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Chemistry

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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

Citalopram Hydrobromide
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

Citalopram Hydrobromide

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]

API Reference Price

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02-Jan-2021
29-Aug-2024
KGS
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