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DSSTox_CID_3746

DSSTox_CID_3746

Synopsis, 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 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

DSSTox_CID_3746

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 Formula	C₃₁H₃₃N₃O₆S
Molecular Weight	575.7 g/mol
XLogP3	5.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	9
Exact Mass	575.20900695 g/mol
Monoisotopic Mass	575.20900695 g/mol
Topological Polar Surface Area	124 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	1010
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
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	Accolate
PubMed Health	Zafirlukast (By mouth)
Drug Classes	Anti-Inflammatory
Drug Label	Zafirlukast 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 Ingredient	Zafirlukast
Dosage Form	Tablet
Route	Oral
Strength	10mg; 20mg
Market Status	Prescription
Company	Astrazeneca

2 of 4
Drug Name	Zafirlukast
PubMed Health	Zafirlukast (By mouth)
Drug Classes	Anti-Inflammatory
Drug Label	Zafirlukast 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 Ingredient	Zafirlukast
Dosage Form	Tablet
Route	Oral
Strength	10mg; 20mg
Market Status	Prescription
Company	Dr Reddys Labs

3 of 4
Drug Name	Accolate
PubMed Health	Zafirlukast (By mouth)
Drug Classes	Anti-Inflammatory
Drug Label	Zafirlukast 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 Ingredient	Zafirlukast
Dosage Form	Tablet
Route	Oral
Strength	10mg; 20mg
Market Status	Prescription
Company	Astrazeneca

4 of 4
Drug Name	Zafirlukast
PubMed Health	Zafirlukast (By mouth)
Drug Classes	Anti-Inflammatory
Drug Label	Zafirlukast 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 Ingredient	Zafirlukast
Dosage Form	Tablet
Route	Oral
Strength	10mg; 20mg
Market Status	Prescription
Company	Dr 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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