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Chemistry

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Also known as: 54143-56-5, Flecainide (acetate), Tambocor, R-818, Flecainide monoacetate, Flecainide acetate salt
Molecular Formula
C19H24F6N2O5
Molecular Weight
474.4  g/mol
InChI Key
RKXNZRPQSOPPRN-UHFFFAOYSA-N
FDA UNII
M8U465Q1WQ

Flecainide
A potent anti-arrhythmia agent, effective in a wide range of ventricular and atrial ARRHYTHMIAS and TACHYCARDIAS.
1 2D Structure

Flecainide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
acetic acid;N-(piperidin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide
2.1.2 InChI
InChI=1S/C17H20F6N2O3.C2H4O2/c18-16(19,20)9-27-12-4-5-14(28-10-17(21,22)23)13(7-12)15(26)25-8-11-3-1-2-6-24-11;1-2(3)4/h4-5,7,11,24H,1-3,6,8-10H2,(H,25,26);1H3,(H,3,4)
2.1.3 InChI Key
RKXNZRPQSOPPRN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=O)O.C1CCNC(C1)CNC(=O)C2=C(C=CC(=C2)OCC(F)(F)F)OCC(F)(F)F
2.2 Other Identifiers
2.2.1 UNII
M8U465Q1WQ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Apocard

2. Flcane

3. Flecadura

4. Flecainid Isis

5. Flecainid-isis

6. Flecainide

7. Flecainide Monoacetate

8. Flecainide Monoacetate, (+-)-isomer

9. Flecainide Monoacetate, (r)-isomer

10. Flecainide Monoacetate, (s)-isomer

11. Flecainide, (r)-isomer

12. Flecainide, (s)-isomer

13. Flecainide, 5-ho-n-(6-oxo)-derivative

14. Flecainide, 5-ho-n-(6-oxo)-derivative, (+-)-isomer

15. Flecatab

16. R818

17. Tambocor

2.3.2 Depositor-Supplied Synonyms

1. 54143-56-5

2. Flecainide (acetate)

3. Tambocor

4. R-818

5. Flecainide Monoacetate

6. Flecainide Acetate Salt

7. R 818

8. 54143-56-5 (acetate)

