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    Chemistry

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    Also known as: 107753-78-6, Accolate, Olmoran, Ici-204219, Cyclopentyl (3-(2-methoxy-4-((o-tolylsulfonyl)carbamoyl)benzyl)-1-methyl-1h-indol-5-yl)carbamate, Accoleit
    Molecular Formula
    C31H33N3O6S
    Molecular Weight
    575.7  g/mol
    InChI Key
    YEEZWCHGZNKEEK-UHFFFAOYSA-N
    FDA UNII
    XZ629S5L50
    Zafirlukast
    Zafirlukast is a tolyl compound and leukotriene receptor antagonist (LTRA), with anti-asthmatic and potential capsular contracture-preventing activities. Upon administration, zafirlukast selectively and competitively binds to and blocks the cysteinyl leukotriene 1 receptor (CYSLTR1), thereby preventing the potent pro-inflammatory mediators leukotriene C4, D4 and E4 from binding. This prevents leukotriene-mediated actions, including enhanced migration of eosinophils and neutrophils, increased adhesion of leukocytes, increased monocyte and neutrophil aggregation, increased airway edema, inflammation, capillary permeability and bronchoconstriction. In addition, zafirlukast may decrease collagen deposition, fibrosis, and capsular thickness after implantation, thereby preventing scar tissue.
    Zafirlukast is a Leukotriene Receptor Antagonist. The mechanism of action of zafirlukast is as a Leukotriene Receptor Antagonist, and Cytochrome P450 2C9 Inhibitor.
    1 2D Structure

    Zafirlukast

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    cyclopentyl N-[3-[[2-methoxy-4-[(2-methylphenyl)sulfonylcarbamoyl]phenyl]methyl]-1-methylindol-5-yl]carbamate
    2.1.2 InChI
    InChI=1S/C31H33N3O6S/c1-20-8-4-7-11-29(20)41(37,38)33-30(35)22-13-12-21(28(17-22)39-3)16-23-19-34(2)27-15-14-24(18-26(23)27)32-31(36)40-25-9-5-6-10-25/h4,7-8,11-15,17-19,25H,5-6,9-10,16H2,1-3H3,(H,32,36)(H,33,35)
    2.1.3 InChI Key
    YEEZWCHGZNKEEK-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC=CC=C1S(=O)(=O)NC(=O)C2=CC(=C(C=C2)CC3=CN(C4=C3C=C(C=C4)NC(=O)OC5CCCC5)C)OC
    2.2 Other Identifiers
    2.2.1 UNII
    XZ629S5L50
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-(5-cyclopentyloxycarbonylamino-2-methylindol-3-yl-methyl)-3-methoxy-n-o-tolylsulfonylbenzamide

    2. Accolate

    3. Aeronix

    4. Ici 204,219

    5. Ici 204219

    6. Ici-204219

    7. Olmoran

    2.3.2 Depositor-Supplied Synonyms

    1. 107753-78-6

    2. Accolate

    3. Olmoran

    4. Ici-204219

    5. Cyclopentyl (3-(2-methoxy-4-((o-tolylsulfonyl)carbamoyl)benzyl)-1-methyl-1h-indol-5-yl)carbamate

    6. Accoleit

    7. Vanticon

    8. Ici 204219

    9. Ici 204,219

    10. Cyclopentyl 3-(2-methoxy-4-((o-tolylsulfonyl)carbamoyl)benzyl)-1-methylindole-5-carbamate

    11. Zafirlukast (accolate)

    12. Chembl603

    13. Aeronix

    14. Chebi:10100

    15. Xz629s5l50

    16. 4-(5-cyclopentyloxycarbonylamino-1-methyl-1h-indol-3-ylmethyl)-3-methoxy-n-o-tolylsulfonylbenzamide

