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    Citalopram Hydrobromide

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 59729-32-7, Citalopram hbr, Celexa, Cipramil, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile hydrobromide, Elopram
    Molecular Formula
    C20H22BrFN2O
    Molecular Weight
    405.3  g/mol
    InChI Key
    WIHMBLDNRMIGDW-UHFFFAOYSA-N
    FDA UNII
    I1E9D14F36
    A furancarbonitrile that is one of the SELECTIVE SEROTONIN REUPTAKE INHIBITORS used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from TARDIVE DYSKINESIA in preference to tricyclic antidepressants, which aggravate dyskinesia.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile;hydrobromide
    2.1.2 InChI
    InChI=1S/C20H21FN2O.BrH/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20;/h4-9,12H,3,10-11,14H2,1-2H3;1H
    2.1.3 InChI Key
    WIHMBLDNRMIGDW-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F.Br
    2.2 Other Identifiers
    2.2.1 UNII
    I1E9D14F36
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Celexa

    2. Citalopram

    3. Cytalopram

    4. Lu-10-171

    5. Lu10171

    6. Seropram

    2.3.2 Depositor-Supplied Synonyms

    1. 59729-32-7

    2. Citalopram Hbr

    3. Celexa

    4. Cipramil

    5. 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile Hydrobromide

    6. Elopram

    7. Seropram

    8. Bonitrile Hbr

    9. Nitalapram Hbr

    10. Lu 10-171-b

    11. Citalopram (hydrobromide)

    12. Citalopram, Hydrobromide Salt

    13. Lu 10-171 Hbr

    14. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile;hydrobromide

    15. Nsc-758684

    16. Citalopram (as Hydrobromide)

    17. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile Hydrobromide

    18. I1e9d14f36

    19. Cipram

    20. (s)-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile Hydrobromide

    21. Lu 10-171

    22. Lu-10-171-b

    23. Citalopram D4 Hbr

    24. 59729-32-7 (hbr)

    25. 1-(3-(dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile Monohydrobromide

    26. 5-isobenzofurancarbonitrile, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-, Monohydrobromide

