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    Also known as: 111406-87-2, Zyflo, Leutrol, 1-(1-(benzo[b]thiophen-2-yl)ethyl)-1-hydroxyurea, Zileutonum, Abbott 64077
    Molecular Formula
    C11H12N2O2S
    Molecular Weight
    236.29  g/mol
    InChI Key
    MWLSOWXNZPKENC-UHFFFAOYSA-N
    FDA UNII
    V1L22WVE2S
    Zileuton
    Zileuton is a synthetic derivative of hydroxyurea with antiasthmatic properties. The leukotriene inhibitor zileuton blocks 5-lipoxygenase, which catalyzes the formation of leukotrienes from arachidonic acid; causes bronchodilation; decreases bronchial mucous secretion and edema; and may prevent or decrease the symptoms of asthma. (NCI04)
    Zileuton is a 5-Lipoxygenase Inhibitor. The mechanism of action of zileuton is as a 5-Lipoxygenase Inhibitor. The physiologic effect of zileuton is by means of Decreased Leukotriene Production.
    1 2D Structure

    Zileuton

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea
    2.1.2 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)
    2.1.3 InChI Key
    MWLSOWXNZPKENC-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C1=CC2=CC=CC=C2S1)N(C(=O)N)O
    2.2 Other Identifiers
    2.2.1 UNII
    V1L22WVE2S
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. A 64077

