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Citalopram Hydrobromide

Synopsis, 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

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 Formula	C₂₀H₂₂BrFN₂O
Molecular Weight	405.3 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	404.08995 g/mol
Monoisotopic Mass	404.08995 g/mol
Topological Polar Surface Area	36.3 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	466
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Celexa
Active Ingredient	Citalopram hydrobromide
Dosage Form	Tablet
Route	Oral
Strength	eq 40mg base; eq 20mg base; eq 10mg base
Market Status	Prescription
Company	Forest Labs

2 of 4
Drug Name	Citalopram hydrobromide
PubMed Health	Citalopram (By mouth)
Drug Classes	Antidepressant
Active Ingredient	Citalopram hydrobromide
Dosage Form	Tablet; Capsule; Solution
Route	orally disintegrating; Oral
Strength	eq 40mg base; eq 10mg base/5ml; eq 20mg base; eq 10mg base; 40mg
Market Status	Prescription
Company	Mylan 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 Name	Celexa
Active Ingredient	Citalopram hydrobromide
Dosage Form	Tablet
Route	Oral
Strength	eq 40mg base; eq 20mg base; eq 10mg base
Market Status	Prescription
Company	Forest Labs

4 of 4
Drug Name	Citalopram hydrobromide
PubMed Health	Citalopram (By mouth)
Drug Classes	Antidepressant
Active Ingredient	Citalopram hydrobromide
Dosage Form	Tablet; Capsule; Solution
Route	orally disintegrating; Oral
Strength	eq 40mg base; eq 10mg base/5ml; eq 20mg base; eq 10mg base; 40mg
Market Status	Prescription
Company	Mylan 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]