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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 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 Formula	C₁₁H₁₂N₂O₂S
Molecular Weight	236.29 g/mol
XLogP3	1.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	236.06194880 g/mol
Monoisotopic Mass	236.06194880 g/mol
Topological Polar Surface Area	94.8 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	275
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Zyflo
PubMed Health	Zileuton (By mouth)
Drug Classes	Anti-Inflammatory
Drug Label	Zileuton 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 Ingredient	Zileuton
Dosage Form	Tablet
Route	Oral
Strength	600mg
Market Status	Prescription
Company	Chiesi Usa

2 of 4
Drug Name	Zyflo cr
PubMed Health	Zileuton (By mouth)
Drug Classes	Anti-Inflammatory
Drug Label	Zileuton 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 Ingredient	Zileuton
Dosage Form	Tablet, extended release
Route	Oral
Strength	600mg
Market Status	Prescription
Company	Chiesi Usa

3 of 4
Drug Name	Zyflo
PubMed Health	Zileuton (By mouth)
Drug Classes	Anti-Inflammatory
Drug Label	Zileuton 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 Ingredient	Zileuton
Dosage Form	Tablet
Route	Oral
Strength	600mg
Market Status	Prescription
Company	Chiesi Usa

4 of 4
Drug Name	Zyflo cr
PubMed Health	Zileuton (By mouth)
Drug Classes	Anti-Inflammatory
Drug Label	Zileuton 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 Ingredient	Zileuton
Dosage Form	Tablet, extended release
Route	Oral
Strength	600mg
Market Status	Prescription
Company	Chiesi 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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USDMF

01

Biophore India Pharmaceuticals Pvt L...

India

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Zileuton

GDUFA

DMF Review : Complete

Rev. Date : 2014-06-16

Pay. Date : 2014-06-05

DMF Number : 26446

Submission : 2012-09-26

Status : Active

Type : II

02

Emcure Pharmaceuticals Ltd

India

Antibody Engineering

Not Confirmed

03

Erregierre Spa

Italy

Antibody Engineering

Not Confirmed

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Msn Laboratories Private Ltd

India

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Not Confirmed

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Optimus Drugs Private Ltd

India

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06

Solara Active Pharma Sciences Ltd

India

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Tianish Laboratories Private Ltd

U.S.A

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9 API Suppliers

7 USDMF

4 EU WC

8 NDC API

7 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

1 Drugs in Development

INTERMEDIATES

2 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

12 FDF Dossiers

9 FDA Orange Book

3 Listed Dossiers

RELATED EXCIPIENT COMPANIES

1 Rochem International Inc

16 SPI Pharma

3 DKSH

5 Faran Shimi Pharmaceutical

5 Boai NKY Pharmaceuticals Ltd

11 Gangwal Healthcare

2 Nanjing Well Pharmaceutical

1 Pfanstiehl

1 ACG Worldwide

1 Aeon Procare

1 Alcedo Pharmachem

7 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

20 BASF

1 Clariant

10 Corel Pharma Chem

3 DFE Pharma

1 Finar

8 Gangwal Chemicals

5 Ideal Cures Pvt Ltd

4 Ingredion Pharma Solutions

17 Kerry

3 Kima Chemical

6 Lonza Capsugel

12 Microlex e.U

3 Novo Excipients

4 Pharmatrans-Sanaq

5 Pluviaendo

3 Prachin Chemical

1 Qianhao Chemical (Hebei) Co., Ltd

1 Qualicaps

19 Roquette

7 Seppic

5 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

1 Shijiazhuang Huaxu Pharmaceutical

10 Sigachi Industries

2 The Dow Chemical Company

1 Ulanqab Kema New Material

1 Valens Pharmachem

3 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

61 Fillers, Diluents & Binders

47 Coating Systems & Additives

39 Direct Compression

31 Disintegrants & Superdisintegrants

25 Controlled & Modified Release

23 Granulation

20 Thickeners and Stabilizers

17 Chewable & Orodispersible Aids

17 Taste Masking

16 Lubricants & Glidants

16 Co-Processed Excipients

11 Solubilizers

11 Film Formers & Plasticizers

8 Parenteral

6 Topical

5 Emulsifying Agents

5 Empty Capsules

5 API Stability Enhancers

4 Vegetarian Capsules