    17. Ici-204,219

    18. Ncgc00164547-01

    19. Ncgc00164547-06

    20. Dsstox_cid_3746

    21. Dsstox_rid_77181

    22. Dsstox_gsid_23746

    23. Cyclopentyl 3-[2-methoxy-4-(2-methylphenylsulfonylcarbamoyl)benzyl]-1-methyl-1h-indol-5-ylcarbamate

    24. Cyclopentyl N-[3-[[2-methoxy-4-(o-tolylsulfonylcarbamoyl)phenyl]methyl]-1-methyl-indol-5-yl]carbamate

    25. Zafirst

    26. Respix

    27. C31h33n3o6s

    28. Accolate (tn)

    29. Cyclopentyl 3-{2-methoxy-4-[(o-tolylsulfonyl)carbamoyl]benzyl}-1-methyl-1h-indol-5-ylcarbamate

    30. Cyclopentyl N-{3-[(2-methoxy-4-{[(2-methylbenzene)sulfonyl]carbamoyl}phenyl)methyl]-1-methyl-1h-indol-5-yl}carbamate

    31. Smr000466316

    32. Cas-107753-78-6

    33. Sr-01000759386

    34. Zafirlucast

    35. Unii-xz629s5l50

    36. Zafirlukast (jan/usan/inn)

    37. Zafirlukast [usan:inn:ban]

    38. Zafirlukast- Bio-x

    39. Mfcd00864775

    40. Zafirlukast(accolate)

    41. Cpd000466316

    42. Zafirlukast [mi]

    43. Zafirlukast [inn]

    44. Zafirlukast [jan]

    45. Zafirlukast [usan]

    46. Zafirlukast [vandf]

    47. Schembl4175

    48. Zafirlukast [mart.]

    49. Zafirlukast [who-dd]

    50. Carbamic Acid, (3-((2-methoxy-4-((((2-methylphenyl)sulfonyl)amino)carbonyl)phenyl)methyl)-1-methyl-1h-indol-5-yl)-, Cyclopentyl Ester

    51. Cyclopentyl N-[3-[[2-methoxy-4-[(2-methylphenyl)sulfonylcarbamoyl]phenyl]methyl]-1-methylindol-5-yl]carbamate

    52. Mls000759421

    53. Mls001424064

    54. Mls006011771

    55. Bidd:gt0267

    56. Gtpl3322

    57. Dtxsid5023746

    58. Zafirlukast, >=98% (hplc)

    59. Zafirlukast [orange Book]

    60. Hms2051f12

    61. Hms2089j10

    62. Hms3393f12

    63. Hms3650a04

    64. Hms3655e13

    65. Hms3713j08

    66. Hms3745k03

    67. Zinc896717

    68. Bcp05226

    69. Tox21_112176

    70. Bdbm50009073

    71. S1633

    72. Stk646780

    73. Akos005577888

    74. Tox21_112176_1

    75. Ac-9018

    76. Ccg-101025

    77. Db00549

    78. Nc00275

    79. Sb19079

    80. Ncgc00164547-02

    81. Ncgc00164547-03

    82. Ncgc00164547-04

    83. Ncgc00164547-05

    84. As-12943

    85. Bz164562

    86. Cyclopentyl (1-methyl-3-{[2-(methyloxy)-4-({[(2-methylphenyl)sulfonyl]amino}carbonyl)phenyl]methyl}-1h-indol-5-yl)carbamate

    87. Cyclopentyl [3-(2-methoxy-4-{[(2-methylphenyl)sulfonyl]carbamoyl}benzyl)-1-methyl-1h-indol-5-yl]carbamate

    88. Hy-17492

    89. N-[3-[[2-methoxy-4-[[[(2-methylphenyl)sulfonyl]amino]carbonyl]phenyl]methyl]-1-methyl-1h-indol-5-yl]carbamic Acid Cyclopentyl Ester

