Zileuton
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MedKoo CAT#: 318995

CAS#: 111406-87-2

Description: Zileuton is an orally active inhibitor of 5-lipoxygenase, and thus inhibits leukotrienes (LTB4, LTC4, LTD4, and LTE4) formation. Zileuton is used for the maintenance treatment of asthma. Zileuton was introduced in 1996.


Chemical Structure

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Zileuton
CAS# 111406-87-2

Theoretical Analysis

MedKoo Cat#: 318995
Name: Zileuton
CAS#: 111406-87-2
Chemical Formula: C11H12N2O2S
Exact Mass: 236.06195
Molecular Weight: 236.289
Elemental Analysis: C, 55.92; H, 5.12; N, 11.86; O, 13.54; S, 13.57

Size Price Shipping out time Quantity
10mg USD 150 2 Weeks
25mg USD 250 2 Weeks
50mg USD 450 2 Weeks
100mg USD 650 2 Weeks
200mg USD 950 2 Weeks
500mg USD 1450 2 Weeks
1g USD 2450 2 Weeks
2g USD 3850 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-02-28. Prices are subject to change without notice.

Zileuton, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).

Synonym: A-64077; A64077; A 64077; Zileuton; trade name ZYFLO; ZYFLO CR.

IUPAC/Chemical Name: 1-(1-(benzo[b]thiophen-2-yl)ethyl)-1-hydroxyurea

InChi Key: MWLSOWXNZPKENC-UHFFFAOYSA-N

InChi Code: InChI=1S/C11H12N2O2S/c1-7(13(15)11(12)14)10-6-8-4-2-3-5-9(8)16-10/h2-7,15H,1H3,(H2,12,14)

SMILES Code: O=C(N)N(C(C1=CC2=CC=CC=C2S1)C)O

Appearance:
Solid powder

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, not in water

Shelf Life:
>2 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

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 236.289 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.

Select a batch to recalculate based on the batch molecular weight:
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

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1: Kuvibidila S, Warrier RP, Haynes J, Baliga SB. Hydroxyurea and Zileuton Differentially Modulate Cell Proliferation and Interleukin-2 Secretion by Murine Spleen Cells: Possible Implication on the Immune Function and Risk of Pain Crisis in Patients with Sickle Cell Disease. Ochsner J. 2015 Fall;15(3):241-7. PubMed PMID: 26412995; PubMed Central PMCID: PMC4569155.

2: Silva BC, de Miranda AS, Rodrigues FG, Malheiros Silveira AL, de Souza Resende GH, Dutra Moraes MF, Pinheiro de Oliveira AC, Parreiras PM, da Silva Barcelos L, Teixeira MM, Machado FS, Teixeira AL, Rachid MA. The 5-lipoxygenase (5-LOX) Inhibitor Zileuton Reduces Inflammation and Infarct Size with Improvement in Neurological Outcome Following Cerebral Ischemia. Curr Neurovasc Res. 2015;12(4):398-403. PubMed PMID: 26265153.

3: Liu Y, Wang W, Li Y, Xiao Y, Cheng J, Jia J. The 5-Lipoxygenase Inhibitor Zileuton Confers Neuroprotection against Glutamate Oxidative Damage by Inhibiting Ferroptosis. Biol Pharm Bull. 2015;38(8):1234-9. doi: 10.1248/bpb.b15-00048. PubMed PMID: 26235588.

4: Fuijkschot J, Seyger MM, Bastiaans DE, Wevers RA, Roeleveld N, Willemsen MA. Zileuton for Pruritus in Sjögren-Larsson Syndrome: A Randomized Double-blind Placebo-controlled Crossover Trial. Acta Derm Venereol. 2015 Jun 30. doi: 10.2340/00015555-2195. [Epub ahead of print] PubMed PMID: 26123322.

5: Prakash K, Adiki SK, Kalakuntla RR. Development and validation of a liquid chromatography-mass spectrometry method for the determination of zileuton in human plasma. Sci Pharm. 2014 Mar 26;82(3):571-83. doi: 10.3797/scipharm.1402-19. eCollection 2014 Sep. PubMed PMID: 25853069; PubMed Central PMCID: PMC4339974.

6: Gounaris E, Heiferman MJ, Heiferman JR, Shrivastav M, Vitello D, Blatner NR, Knab LM, Phillips JD, Cheon EC, Grippo PJ, Khazaie K, Munshi HG, Bentrem DJ. Zileuton, 5-lipoxygenase inhibitor, acts as a chemopreventive agent in intestinal polyposis, by modulating polyp and systemic inflammation. PLoS One. 2015 Mar 6;10(3):e0121402. doi: 10.1371/journal.pone.0121402. eCollection 2015. PubMed PMID: 25747113; PubMed Central PMCID: PMC4351892.

7: Zhang XY, Chen L, Xu DM, Wang XR, Wang YF, Li CT, Wei EQ, Zhang LH. [Zileuton, a 5-lipoxygenase inhibitor, attenuates mouse microglial cell-mediated rotenone toxicity in PC12 cells]. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2014 May;43(3):273-80. Chinese. PubMed PMID: 24998649.

8: Di Meco A, Lauretti E, Vagnozzi AN, Praticò D. Zileuton restores memory impairments and reverses amyloid and tau pathology in aged Alzheimer's disease mice. Neurobiol Aging. 2014 Nov;35(11):2458-64. doi: 10.1016/j.neurobiolaging.2014.05.016. Epub 2014 May 27. PubMed PMID: 24973121; PubMed Central PMCID: PMC4171192.

