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2D Structure
Also known as: 219861-08-2, Lexapro, (s)-citalopram oxalate, Cipralex, Escitalopram (oxalate), (s)-(+)citalopram oxalate
Molecular Formula
C22H23FN2O5
Molecular Weight
414.4  g/mol
InChI Key
KTGRHKOEFSJQNS-BDQAORGHSA-N
FDA UNII
5U85DBW7LO

S-enantiomer of CITALOPRAM. Belongs to a class of drugs known as SELECTIVE SEROTONIN REUPTAKE INHIBITORS, used to treat depression and generalized anxiety disorder.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile;oxalic acid
2.1.2 InChI
InChI=1S/C20H21FN2O.C2H2O4/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;3-1(4)2(5)6/h4-9,12H,3,10-11,14H2,1-2H3;(H,3,4)(H,5,6)/t20-;/m0./s1
2.1.3 InChI Key
KTGRHKOEFSJQNS-BDQAORGHSA-N
2.1.4 Canonical SMILES
CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F.C(=O)(C(=O)O)O
2.1.5 Isomeric SMILES
CN(C)CCC[C@@]1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F.C(=O)(C(=O)O)O
2.2 Other Identifiers
2.2.1 UNII
5U85DBW7LO
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Escitalopram

2. Lexapro

2.3.2 Depositor-Supplied Synonyms

1. 219861-08-2

2. Lexapro

3. (s)-citalopram Oxalate

4. Cipralex

5. Escitalopram (oxalate)

6. (s)-(+)citalopram Oxalate

7. Lu 26-054-0

8. Escitalopram (as Oxalate)

9. Citalopram Oxalate, (s)-

10. Nsc-758934

11. 5u85dbw7lo

12. Lu-26-054-0

13. (s)-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile Oxalate

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

15. Lu-26-054-o

16. Ncgc00095903-01

17. Dsstox_cid_26003

18. Dsstox_rid_81282

19. S-(+)-1-(3-(dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile Oxalate

20. Dsstox_gsid_46003

21. S-(+)-5-isobenzofurancarbonitrile, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-, Oxalate

22. Cas-219861-08-2

23. Escitalopram Oxalate [usan]

24. Gaudium

25. Entact

26. (s)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile Oxalate

27. Lexapro (tn)

28. Escitalopram Oxalate Inn

29. Unii-5u85dbw7lo

30. Schembl35123

31. Mls001401408

32. Spectrum1505216

33. (+)-(s)-citalopram Oxalate

34. Mld-55

35. (s)-citalopram Oxalate- Bio-x

36. Chembl1200322

37. Dtxsid1046003

38. Escitalopram Oxalate (jan/usp)

39. Escitalopram Oxalate [mi]

40. C20h21fn2o.c2h2o4

41. Escitalopram Oxalate [usan:usp]

42. Escitalopram Oxalate [jan]

43. Hms2051d11

44. Hms2231m16

45. Hms3370i17

46. Hms3393d11

47. Hms3713d16

48. Pharmakon1600-01505216

49. Bcp05686

50. Escitalopram Oxalate [vandf]

51. Tox21_111535

52. Ccg-39559

53. Escitalopram Oxalate [mart.]

54. Hy-14258a

55. Mfcd06407826

56. Nsc758934

57. Escitalopram Oxalate [usp-rs]

58. Escitalopram Oxalate [who-dd]

59. Akos016340275

60. Tox21_111535_1

61. Ac-6770

62. Cs-2054

63. Ks-1263

64. Nc00194

65. Nsc 758934

66. Sb17454

67. Ncgc00178555-02

68. 5-isobenzofurancarbonitrile, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-, (1s)-, Ethanedioate (1:1)

69. Bc164423

70. Escitalopram Oxalate [orange Book]

71. Smr000469191

72. Escitalopram Oxalate [ep Monograph]

73. Escitalopram Oxalate [usp Monograph]

74. E0958

75. D02567

76. Escitalopram Oxalate, >=98% (hplc), Powder

77. 861e082

78. A852070

79. Sr-01000763053

80. Sr-01000763053-3

81. Q27262882

82. Escitalopram Oxalate, Europepharmacopoeia (ep) Reference Standard

83. Escitalopram Oxalate, United States Pharmacopeia (usp) Reference Standard

84. Escitalopram For System Suitability, Europepharmacopoeia (ep) Reference Standard

85. Escitalopram Oxalate, Pharmaceutical Secondary Standard; Certified Reference Material

86. (+)-(s)-1-[3-(dimethylamino)propyl] -1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancar Bonitrile Oxalate

