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    Ketotifen Fumarate

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    2D Structure
    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

    2D Structure

    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 Weight 425.5 g/mol
    Molecular Formula C23H23NO5S
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count2
    Exact Mass425.12969401 g/mol
    Monoisotopic Mass425.12969401 g/mol
    Topological Polar Surface Area123 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity595
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 6  
    Drug NameAlaway
    Active IngredientKetotifen fumarate
    Dosage FormSolution/drops
    RouteOphthalmic
    Strengtheq 0.025% base
    Market StatusOver the Counter
    CompanyBausch And Lomb

    2 of 6  
    Drug NameKetotifen fumarate
    PubMed HealthKetotifen
    Drug ClassesMast Cell Stabilizer, Ophthalmologic Agent, Piperidine
    Active IngredientKetotifen fumarate
    Dosage FormSolution/drops
    RouteOphthalmic
    Strengtheq 0.025% base
    Market StatusOver the Counter
    CompanyAlcon Pharms; Akorn

    3 of 6  
    Drug NameZaditor
    PubMed HealthKetotifen
    Drug ClassesMast Cell Stabilizer, Ophthalmologic Agent, Piperidine
    Active IngredientKetotifen fumarate
    Dosage FormSolution/drops
    RouteOphthalmic
    Strengtheq 0.025% base
    Market StatusOver the Counter
    CompanyAlcon Pharma

    4 of 6  
    Drug NameAlaway
    Active IngredientKetotifen fumarate
    Dosage FormSolution/drops
    RouteOphthalmic
    Strengtheq 0.025% base
    Market StatusOver the Counter
    CompanyBausch And Lomb

    5 of 6  
    Drug NameKetotifen fumarate
    PubMed HealthKetotifen
    Drug ClassesMast Cell Stabilizer, Ophthalmologic Agent, Piperidine
    Active IngredientKetotifen fumarate
    Dosage FormSolution/drops
    RouteOphthalmic
    Strengtheq 0.025% base
    Market StatusOver the Counter
    CompanyAlcon Pharms; Akorn

    6 of 6  
    Drug NameZaditor
    PubMed HealthKetotifen
    Drug ClassesMast Cell Stabilizer, Ophthalmologic Agent, Piperidine
    Active IngredientKetotifen fumarate
    Dosage FormSolution/drops
    RouteOphthalmic
    Strengtheq 0.025% base
    Market StatusOver the Counter
    CompanyAlcon 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]