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2D Structure
Also known as: 103177-37-3, Azlaire, Ono-1078, Pranlukast hydrate, Ono 1078, Sb 205312
Molecular Formula
C27H23N5O4
Molecular Weight
481.5  g/mol
InChI Key
NBQKINXMPLXUET-UHFFFAOYSA-N
FDA UNII
TB8Z891092

Pranlukast is a cysteinyl leukotriene receptor-1 antagonist. It antagonizes or reduces bronchospasm caused, principally in asthmatics, by an allergic reaction to accidentally or inadvertently encountered allergens.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-[4-oxo-2-(2H-tetrazol-5-yl)chromen-8-yl]-4-(4-phenylbutoxy)benzamide
2.1.2 InChI
InChI=1S/C27H23N5O4/c33-23-17-24(26-29-31-32-30-26)36-25-21(23)10-6-11-22(25)28-27(34)19-12-14-20(15-13-19)35-16-5-4-9-18-7-2-1-3-8-18/h1-3,6-8,10-15,17H,4-5,9,16H2,(H,28,34)(H,29,30,31,32)
2.1.3 InChI Key
NBQKINXMPLXUET-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)CCCCOC2=CC=C(C=C2)C(=O)NC3=CC=CC4=C3OC(=CC4=O)C5=NNN=N5
2.2 Other Identifiers
2.2.1 UNII
TB8Z891092
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 8-(4 (4-phenylbutoxy)benzoyl)amino-2-(tetrazol-5'-yl)-4-oxo-4h-1-benzopyran

2. Ono 1078

3. Ono-1078

4. Ono-rs 411

5. Ono-rs-411

6. Sb 205312

2.3.2 Depositor-Supplied Synonyms

1. 103177-37-3

2. Azlaire

3. Ono-1078

4. Pranlukast Hydrate

5. Ono 1078

6. Sb 205312

7. Ccn 00401

8. Rs 411

9. Pranlukast (inn)

10. N-[4-oxo-2-(2h-tetrazol-5-yl)chromen-8-yl]-4-(4-phenylbutoxy)benzamide

11. Onon

12. Ono-rs-411

13. 4-oxo-8-(4-(4-phenylbutoxy)benzoylamino)-2-(tetrazol-5-yl)-4h-1-benzopyran

14. Chembl21333

15. N-(4-oxo-2-(1h-tetrazol-5-yl)-4h-chromen-8-yl)-4-(4-phenylbutoxy)benzamide

16. Ccn-00401

17. Rs-411

18. Tb8z891092

19. Ncgc00181765-01

20. Sb-205312

21. Pranlukast [inn]

22. N-(4-oxo-2-(1h-tetrazol-5-yl)-4h-1-benzopyran-8-yl)-p-(4-phenylbutoxy)benzamide

23. N-(4-oxo-2-(2h-tetrazol-5-yl)-4h-chromen-8-yl)-4-(4-phenylbutoxy)benzamide

24. 8-[4(4-phenylbutoxy)benzoyl]amino-2-(5-tetrazolyl)-4-oxo-4h-1-benzopyran;8-[4(4-phenylbutoxy)benzoyl]amino-2-(5-tetrazolyl)-4-oxo-4h-1-benzopyran

25. N-[4-oxo-2-(1h-tetrazol-5-yl)-4h-1-benzopyran-8-yl]-p-(4-phenylbutoxy)benzamide;n-[4-oxo-2-(1h-tetrazol-5-yl)-4h-1-benzopyran-8-yl]-p-(4-phenylbutoxy)benzamide

26. Azlaire (tn)

27. Pranlukast [inn:ban]

28. Sr-05000001474

29. Unii-tb8z891092

30. N-[4-oxo-2-(1h-tetrazol-5-yl)-4h-chromen-8-yl]-4-(4-phenylbutoxy)benzamide

31. N-[4-oxo-2-(2h-tetrazol-5-yl)-1-benzopyran-8-yl]-4-(4-phenylbutoxy)benzamide

32. Pranlukast [mi]

33. Pranlukast [mart.]

34. Schembl3693

35. Dsstox_cid_23782

36. Dsstox_rid_80074

37. Pranlukast [who-dd]

38. Dsstox_gsid_43782

39. Mls006010078

40. Gtpl3634

41. Ono Rs-411

42. Dtxsid3043782

43. Schembl18058592

44. Chebi:94810

45. Hms2089h16

46. Hms3650a14

47. Hms3714e03

48. Bcp04577

49. Hy-b0290

50. Zinc1542146

51. Tox21_112952

52. Ac-696

53. Bdbm50023198

54. Mfcd00864631

55. Akos015967342

56. Ccg-220661

57. Db01411

58. Sb19080

59. N-[4-oxo-2-(1h-tetrazol-5-yl)-4h-1-benzopyran-8-yl]-4-(4-phenylbutoxy)benzamide

60. As-15105

61. Smr004701229

62. Cas-103177-37-3

63. Ft-0652673

64. P2115

65. C71133

66. D08408

67. Ab01275471-01

68. 177p373

69. L013134

70. Q7238392

71. Sr-05000001474-1

72. Sr-05000001474-2

73. Sr-05000001474-3

74. Brd-k97045029-001-01-9

75. Brd-k97045029-001-04-3

76. 8-[4-(4-phenylbutyloxy)benzoyl]amino-2-(tetrazol-5-yl)-4-oxo-4h-1-benzopyran

77. Benzamide, N-(4-oxo-2-(1h-tetrazol-5-yl)-4h-1-benzopyran-8-yl)-4-(4-phenylbutoxy)-

78. N-[4-oxo-2-(1h-tetrazol-5-yl)-4h-1-benzopyran-8-yl]-4(4-phenylbutoxy)benzamide

79. N-[4-oxo-2-(1h-tetrazol-5-yl)-4h-chromen-8-yl]-4-(4-phenyl-butoxy)-benzamide

80. Benzamide, N-(4-oxo-2-(2h-tetrazol-5-yl)-4h-1-benzopyran-8-yl)-4-(4-phenylbutoxy)-

81. Knt

82. N-[4-oxo-2-(1h-tetrazol-5-yl)-4h-chromen-8-yl]-4-(4-phenyl-butoxy)-benzamide (ono-rs-411)

83. N-[4-oxo-2-(1h-tetrazol-5-yl)-4h-chromen-8-yl]-4-(4-phenyl-butoxy)-benzamide(ono-rs-411)

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 481.5 g/mol
Molecular Formula C27H23N5O4
XLogP34.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count9
Exact Mass481.17500423 g/mol
Monoisotopic Mass481.17500423 g/mol
Topological Polar Surface Area119 Ų
Heavy Atom Count36
Formal Charge0
Complexity778
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 Indication

Used as an adjunct to the standard therapy of inhaled steroids with inhaled long- and/or short-acting beta-agonists.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Pranlukast is a cysteinyl leukotriene receptor-1 antagonist.


5.2 MeSH Pharmacological Classification

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.)


Anti-Asthmatic Agents

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


5.3 ATC Code

R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03D - Other systemic drugs for obstructive airway diseases

R03DC - Leukotriene receptor antagonists

R03DC02 - Pranlukast


5.4 Metabolism/Metabolites

Hepatic


5.5 Mechanism of Action

Pranlukast selectively antagonizes leukotriene D4 (LTD4) at the cysteinyl leukotriene receptor, CysLT1, in the human airway. Pranlukast inhibits the actions of LTD4 at the CysLT1 receptor, preventing airway edema, smooth muscle contraction, and enhanced secretion of thick, viscous mucus.