    90. Ft-0601575

    91. Mls000759421-02

    92. Sw197655-3

    93. Z0029

    94. C07206

    95. D00411

    96. D92802

    97. Ab00639922-06

    98. Ab00639922-08

    99. Ab00639922_09

    100. 753z786

    101. A801752

    102. L001011

    103. Q928378

    104. Q-201940

    105. Sr-01000759386-4

    106. Sr-01000759386-5

    107. Sr-01000759386-9

    108. Brd-k71289571-001-06-4

    109. Z1551429730

    110. Carbamic Acid, (3-((2-methoxy-4-(((2-methylphenyl)sulfonyl)amino)carbonyl)phenyl)methyl)-1-methyl-1h-indol-5-yl)-, Cyclopentyl Ester

    111. Carbamic Acid, N-[3-[[2-methoxy-4-[[[(2-methylphenyl)sulfonyl]amino]carbonyl]phenyl]methyl]-1-methyl-1h-indol-5-yl]-, Cyclopentyl Ester

    112. Cyclopentyl (3-(2-methoxy-4-((o-tolylsulfonyl)-carbamoyl)benzyl)-1-methyl-1h-indol-5-yl)carbamate

    113. Cyclopentyl 3-(2-methoxy-4-(o-tolylsulfonylcarbamoyl)benzyl)-1-methyl-1h-indol-5-ylcarbamate

    114. Cyclopentyl N-[3-({2-methoxy-4-[(2-methylbenzenesulfonyl)carbamoyl]phenyl}methyl)-1-methyl-1h-indol-5-yl]carbamate

    115. Cyclopentyl N-[3-[[2-methoxy-4-[[[(2-methylphenyl)sulfonyl]amino]carbonyl]phenyl]methyl]-1-methyl-1h-indol-5-yl]carbamate

    116. Zlk

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 575.7 g/mol
    Molecular Formula C31H33N3O6S
    XLogP35.5
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count9
    Exact Mass575.20900695 g/mol
    Monoisotopic Mass575.20900695 g/mol
    Topological Polar Surface Area124 Ų
    Heavy Atom Count41
    Formal Charge0
    Complexity1010
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    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 NameAccolate
    PubMed HealthZafirlukast (By mouth)
    Drug ClassesAnti-Inflammatory
    Drug LabelZafirlukast is a synthetic, selective peptide leukotriene receptor antagonist (LTRA), with the chemical name 4-(5-cyclopentyloxy-carbonylamino-1-methyl-indol-3-ylmethyl)-3-methoxy-N-o-tolylsulfonylbenzamide. The molecular weight of zafirlukast is 575...
    Active IngredientZafirlukast
    Dosage FormTablet
    RouteOral
    Strength10mg; 20mg
    Market StatusPrescription
    CompanyAstrazeneca

    2 of 4  
    Drug NameZafirlukast
    PubMed HealthZafirlukast (By mouth)
    Drug ClassesAnti-Inflammatory
    Drug LabelZafirlukast is a synthetic, selective peptide leukotriene receptor antagonist (LTRA), with the chemical name 4-(5-cyclopentyloxy-carbonylamino-1-methyl-indol-3-ylmethyl)-3-methoxy-N-o-tolylsulfonylbenzamide. The molecular weight of zafirlukast is 575...
    Active IngredientZafirlukast
    Dosage FormTablet
    RouteOral
    Strength10mg; 20mg
    Market StatusPrescription
    CompanyDr Reddys Labs

    3 of 4  
    Drug NameAccolate
    PubMed HealthZafirlukast (By mouth)
    Drug ClassesAnti-Inflammatory
    Drug LabelZafirlukast is a synthetic, selective peptide leukotriene receptor antagonist (LTRA), with the chemical name 4-(5-cyclopentyloxy-carbonylamino-1-methyl-indol-3-ylmethyl)-3-methoxy-N-o-tolylsulfonylbenzamide. The molecular weight of zafirlukast is 575...
    Active IngredientZafirlukast
    Dosage FormTablet
    RouteOral
    Strength10mg; 20mg
    Market StatusPrescription
    CompanyAstrazeneca