87. (+)-(s)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile Oxalate

88. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran-carbonitrile Oxalate

89. 5-isobenzofurancarbonitrile,1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-, (1s)-,ethanedioate (1:1)

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 414.4 g/mol
Molecular Formula C22H23FN2O5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count6
Exact Mass414.15910000 g/mol
Monoisotopic Mass414.15910000 g/mol
Topological Polar Surface Area111 Ų
Heavy Atom Count30
Formal Charge0
Complexity537
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
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 NameEscitalopram oxalate
PubMed HealthEscitalopram (By mouth)
Drug ClassesAntianxiety, Antidepressant
Drug LabelEscitalopramoxalate USPis an orally administered selective serotonin reuptake inhibitor (SSRI). Escitalopram is the pure S-enantiomer (single isomer) of the racemic bicyclic phthalane derivative citalopram. Escitalopram oxalate is designated S-(+...
Active IngredientEscitalopram oxalate
Dosage FormTablet; Solution
Routeoral; Oral
Strength5mg; eq 5mg base; eq 5mg base/5ml; 10mg; eq 20mg base; eq 10mg base; 20mg
Market StatusTentative Approval; Prescription
CompanyWatson Labs; Amneal Pharms; Mylan Pharma; Teva Pharms; Macleods Pharms; Caraco; Jubilant Generics; Sti Pharma; Apotex; Accord Hlthcare; Hetero Labs Ltd Iii; Aurobindo Pharma; Teva Pharms Usa; Taro; Torrent Pharms; Lupin; Zydus Pharms Usa; Dr Reddys Labs;

2 of 4  
Drug NameLexapro
Drug LabelLexapro (escitalopram oxalate) is an orally administered selective serotonin reuptake inhibitor (SSRI). Escitalopram is the pure S-enantiomer (single isomer) of the racemic bicyclic phthalane derivative citalopram. Escitalopram oxalate is designate...
Active IngredientEscitalopram oxalate
Dosage FormTablet; Solution
Routeoral; Oral
Strengtheq 5mg base; eq 5mg base/5ml; eq 20mg base; eq 10mg base
Market StatusPrescription
CompanyForest Labs

3 of 4  
Drug NameEscitalopram oxalate
PubMed HealthEscitalopram (By mouth)
Drug ClassesAntianxiety, Antidepressant
Drug LabelEscitalopramoxalate USPis an orally administered selective serotonin reuptake inhibitor (SSRI). Escitalopram is the pure S-enantiomer (single isomer) of the racemic bicyclic phthalane derivative citalopram. Escitalopram oxalate is designated S-(+...
Active IngredientEscitalopram oxalate
Dosage FormTablet; Solution
Routeoral; Oral
Strength5mg; eq 5mg base; eq 5mg base/5ml; 10mg; eq 20mg base; eq 10mg base; 20mg
Market StatusTentative Approval; Prescription
CompanyWatson Labs; Amneal Pharms; Mylan Pharma; Teva Pharms; Macleods Pharms; Caraco; Jubilant Generics; Sti Pharma; Apotex; Accord Hlthcare; Hetero Labs Ltd Iii; Aurobindo Pharma; Teva Pharms Usa; Taro; Torrent Pharms; Lupin; Zydus Pharms Usa; Dr Reddys Labs;

4 of 4  
Drug NameLexapro
Drug LabelLexapro (escitalopram oxalate) is an orally administered selective serotonin reuptake inhibitor (SSRI). Escitalopram is the pure S-enantiomer (single isomer) of the racemic bicyclic phthalane derivative citalopram. Escitalopram oxalate is designate...
Active IngredientEscitalopram oxalate
Dosage FormTablet; Solution
Routeoral; Oral
Strengtheq 5mg base; eq 5mg base/5ml; eq 20mg base; eq 10mg base
Market StatusPrescription
CompanyForest Labs

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.)


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