    27. Prepram Hbr

    28. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Hydrobromide

    29. Smr000326936

    30. Citalopram Hydrobromide [usan]

    31. Lu-10-171

    32. Sr-01000003129

    33. 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile Monohydrobromide

    34. Einecs 261-890-6

    35. C20h21fn2o.hbr

    36. Apertia

    37. Prisdal

    38. Lupram

    39. Sepram

    40. Unii-i1e9d14f36

    41. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile Hydrobromide

    42. Citalopram Hydrobromide [usan:usp]

    43. Celexa (tn)

    44. Mfcd02101306

    45. Cpd000326936

    46. Schembl1118

    47. Mls000758293

    48. Mls000860078

    49. Mls001401376

    50. Mls002222294

    51. Citalopram Hydrobromide (usp)

    52. Citalopram Hydrobromide Solution

    53. Chembl1200781

    54. Dtxsid40872344

    55. Pharmakon1600-01504172

    56. Citalopram Hydrogen Bromide- Bio-x

    57. Hy-b1287

    58. Lu-10-171b

    59. Citalopram Hydrobromide [mi]

    60. Tox21_500258

    61. Nsc758684

    62. S4749

    63. Zd 211

    64. Zd-211

    65. Citalopram Hydrobromide [hsdb]

    66. Akos005145738

    67. Ab10921

    68. Ac-1595

    69. Bcp9000537

    70. Ccg-101022

    71. Ccg-213271

    72. Citalopram Hydrobromide [mart.]

    73. Citalopram Hydrobromide [vandf]

    74. Cs-4735

    75. Ks-1043

    76. Lp00258

    77. Nc00272

    78. Nsc 758684

    79. Citalopram Hydrobromide [usp-rs]

    80. Citalopram Hydrobromide [who-dd]

    81. Ncgc00093717-01

    82. Ncgc00093717-02

    83. Ncgc00093717-03

    84. Ncgc00260943-01

    85. Bc164316

    86. Citalopram Hydrobromide, >=98% (hplc)

    87. Citalopram Hydrobromide [orange Book]

    88. Eu-0100258

    89. Ft-0600173

    90. Citalopram Hydrobromide [ep Monograph]

    91. Citalopram Hydrobromide [usp Impurity]

    92. C 7861

    93. C75790

    94. Citalopram Hydrobromide [usp Monograph]

    95. D00822

    96. 729c327

    97. A832439

    98. Q-200865

    99. Sr-01000003129-2

    100. Sr-01000003129-4

    101. W-105304

    102. Citalopram Hydrobromide 100 Microg/ml In Acetonitrile

    103. Q27280253

    104. Sr-01000003129-10

    105. Z1550648760

    106. Citalopram Hydrobromide 0.1 Mg/ml In Methanol (as Free Base)

    107. Citalopram Hydrobromide 1.0 Mg/ml In Methanol (as Free Base)

    108. Citalopram Hydrobromide, European Pharmacopoeia (ep) Reference Standard

    109. Citalopram Hydrobromide, United States Pharmacopeia (usp) Reference Standard

    110. 1-(3-(dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile Monohbr

    111. Citalopram For System Suitability, European Pharmacopoeia (ep) Reference Standard

    112. Citalopram Hydrobromide, Pharmaceutical Secondary Standard; Certified Reference Material

    113. 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile Hydrobromide

    114. 1-(3-dimethylaminopropyl)-1-(4'-fluorophenyl)-1, 3-dihydroisobenzofuran-5-carbonitrile Hbr

    115. 1-(3-dimethylaminopropyl)-1-(4'-fluorophenyl)-1, 3-dihydroisobenzofuran-5-carbonitrile Hydrobromide

    116. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitril E Hydrobromide

    117. 5-isobenzofurancarbonitrile, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-, Monohbr

    118. 5-isobenzofurancarbonitrile, 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-, Hydrobromide (1:1)

    119. Citalopram Hydrobromide Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

    120. Citalopram Hydrobromide Solution, 100 Mug/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 405.3 g/mol
    Molecular Formula C20H22BrFN2O
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count5
    Exact Mass404.08995 g/mol
    Monoisotopic Mass404.08995 g/mol
    Topological Polar Surface Area36.3 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity466
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameCelexa
    Active IngredientCitalopram hydrobromide
    Dosage FormTablet
    RouteOral
    Strengtheq 40mg base; eq 20mg base; eq 10mg base
    Market StatusPrescription
    CompanyForest Labs

    2 of 4  
    Drug NameCitalopram hydrobromide
    PubMed HealthCitalopram (By mouth)
    Drug ClassesAntidepressant
    Active IngredientCitalopram hydrobromide
    Dosage FormTablet; Capsule; Solution
    Routeorally disintegrating; Oral
    Strengtheq 40mg base; eq 10mg base/5ml; eq 20mg base; eq 10mg base; 40mg
    Market StatusPrescription
    CompanyMylan Pharms; Glenmark Generics; Silarx; Amneal Pharms Ny; Teva Pharms; Epic Pharma; Apotex; Aurobindo; Aurobindo Pharma; Sun Pharm Inds; Torrent Pharms; Dr Reddys Labs; Pliva; Invagen Pharms; Cipla; Mylan; Roxane; Biovail Labs Intl

    3 of 4  
    Drug NameCelexa
    Active IngredientCitalopram hydrobromide
    Dosage FormTablet
    RouteOral
    Strengtheq 40mg base; eq 20mg base; eq 10mg base
    Market StatusPrescription
    CompanyForest Labs

    4 of 4  
    Drug NameCitalopram hydrobromide
    PubMed HealthCitalopram (By mouth)
    Drug ClassesAntidepressant
    Active IngredientCitalopram hydrobromide
    Dosage FormTablet; Capsule; Solution
    Routeorally disintegrating; Oral
    Strengtheq 40mg base; eq 10mg base/5ml; eq 20mg base; eq 10mg base; 40mg
    Market StatusPrescription
    CompanyMylan Pharms; Glenmark Generics; Silarx; Amneal Pharms Ny; Teva Pharms; Epic Pharma; Apotex; Aurobindo; Aurobindo Pharma; Sun Pharm Inds; Torrent Pharms; Dr Reddys Labs; Pliva; Invagen Pharms; Cipla; Mylan; Roxane; Biovail Labs Intl

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Selective Serotonin Reuptake Inhibitors

    Compounds that specifically inhibit the reuptake of serotonin in the brain. (See all compounds classified as Selective Serotonin Reuptake Inhibitors.)

    Antidepressive Agents, Second-Generation

    A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake. (See all compounds classified as Antidepressive Agents, Second-Generation.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Serotonin Uptake Inhibitors [MoA]; Serotonin Reuptake Inhibitor [EPC]