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Ketotifen Fumarate

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Chemistry

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Also known as: 34580-14-8, Zaditen, Zaditor, Ketotifen hydrogen fumarate, Alaway, Hc 20,511 fumarate

Molecular Formula

C₂₃H₂₃NO₅S

Molecular Weight

425.5 g/mol

InChI Key

YNQQEYBLVYAWNX-WLHGVMLRSA-N

FDA UNII

HBD503WORO

A cycloheptathiophene blocker of histamine H1 receptors and release of inflammatory mediators. It has been proposed for the treatment of asthma, rhinitis, skin allergies, and anaphylaxis.

1 2D Structure

Ketotifen Fumarate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(E)-but-2-enedioic acid;2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,10,12-pentaen-8-one

2.1.2 InChI

InChI=1S/C19H19NOS.C4H4O4/c1-20-9-6-13(7-10-20)18-15-5-3-2-4-14(15)12-17(21)19-16(18)8-11-22-19;5-3(6)1-2-4(7)8/h2-5,8,11H,6-7,9-10,12H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

2.1.3 InChI Key

YNQQEYBLVYAWNX-WLHGVMLRSA-N

2.1.4 Canonical SMILES

CN1CCC(=C2C3=C(C(=O)CC4=CC=CC=C42)SC=C3)CC1.C(=CC(=O)O)C(=O)O

2.1.5 Isomeric SMILES

CN1CCC(=C2C3=C(C(=O)CC4=CC=CC=C42)SC=C3)CC1.C(=C/C(=O)O)\C(=O)O

2.2 Other Identifiers

2.2.1 UNII

HBD503WORO

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4,9-dihydro-4-(1-methyl-4-piperidylidene)-10h-benzo(4,5)-cyclohepta(1,2-b)thiophen-10-one

2. Fumarate, Ketotifen

3. Ketotifen

4. Ketotifene

5. Ketotiphen

6. Ketotiphene

7. Zaditen

2.3.2 Depositor-Supplied Synonyms

1. 34580-14-8

2. Zaditen

3. Zaditor

4. Ketotifen Hydrogen Fumarate

5. Alaway

6. Hc 20,511 Fumarate

7. Ketotifen Fumarate Salt

8. Ketotifen (fumarate)

9. Ketotifen Fumarate (zaditor)

10. Hc-20511 Fumarate

11. Ketotifen (as Fumarate)

12. Hbd503woro

13. Nsc-757415

14. Mls000069701

15. 4,9-dihydro-4-(1-methyl-4-piperidylidene)-10h-benzo(4,5)cyclohepta(1,2-b)thiophen-10-one Fumarate (1:1)

16. Smr000058462

17. 10h-benzo(4,5)cyclohepta(1,2-b)thiophen-10-one, 4,9-dihydro-4-(1-methyl-4-piperidinylidene)-, (e)-2-butenedioate (1:1)

18. 4-(1-methylpiperidin-4-ylidene)-4,9-dihydro-10h-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one Fumarate

19. 34580-14-8 (fumarate); 34580-13-7 (free Base)

20. (2e)-but-2-enedioic Acid; 2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),3(7),4,11,13-pentaen-8-one

21. Ketotifen Fumarate [usan:jan]

22. Sr-01000075951

23. Einecs 252-100-0

24. Unii-hbd503woro

25. Ketotifen Fumerate

26. Ketotifene Fumarato

27. (e)-but-2-enedioic Acid;10-(1-methylpiperidin-4-ylidene)-5h-benzo[1,2]cyclohepta[2,4-b]thiophen-4-one

