacol Exp Ther. 1991;256(3):929-37.
[2] Hyun-Jeong Kwak, Kyoung-Mi Park, Hye-Eun Choi, Hyun-Joung Lim, Jin-Hee Park, Hyun-Young Park. The cardioprotective effects of zileuton, a 5-lipoxygenase inhibitor, are mediated by COX-2 via activation of PKCδ. Cellular Signalling 22 (2010) 80-87
[3] Tu XK, Yang WZ, Wang CH, Shi SS, Zhang YL, Chen CM, Yang YK, Jin CD, Wen S.Zileuton reduces inflammatory reaction and brain damage following permanent cerebral ischemia in rats. Inflammation. 2010;33(5):344-52.
| Physical Appearance | A solid |
| Storage | Store at -20°C |
| M.Wt | 236.29 |
| Cas No. | 111406-87-2 |
| Formula | C11H12N2O2S |
| Solubility | insoluble in H2O; ≥12.73 mg/mL in EtOH; ≥13.3 mg/mL in DMSO |
| Chemical Name | 1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea |
| SDF | Download SDF |
| Canonical SMILES | CC(c1cc(cccc2)c2[s]1)N(C(N)=O)O |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment [1]: | |
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Cell lines |
H9c2 cells |
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Preparation method |
The solubility of this compound in DMSO is > 13.3 mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below - 20 °C for several months. |
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Reacting condition |
0 ~ 100 μM; 0 ~ 24 hrs |
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Applications |
Zileuton induced COX-2 protein expression in time- and dose-dependent manners without changing the COX-1 protein level. After the treatment with 50 μM Zileuton for 5 hrs, the level of COX-2 protein peaked and sustained for up to 12 hrs. In addition, Zileuton treatment significantly inhibited the induction of cell death by H2O2. |
| Animal experiment [2]: | |
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Animal models |
A rat permanent MCAO model |
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Dosage form |
50 mg/kg; p.o. |
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Applications |
In a rat permanent MCAO model, Zileuton significantly reduced the neurological deficit and the cerebral infarction volume. HE staining showed that Zileuton reduced necrotic or ischemic injured neurons. In addition, Zileuton also markedly reduced MCAO-induced increases of MPO activity, MDA content, NF-κB p65 immuno-positive cells, iNOS mRNA and iNOS protein expression, as well as serum TNF-α and IL-1β levels. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: [1]. Hyun-Jeong Kwak, Kyoung-Mi Park, Hye-Eun Choi, Hyun-Joung Lim, Jin-Hee Park, Hyun-Young Park. The cardioprotective effects of zileuton, a 5-lipoxygenase inhibitor, are mediated by COX-2 via activation of PKCδ. Cellular Signalling 22 (2010) 80-87. [2]. Tu XK, Yang WZ, Wang CH, Shi SS, Zhang YL, Chen CM, Yang YK, Jin CD, Wen S.Zileuton reduces inflammatory reaction and brain damage following permanent cerebral ischemia in rats. Inflammation. 2010;33(5):344-52. |
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Quality Control & MSDS
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Chemical structure
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