    2. A-64077

    3. Abbot 64077

    4. N-(1-benzo(b)thien-2-ylethyl)-n-hydroxyurea

    5. Zyflo

    2.3.2 Depositor-Supplied Synonyms

    1. 111406-87-2

    2. Zyflo

    3. Leutrol

    4. 1-(1-(benzo[b]thiophen-2-yl)ethyl)-1-hydroxyurea

    5. Zileutonum

    6. Abbott 64077

    7. Zileutonum [inn-latin]

    8. 1-[1-(1-benzothiophen-2-yl)ethyl]-1-hydroxyurea

    9. A-64077

    10. N-(1-benzo(b)thien-2-ylethyl)-n-hydroxyurea

    11. A 64077

    12. Zyflo (tn)

    13. Abbott-64077

    14. Urea, N-(1-benzo[b]thien-2-ylethyl)-n-hydroxy-

    15. Chembl93

    16. 1-[1-(1-benzothien-2-yl)ethyl]-1-hydroxyurea

    17. Nsc-730712

    18. Nsc-759277

    19. N-[1-(benzo[b]thiophen-2-yl)ethyl]-n-hydroxyurea

    20. V1l22wve2s

    21. (+-)-1-(1-benzo(b)thien-2-ylethyl)-1-hydroxyurea

    22. (+/-)-1-(1-benzo[b]thien-2-ylethyl)-1-hydroxyurea

    23. Zyflo Cr

    24. Chebi:10112

    25. N-(1-benzo[b]thien-2-ylethyl)-n-hydroxyurea

    26. (+-)-1-(1-benzo[b]thien-2-ylethyl)-1-hydroxyurea

    27. N-(1-benzo(b)thien-2-yl-ethyl)-n-hydroxyurea

    28. Ncgc00159453-02

    29. Dsstox_cid_3752

    30. Dsstox_rid_77185

    31. Dsstox_gsid_23752

    32. Urea, N-(1-benzo(b)thien-2-ylethyl)-n-hydroxy-

    33. Ziluton

    34. Zyflo Filmtab

    35. ( Inverted Exclamation Marka)-1(1-benzo[b]thien-2-ylethyl)-1-hydroxyure

    36. Smr000466377

    37. Cas-111406-87-2

    38. Zileuton (usp/inn)

    39. Sr-01000759349

    40. (+/-)-1-(1-benzo(b)thien-2-ylethyl)-1-hydroxyurea

    41. Unii-v1l22wve2s

    42. Cti-02

    43. Abt-077

    44. Zileuton [usan:usp:inn:ban]

    45. Zileuton- Bio-x

    46. Mfcd00866097

    47. Starbld0016861

    48. Zileuton [usan]

    49. Zileuton [inn]

    50. Zileuton [mi]

    51. Zileuton [vandf]

    52. Prestwick0_001090

    53. Zileuton [mart.]

    54. Zileuton [usp-rs]

    55. Zileuton [who-dd]

    56. Schembl4209

    57. Mls000759510

    58. Mls001424079

    59. Mls006011971

    60. Zileuton [orange Book]

    61. Gtpl5297

    62. Zileuton, >=98% (hplc)

    63. Dtxsid9023752

    64. Schembl18251470

    65. Zileuton [usp Monograph]

    66. Urea, N-(1-benzo(b)thien-2-ylethyl)-n-hydroxy-, (+-)-

    67. Hms2051m20

    68. Hms2089j12

    69. Hms2093h06

    70. Hms2235o04

    71. Hms3369i17

    72. Hms3393m20

    73. Hms3654j08

    74. Hms3714e07

    75. Hms3872f13

    76. Pharmakon1600-01505906

    77. Amy12540

    78. Bcp16199

    79. Tox21_111680

    80. Tox21_301148

    81. Bbl029070

    82. Bdbm50000541

    83. Nsc730712

    84. Nsc759277

    85. S1443

    86. Stl373010

    87. Akos000280127

    88. Akos016340558

    89. Tox21_111680_1

    90. Ccg-100901

    91. Ccg-213571

    92. Cs-1563

    93. Db00744

    94. Ks-1195

    95. Nc00151

    96. Nsc 730712

    97. Nsc 759277

    98. Sb19083

    99. Mrf-0000030

    100. Ncgc00159453-03

    101. Ncgc00159453-04

    102. Ncgc00159453-05

    103. Ncgc00159453-06

    104. Ncgc00255046-01

    105. Ac-13198

    106. Ac-31490

    107. Bz164573

    108. Hy-14164

    109. Sbi-0206869.p001

    110. Db-015071

    111. Bb 0261152

    112. Ft-0601582

    113. Ft-0675903

    114. Sw197531-3

    115. 1-(1-benzothiophen-2-ylethyl)-1-hydroxy-urea

    116. D00414

    117. N-(1-benzo[b]thien-2-ylethyl)-n-hydroxy-urea

    118. Ab00639921-06

    119. Ab00639921-08

    120. Ab00639921-09

    121. Ab00639921_10

    122. Ab00639921_11

    123. 406z872

    124. A802357

    125. Q202998

    126. J-002574

    127. J-525169

    128. Sr-01000759349-4

    129. Sr-01000759349-5

    130. Sr-01000759349-6

    131. Zileuton, Commercially Available As 600 Mg Tablets

    132. Brd-a56359832-001-04-6

    133. Z1551429725

    134. Zileuton, United States Pharmacopeia (usp) Reference Standard

    135. Urea, N-(1-benzo(b)thien-2-ylethyl)-n-hydroxy-, (+/-)-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 236.29 g/mol
    Molecular Formula C11H12N2O2S
    XLogP31.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count2
    Exact Mass236.06194880 g/mol
    Monoisotopic Mass236.06194880 g/mol
    Topological Polar Surface Area94.8 Ų
    Heavy Atom Count16
    Formal Charge0
    Complexity275
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameZyflo
    PubMed HealthZileuton (By mouth)
    Drug ClassesAnti-Inflammatory
    Drug LabelZileuton is an orally active inhibitor of 5-lipoxygenase, the enzyme that catalyzes the formation of leukotrienes from arachidonic acid. Zileuton has the chemical name ()-1-(1-Benzo[b]thien-2-ylethyl)-1-hydroxyurea and the following chemical struct...
    Active IngredientZileuton
    Dosage FormTablet
    RouteOral
    Strength600mg
    Market StatusPrescription
    CompanyChiesi Usa

    2 of 4  
    Drug NameZyflo cr
    PubMed HealthZileuton (By mouth)
    Drug ClassesAnti-Inflammatory
    Drug LabelZileuton is an orally active inhibitor of 5-lipoxygenase, the enzyme that catalyzes the formation of leukotrienes from arachidonic acid. Zileuton has the chemical name ()-1-(1-Benzo[b]thien-2-ylethyl)-1-hydroxyurea and the following chemical struct...
    Active IngredientZileuton
    Dosage FormTablet, extended release
    RouteOral
    Strength600mg
    Market StatusPrescription
    CompanyChiesi Usa

    3 of 4  
    Drug NameZyflo
    PubMed HealthZileuton (By mouth)
    Drug ClassesAnti-Inflammatory
    Drug LabelZileuton is an orally active inhibitor of 5-lipoxygenase, the enzyme that catalyzes the formation of leukotrienes from arachidonic acid. Zileuton has the chemical name ()-1-(1-Benzo[b]thien-2-ylethyl)-1-hydroxyurea and the following chemical struct...
    Active IngredientZileuton
    Dosage FormTablet
    RouteOral
    Strength600mg
    Market StatusPrescription
    CompanyChiesi Usa

    4 of 4  
    Drug NameZyflo cr
    PubMed HealthZileuton (By mouth)
    Drug ClassesAnti-Inflammatory
    Drug LabelZileuton is an orally active inhibitor of 5-lipoxygenase, the enzyme that catalyzes the formation of leukotrienes from arachidonic acid. Zileuton has the chemical name ()-1-(1-Benzo[b]thien-2-ylethyl)-1-hydroxyurea and the following chemical struct...
    Active IngredientZileuton
    Dosage FormTablet, extended release
    RouteOral
    Strength600mg
    Market StatusPrescription
    CompanyChiesi Usa

    4.2 Drug Indication

    For the prophylaxis and chronic treatment of asthma in adults and children 12 years of age and older.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 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.

    5.2 MeSH Pharmacological Classification

    Anti-Inflammatory Agents, Non-Steroidal

    Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

    Lipoxygenase Inhibitors

    Compounds that bind to and inhibit that enzymatic activity of LIPOXYGENASES. Included under this category are inhibitors that are specific for lipoxygenase subtypes and act to reduce the production of LEUKOTRIENES. (See all compounds classified as Lipoxygenase Inhibitors.)

    Leukotriene Antagonists

    A class of drugs designed to prevent leukotriene synthesis or activity by blocking binding at the receptor level. (See all compounds classified as Leukotriene Antagonists.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    ZILEUTON
    5.3.2 FDA UNII
    V1L22WVE2S
    5.3.3 Pharmacological Classes
    5-Lipoxygenase Inhibitors [MoA]; Decreased Leukotriene Production [PE]; 5-Lipoxygenase Inhibitor [EPC]
    5.4 Absorption, Distribution and Excretion

    Absorption

    Rapidly and almost completely absorbed. The absolute bioavailability is unknown.

    Route of 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.

    Volume of Distribution

    1.2 L/kg

    Clearance

    Apparent oral cl=7 mL/min/kg

    5.5 Metabolism/Metabolites

    Hepatic. Zileuton and its N-dehydroxylated metabolite are oxidatively metabolized by the cytochrome P450 isoenzymes 1A2, 2C9 and 3A4.

    Zileuton has known human metabolites that include Zileuton O-glucuronide.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.6 Biological Half-Life

    2.5 hours

    5.7 Mechanism of Action

    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. Due to the role of leukotrienes in the pathogenesis of asthma, modulation of leukotriene formation by interruption of 5-lipoxygenase activity may reduce airway symptoms, decrease bronchial smooth muscle tone, and improve asthma control.

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