28. Prestwick_743

29. Zaditen (tn)

30. Mfcd00079394

31. Fumarato De Cetotifeno

32. Ketotifenfumarate

33. Opera_id_1952

34. Schembl8809

35. Schembl8810

36. Chembl1633

37. Mls000758236

38. Mls001148200

39. Mls001401421

40. Spectrum1500668

41. Ketotifen Fumarate [mi]

42. Ketotifen Fumarate [jan]

43. Hms500f13

44. Hy-b0157a

45. Dtxsid30892970

46. Ketotifen Fumarate [usan]

47. Ketotifen Fumarate (jp17/usan)

48. Regid_for_cid_5282408

49. Hms1569k03

50. Hms1921a12

51. Hms2052o11

52. Hms2092g16

53. Hms2096k03

54. Hms2232k10

55. Hms2233c06

56. Hms3262m13

57. Hms3266d20

58. Hms3411j21

59. Hms3675j21

60. Hms3713k03

61. Hms3884g20

62. Ketotifen Fumarate [vandf]

63. Pharmakon1600-01500668

64. Ketotifen Fumarate [mart.]

65. Bcp23414

66. Ketotifen Fumarate [who-dd]

67. Tox21_500706

68. Ccg-40319

69. Nsc757415

70. S2024

71. Akos008901371

72. Ac-7589

73. Bcp9000812

74. Ccg-101110

75. Cs-1988

76. Ks-1206

77. Lp00706

78. Nc00360

79. Nsc 757415

80. Ketotifen Fumarate [orange Book]

81. Ncgc00094057-01

82. Ncgc00094057-02

83. Ncgc00094057-03

84. Ncgc00094057-04

85. Ncgc00094057-05

86. Ncgc00261391-01

87. 4,9-dihydro-4-(1-methylpiperidin-4-ylidene)-10h-benzo(4,5)cyclohepta(1,2-b)thiophene-10-one Fumarate

88. Smr000653460

89. Bcp0726000236

90. Eu-0100706

91. K0048

92. Sw196887-4

93. C74779

94. D01332

95. K 2628

96. 580k148

97. Ketotifen Hydrogen Fumarate [ep Monograph]

98. J-019659

99. Sr-01000075951-1

100. Sr-01000075951-3

101. Sr-01000075951-4

102. Sr-01000075951-6

103. Q27279844

104. Ketotifen Hydrogen Fumarate 1.0 Mg/ml In Methanol (as Free Base)

105. Ketotifen Hydrogen Fumarate, European Pharmacopoeia (ep) Reference Standard

106. Ketotifen For Peak Identification, European Pharmacopoeia (ep) Reference Standard

107. (e)-but-2-enedioic Acid,10-(1-methylpiperidin-4-ylidene)-5h-benzo[1,2]cyclohepta[3,4-b]thiophen-4-one

108. (e)-but-2-enedioic Acid;2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,10,12-pentaen-8-one

109. 4,9-dihydro-4-(1-methyl-4-piperidinylidene-10h-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one Fumarate

110. 4-(1-methylpiperidin-4-ylidene)-4h-benzo[4,5]cyclohepta[1,2-b]thiophen-10(9h)-one Fumarate

2.4 Create Date

2005-06-29

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₃NO₅S
Molecular Weight	425.5 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Exact Mass	425.12969401 g/mol
Monoisotopic Mass	425.12969401 g/mol
Topological Polar Surface Area	123 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	595
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 6
Drug Name	Alaway
Active Ingredient	Ketotifen fumarate
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	eq 0.025% base
Market Status	Over the Counter
Company	Bausch And Lomb

2 of 6
Drug Name	Ketotifen fumarate
PubMed Health	Ketotifen
Drug Classes	Mast Cell Stabilizer, Ophthalmologic Agent, Piperidine
Active Ingredient	Ketotifen fumarate
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	eq 0.025% base
Market Status	Over the Counter
Company	Alcon Pharms; Akorn

3 of 6
Drug Name	Zaditor
PubMed Health	Ketotifen
Drug Classes	Mast Cell Stabilizer, Ophthalmologic Agent, Piperidine
Active Ingredient	Ketotifen fumarate
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	eq 0.025% base
Market Status	Over the Counter
Company	Alcon Pharma

4 of 6
Drug Name	Alaway
Active Ingredient	Ketotifen fumarate
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	eq 0.025% base
Market Status	Over the Counter
Company	Bausch And Lomb

5 of 6
Drug Name	Ketotifen fumarate
PubMed Health	Ketotifen
Drug Classes	Mast Cell Stabilizer, Ophthalmologic Agent, Piperidine
Active Ingredient	Ketotifen fumarate
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	eq 0.025% base
Market Status	Over the Counter
Company	Alcon Pharms; Akorn

6 of 6
Drug Name	Zaditor
PubMed Health	Ketotifen
Drug Classes	Mast Cell Stabilizer, Ophthalmologic Agent, Piperidine
Active Ingredient	Ketotifen fumarate
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	eq 0.025% base
Market Status	Over the Counter
Company	Alcon Pharma

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antipruritics

Agents, usually topical, that relieve itching (pruritus). (See all compounds classified as Antipruritics.)

Anti-Allergic Agents

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)

Histamine H1 Antagonists

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Histamine-1 Receptor Inhibitor [EPC]; Histamine H1 Receptor Antagonists [MoA]

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