9: Gonca E. The effects of zileuton and montelukast in reperfusion-induced arrhythmias in anesthetized rats. Curr Ther Res Clin Exp. 2013 Dec;75:27-32. doi: 10.1016/j.curtheres.2013.06.001. PubMed PMID: 24465039; PubMed Central PMCID: PMC3898183.

10: Meng Z, Cao R, Yang Z, Liu T, Wang Y, Wang X. Inhibitor of 5-lipoxygenase, zileuton, suppresses prostate cancer metastasis by upregulating E-cadherin and paxillin. Urology. 2013 Dec;82(6):1452.e7-14. doi: 10.1016/j.urology.2013.08.060. PubMed PMID: 24295266.

11: Pian P, Labovitz E, Hoffman K, Clavijo CF, Rzasa Lynn R, Galinkin JL, Vinks AA, Malik P, Christians U. Quantification of the 5-lipoxygenase inhibitor zileuton in human plasma using high performance liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Oct 15;937:79-83. doi: 10.1016/j.jchromb.2013.08.014. Epub 2013 Aug 28. PubMed PMID: 24029553.

12: Chen WJ, Liaw SF, Lin CC, Lin MW, Chang FT. Effects of zileuton on airway smooth muscle remodeling after repeated allergen challenge in brown Norway rats. Respiration. 2013;86(5):421-9. doi: 10.1159/000353427. Epub 2013 Sep 10. PubMed PMID: 24021192.

13: Chu J, Li JG, Praticò D. Zileuton improves memory deficits, amyloid and tau pathology in a mouse model of Alzheimer's disease with plaques and tangles. PLoS One. 2013 Aug 7;8(8):e70991. doi: 10.1371/journal.pone.0070991. eCollection 2013. PubMed PMID: 23951061; PubMed Central PMCID: PMC3737232.

14: Shi SS, Yang WZ, Tu XK, Wang CH, Chen CM, Chen Y. 5-Lipoxygenase inhibitor zileuton inhibits neuronal apoptosis following focal cerebral ischemia. Inflammation. 2013 Dec;36(6):1209-17. doi: 10.1007/s10753-013-9657-4. PubMed PMID: 23695166.

15: Mohebati A, Milne GL, Zhou XK, Duffield-Lillico AJ, Boyle JO, Knutson A, Bosworth BP, Kingsley PJ, Marnett LJ, Brown PH, Akpa EG, Szabo E, Dannenberg AJ. Effect of zileuton and celecoxib on urinary LTE4 and PGE-M levels in smokers. Cancer Prev Res (Phila). 2013 Jul;6(7):646-55. doi: 10.1158/1940-6207.CAPR-13-0083. Epub 2013 May 16. PubMed PMID: 23682075; PubMed Central PMCID: PMC3707304.

16: Atemnkeng VA, Pink M, Schmitz-Spanke S, Wu XJ, Dong LL, Zhao KH, May C, Laufer S, Langer B, Kaiser A. Deoxyhypusine hydroxylase from Plasmodium vivax, the neglected human malaria parasite: molecular cloning, expression and specific inhibition by the 5-LOX inhibitor zileuton. PLoS One. 2013;8(3):e58318. doi: 10.1371/journal.pone.0058318. Epub 2013 Mar 7. PubMed PMID: 23505486; PubMed Central PMCID: PMC3591309.

17: Isikdemir F, Kurcer Z, Dengiz GO, Sipahi EY, Banoglu ZN, Baba F, Acikgoz S, Kelek S. Effects of montelukast and zileuton on testicular torsion/detorsion injury in rats. Andrologia. 2014 Feb;46(1):59-64. doi: 10.1111/and.12042. Epub 2012 Nov 9. PubMed PMID: 23137139.

18: Kubavat AH, Khippal N, Tak S, Rijhwani P, Bhargava S, Patel T, Shah N, Kshatriya RR, Mittal R. A randomized, comparative, multicentric clinical trial to assess the efficacy and safety of zileuton extended-release tablets with montelukast sodium tablets in patients suffering from chronic persistent asthma. Am J Ther. 2013 Mar-Apr;20(2):154-62. doi: 10.1097/MJT.0b013e318254259b. PubMed PMID: 22926233.

19: Woodruff PG, Albert RK, Bailey WC, Casaburi R, Connett JE, Cooper JA Jr, Criner GJ, Curtis JL, Dransfield MT, Han MK, Harnden SM, Kim V, Marchetti N, Martinez FJ, McEvoy CE, Niewoehner DE, Reilly JJ, Rice K, Scanlon PD, Scharf SM, Sciurba FC, Washko GR, Lazarus SC; Copd Clinical Research Network. Randomized trial of zileuton for treatment of COPD exacerbations requiring hospitalization. COPD. 2011 Feb;8(1):21-9. doi: 10.3109/15412555.2010.540273. PubMed PMID: 21299475; PubMed Central PMCID: PMC3775706.

20: Rossi A, Pergola C, Koeberle A, Hoffmann M, Dehm F, Bramanti P, Cuzzocrea S, Werz O, Sautebin L. The 5-lipoxygenase inhibitor, zileuton, suppresses prostaglandin biosynthesis by inhibition of arachidonic acid release in macrophages. Br J Pharmacol. 2010 Oct;161(3):555-70. doi: 10.1111/j.1476-5381.2010.00930.x. PubMed PMID: 20880396; PubMed Central PMCID: PMC2990155.