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111406-87-2 molecular structure
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1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea

ChemBase ID: 624
Molecular Formular: C11H12N2O2S
Molecular Mass: 236.29018
Monoisotopic Mass: 236.06194863
SMILES and InChIs

SMILES:
s1c(C(N(O)C(=O)N)C)cc2c1cccc2
Canonical SMILES:
ON(C(c1cc2c(s1)cccc2)C)C(=O)N
InChI:
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)
InChIKey:
MWLSOWXNZPKENC-UHFFFAOYSA-N

Cite this record

CBID:624 http://www.chembase.cn/molecule-624.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea
IUPAC Traditional name
zileuton
1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea
Brand Name
Leutrol
Zyflo
Zyflo CR
Synonyms
Zileutonum [INN-Latin]
zileuton
Zileuton
1-(1-(benzo[b]thiophen-2-yl)ethyl)-1-hydroxyurea
(±)-N-hydroxy-N-(1-benzo[b]thien-2-ylethyl)urea
Zileuton
Zyflo CR
N-(1-Benzo[b]thien-2-yl-ethyl)-N-hydroxyurea
A-64077
Abbott 64077
Leutrol
ZYFLO
CAS Number
111406-87-2
MDL Number
MFCD00866097
PubChem SID
46506394
160964087
PubChem CID
60490