    4 of 4  
    Drug NameZafirlukast
    PubMed HealthZafirlukast (By mouth)
    Drug ClassesAnti-Inflammatory
    Drug LabelZafirlukast is a synthetic, selective peptide leukotriene receptor antagonist (LTRA), with the chemical name 4-(5-cyclopentyloxy-carbonylamino-1-methyl-indol-3-ylmethyl)-3-methoxy-N-o-tolylsulfonylbenzamide. The molecular weight of zafirlukast is 575...
    Active IngredientZafirlukast
    Dosage FormTablet
    RouteOral
    Strength10mg; 20mg
    Market StatusPrescription
    CompanyDr Reddys Labs

    4.2 Drug Indication

    For the prophylaxis and chronic treatment of asthma.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Zafirlukast is a synthetic, selective peptide leukotriene receptor antagonist (LTRA) indicated for the prophylaxis and chronic treatment of asthma. Patients with asthma were found in one study to be 25-100 times more sensitive to the bronchoconstricting activity of inhaled LTD4 than nonasthmatic subjects. In vitro studies demonstrated that zafirlukast antagonized the contractile activity of three leukotrienes (LTC4, LTD4 and LTE4) in conducting airway smooth muscle from laboratory animals and humans. Zafirlukast prevented intradermal LTD4-induced increases in cutaneous vascular permeability and inhibited inhaled LTD4-induced influx of eosinophils into animal lungs.

    5.2 MeSH Pharmacological Classification

    Anti-Asthmatic Agents

    Drugs that are used to treat asthma. (See all compounds classified as Anti-Asthmatic Agents.)

    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
    ZAFIRLUKAST
    5.3.2 FDA UNII
    XZ629S5L50
    5.3.3 Pharmacological Classes
    Leukotriene Receptor Antagonist [EPC]; Leukotriene Receptor Antagonists [MoA]; Cytochrome P450 2C9 Inhibitors [MoA]
    5.4 ATC Code

    R - Respiratory system

    R03 - Drugs for obstructive airway diseases

    R03D - Other systemic drugs for obstructive airway diseases

    R03DC - Leukotriene receptor antagonists

    R03DC01 - Zafirlukast

    5.5 Absorption, Distribution and Excretion

    Absorption

    Rapidly absorbed following oral administration, reduced following a high-fat or high-protein meal.

    Route of Elimination

    The most common metabolic products are hydroxylated metabolites which are excreted in the feces.

    Volume of Distribution

    70 L

    Clearance

    apparent oral CL=20 L/h

    11.4 L/h [7-11 yrs]

    9.2 L/h [5-6 yrs]

    5.6 Metabolism/Metabolites

    Hepatic

    Zafirlukast has known human metabolites that include 3-hydroxycyclopentyl N-[3-({2-methoxy-4-[(2-methylbenzenesulfonyl)carbamoyl]phenyl}methyl)-1-methylindol-5-yl]carbamate and cyclopentyl N-[1-(hydroxymethyl)-3-({2-methoxy-4-[(2-methylbenzenesulfonyl)carbamoyl]phenyl}methyl)indol-5-yl]carbamate.

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

    5.7 Biological Half-Life

    10 hours

    5.8 Mechanism of Action

    Zafirlukast is a selective and competitive receptor antagonist of leukotriene D4 and E4 (LTD4 and LTE4), components of slow-reacting substance of anaphylaxis (SRSA). Cysteinyl leukotriene production and receptor occupation have been correlated with the pathophysiology of asthma, including airway edema, smooth muscle constriction, and altered cellular activity associated with the inflammatory process, which contribute to the signs and symptoms of asthma.

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    03-Jun-2024
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    DOSAGE - TABLET;ORAL - 10MG

    USFDA APPLICATION NUMBER - 20547

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