9. N-(2-piperidylmethyl)-2,5-bis-(2,2,2-trifluoroethoxy)benzamide Acetate

10. N-(piperidin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide Monoacetate

11. Mls000069675

12. Chebi:5091

13. M8u465q1wq

14. Apocard

15. Benzamide, N-(2-piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)-, Monoacetate

16. Benzamide, N-(2-piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)-,monoacetate

17. N-(2-piperidylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide Monoacetate

18. Smr000058451

19. Acetic Acid;n-(piperidin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide

20. N-(piperidin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide Acetate

21. Sr-01000000172

22. Einecs 258-997-5

23. Mfcd00214290

24. Unii-m8u465q1wq

25. Flecainidacetat

26. Tambocor (tn)

27. Flecainide Acetate [usan:usp:jan]

28. N-(2-piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide Monoacetate

29. Dsstox_cid_626

30. Opera_id_1587

31. 2,5-bis-(2,2,2-trifluoroethoxy)-n-(2-piperidinylmethyl)benzamide Acetate

32. Cas-54143-56-5

33. Dsstox_rid_75700

34. Dsstox_gsid_20626

35. Mls001148177

36. Mls002222300

37. Schembl121583

38. Chembl1200822

39. Dtxsid8020626

40. Flecainide Acetate [jan]

41. Flecainide Acetate (jp17/usp)

42. Flecainide For System Suitability

43. Flecainide Acetate [usan]

44. Flecainide Acetate [vandf]

45. Hms1570c12

46. Hms2097c12

47. Hms2231e15

48. Hms3259f11

49. Hms3267n04

50. Hms3369m07

51. Hms3412d09

52. Hms3676d09

53. Hms3714c12

54. Flecainide Acetate [mart.]

55. 11a-hydroxyepoxyprogesterone

56. Bcp17825

57. Flecainide Acetate [usp-rs]

58. Flecainide Acetate [who-dd]

59. Tox21_200208

60. Akos015889993

61. N-(piperidin-2-ylmethyl)-2,5-bis[(2,2,2-trifluoroethyl)oxy]benzamide Acetate

62. Ccg-220735

63. Cs-1400

64. Nc00641

65. Sb19142

66. Flecainide Acetate [ep Impurity]

67. Flecainide Acetate [orange Book]

68. Flecainide Acetate [ep Monograph]

69. Flecainide Acetate [usp Impurity]

70. Ncgc00093934-01

71. Ncgc00093934-02

72. Ncgc00257762-01

73. As-11702

74. Flecainide Acetate [usp Monograph]

75. Hy-17429

76. Db-052497

77. Eu-0100546

78. Ft-0630667

79. En300-51344

80. D00638

81. E-0735

82. F 6777

83. 143f565

84. Sr-01000000172-2

85. Sr-01000000172-4

86. Sr-01000000172-5

87. Sr-01000000172-7

88. Q27089351

89. Flecainide Acetate, British Pharmacopoeia (bp) Reference Standard

90. Flecainide Acetate, European Pharmacopoeia (ep) Reference Standard

91. 2,5-bis(2,2,2-trifluoroethoxy)-n-(2-piperidylmethyl)benzamide Acetate

92. Flecainide Acetate, United States Pharmacopeia (usp) Reference Standard

93. 2-({[2,5-bis(2,2,2-trifluoroethoxy)benzoyl]amino}methyl)piperidinium Acetate

94. Flecainide For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 474.4 g/mol
Molecular Formula C19H24F6N2O5
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count12
Rotatable Bond Count7
Exact Mass474.15894084 g/mol
Monoisotopic Mass474.15894084 g/mol
Topological Polar Surface Area96.9 Ų
Heavy Atom Count32
Formal Charge0
Complexity531
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 2  
Drug NameFlecainide acetate
Drug LabelFlecainide acetate is an antiarrhythmic drug available in tablets of 50, 100, or 150 mg for oral administration. Flecainide acetate is benzamide, N-(2-piperidinylmethyl)-2,5-bis (2,2,2-trifluoroethoxy)-monoacetate. Its molecular formula is C17H20F6N2...
Active IngredientFlecainide acetate
Dosage FormTablet
RouteOral
Strength100mg; 50mg; 150mg
Market StatusPrescription
CompanyRanbaxy; Amneal Pharm; Roxane; Barr

2 of 2  
Drug NameFlecainide acetate
Drug LabelFlecainide acetate is an antiarrhythmic drug available in tablets of 50, 100, or 150 mg for oral administration. Flecainide acetate is benzamide, N-(2-piperidinylmethyl)-2,5-bis (2,2,2-trifluoroethoxy)-monoacetate. Its molecular formula is C17H20F6N2...
Active IngredientFlecainide acetate
Dosage FormTablet
RouteOral
Strength100mg; 50mg; 150mg
Market StatusPrescription
CompanyRanbaxy; Amneal Pharm; Roxane; Barr

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Arrhythmia Agents

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)


Voltage-Gated Sodium Channel Blockers

A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS. (See all compounds classified as Voltage-Gated Sodium Channel Blockers.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Antiarrhythmic [EPC]

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API Reference Price

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09-Mar-2021
15-Oct-2024
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DOSAGE - TABLET;ORAL - 100MG **Federal Regist...DOSAGE - TABLET;ORAL - 100MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 18830

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DOSAGE - TABLET;ORAL - 150MG **Federal Regist...DOSAGE - TABLET;ORAL - 150MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 18830

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DOSAGE - TABLET;ORAL - 50MG **Federal Registe...DOSAGE - TABLET;ORAL - 50MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 18830

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