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 8.837783  H Acceptors
H Donor LogD (pH = 5.5) 2.0059743 
LogD (pH = 7.4) 1.9906728  Log P 2.006173 
Molar Refractivity 61.9595 cm3 Polarizability 24.979395 Å3
Polar Surface Area 66.56 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.01  LOG S -3.64 
Solubility (Water) 5.39e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
DMSO: ≥20 mg/mL at ~60 °C (warm up to 60 C for 5min) expand Show data source
Practically insoluble (0.5 mg/ml) expand Show data source
Apperance
White Solid expand Show data source
white to off-white powder expand Show data source
Melting Point
157-158°C expand Show data source
Hydrophobicity(logP)
0.9 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
Risk Statements
22-36 expand Show data source
Safety Statements
26 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H319 expand Show data source
GHS Precautionary statements
P305 + P351 + P338 expand Show data source
Storage Temperature
room temp expand Show data source
Target
5-lipoxygenase(5-LO) expand Show data source
Mechanism of Action
5-Lipoxygenase (5-LOX) inhibitor expand Show data source
inhibits leukotrienes (LTB4, LTC4, LTD4, and LTE4) formation expand Show data source
weak inhibitor of CYP 1A2 expand Show data source
Purity
≥98% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antiallergic expand Show data source
Antiinflammatory agent expand Show data source
Investigated for treatment of irritable bowel disease expand Show data source
Potential antiasthmatic agent expand Show data source
Empirical Formula (Hill Notation)
C11H12N2O2S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00744 external link
Item Information
Drug Groups approved; investigational
Description Leukotrienes are substances that induce numerous biological effects including augmentation of neutrophil and eosinophil migration, neutrophil and monocyte aggregation, leukocyte adhesion, increased capillary permeability, and smooth muscle contraction. These effects contribute to inflammation, edema, mucus secretion, and bronchoconstriction in the airways of asthmatic patients. Zileuton relieves such symptoms through its selective inhibition of 5-lipoxygenase, the enzyme that catalyzes the formation of leukotrienes from arachidonic acid. Specifically, it inhibits leukotriene LTB4, LTC4, LTD4, and LTE4 formation. Both the R(+) and S(-) enantiomers are pharmacologically active as 5-lipoxygenase inhibitors in in vitro systems.
Indication For the prophylaxis and chronic treatment of asthma in adults and children 12 years of age and older.
Pharmacology Zileuton is an asthma drug that differs chemically and pharmacologically from other antiasthmatic agents. It blocks leukotriene synthesis by inhibiting 5-lipoxygenase, an enzyme of the eicosanoid synthesis pathway. Current data indicates that asthma is a chronic inflammatory disorder of the airways involving the production and activity of several endogenous inflammatory mediators, including leukotrienes. Sulfido-peptide leukotrienes (LTC4, LTD4, LTE4, also known as the slow-releasing substances of anaphylaxis) and LTB4, a chemoattractant for neutrophils and eosinophils, are derived from the initial unstable product of arachidonic acid metabolism, leukotriene A4 (LTA4), and can be measured in a number of biological fluids including bronchoalveolar lavage fluid (BALF) from asthmatic patients. In humans, pretreatment with zileuton attenuated bronchoconstriction caused by cold air challenge in patients with asthma.
Toxicity The oral minimum lethal doses in mice and rats were 500-4000 and 300-1000 mg/kg in various preparations, respectively (providing greater than 3 and 9 times the systemic exposure [AUC] achieved at the maximum recommended human daily oral dose, respectively).
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Zileuton and its N-dehydroxylated metabolite are oxidatively metabolized by the cytochrome P450 isoenzymes 1A2, 2C9 and 3A4.
Absorption Rapidly and almost completely absorbed. The absolute bioavailability is unknown.
Half Life 2.5 hours
Protein Binding 93% bound to plasma proteins, primarily to albumin.
Elimination Elimination of zileuton is predominantly via metabolism with a mean terminal half-life of 2.5 hours.
The urinary excretion of the inactive N-dehydroxylated metabolite and unchanged zileuton each accounted for less than 0.5% of the dose.
Distribution * 1.2 L/kg
Clearance * Apparent oral cl=7 mL/min/kg
References
Berger W, De Chandt MT, Cairns CB: Zileuton: clinical implications of 5-Lipoxygenase inhibition in severe airway disease. Int J Clin Pract. 2007 Apr;61(4):663-76. [Pubmed]
Wenzel SE, Kamada AK: Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma. Ann Pharmacother. 1996 Jul-Aug;30(7-8):858-64. [Pubmed]
Malo PE, Bell RL, Shaughnessy TK, Summers JB, Brooks DW, Carter GW: The 5-lipoxygenase inhibitory activity of zileuton in in vitro and in vivo models of antigen-induced airway anaphylaxis. Pulm Pharmacol. 1994 Apr;7(2):73-9. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1443 external link
Research Area: Chronic obstructive pulmonary disease,Acute asthma
Biological Activity:
Zileuton (ZYFLO) 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. [1]
Sigma Aldrich - Z4277 external link
Biochem/physiol Actions
Zileuton is an anti-asthmatic, an inhibitor of 5-lipoxygenase; the initial enzyme in the biosynthesis of leukotrienes from arachidonic acid.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. Z4277.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - Z420000 external link
An inhibitor of 5-lipoxygenase, the initial enzyme in the biosynthesis of leukotrienes from Arachidonic Acid. Used as an antiasthmatic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Berger W, De Chandt MT, Cairns CB: Zileuton: clinical implications of 5-Lipoxygenase inhibition in severe airway disease. Int J Clin Pract. 2007 Apr;61(4):663-76. Pubmed
  • • Wenzel SE, Kamada AK: Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma. Ann Pharmacother. 1996 Jul-Aug;30(7-8):858-64. Pubmed
  • • Malo PE, Bell RL, Shaughnessy TK, Summers JB, Brooks DW, Carter GW: The 5-lipoxygenase inhibitory activity of zileuton in in vitro and in vivo models of antigen-induced airway anaphylaxis. Pulm Pharmacol. 1994 Apr;7(2):73-9. Pubmed
  • • http://en.wikipedia.org/wiki/Zileuton
  • • Carter, G.W., et al.: J. Pharmacol. Exp. Ther., 256, 929 (1991)
  • • Weinblatt, M.E., et al.: J. Rheumatol., 19, 1537 (1991)
  • • McGill, K and Busse, W.W.: Lancet, 348, 519 (1996)
  • • 1. Malo PE, Bell RL, Shaughnessy TK, Summers JB, Brooks DW, Carter GW. The 5-lipoxygenase inhibitory activity of zileuton in in vitro and in vivo models of antigen-induced airway anaphylaxis.
  • • Pulm Pharmacol. 1994 Apr;7(2):73-9
  • • 2. Lu P, Schrag ML, Slaughter DE, Raab CE, Shou M, Rodrigues AD. Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor.
  • • Drug Metab Dispos. 2003 Nov;31(11):1352-60.
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PATENTS

PATENTS

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