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Propafenone Hydrochloride

Synopsis, Chemistry

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TABLET;ORAL - 150MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, TABLET;ORAL - 225MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, TABLET;ORAL - 300MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, CAPSULE, EXTENDED RELEASE;ORAL - 225MG, CAPSULE, EXTENDED RELEASE;ORAL - 325MG, CAPSULE, EXTENDED RELEASE;ORAL - 425MG

TABLET;ORAL - 150MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
TABLET;ORAL - 225MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
TABLET;ORAL - 300MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
CAPSULE, EXTENDED RELEASE;ORAL - 225MG
CAPSULE, EXTENDED RELEASE;ORAL - 325MG
CAPSULE, EXTENDED RELEASE;ORAL - 425MG

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Also known as: 34183-22-7, Propafenone hcl, Rythmol, Rytmonorm, Arythmol, Pronon

Molecular Formula

C₂₁H₂₈ClNO₃

Molecular Weight

377.9 g/mol

InChI Key

XWIHRGFIPXWGEF-UHFFFAOYSA-N

FDA UNII

33XCH0HOCD

An antiarrhythmia agent that is particularly effective in ventricular arrhythmias. It also has weak beta-blocking activity.

1 2D Structure

Propafenone Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenylpropan-1-one;hydrochloride

2.1.2 InChI

InChI=1S/C21H27NO3.ClH/c1-2-14-22-15-18(23)16-25-21-11-7-6-10-19(21)20(24)13-12-17-8-4-3-5-9-17;/h3-11,18,22-23H,2,12-16H2,1H3;1H

2.1.3 InChI Key

XWIHRGFIPXWGEF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCNCC(COC1=CC=CC=C1C(=O)CCC2=CC=CC=C2)O.Cl

2.2 Other Identifiers

2.2.1 UNII

33XCH0HOCD

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Apo-propafenone

2. Arythmol

3. Baxarytmon

4. Cuxafenon

5. Fenoprain

6. Hydrochloride, Propafenone

7. Jutanorm

8. Nistaken

9. Norfenon

10. Pintoform

11. Prolecofen

12. Propafenon Al

13. Propafenon Hexal

14. Propafenon Minden

15. Propafenone

16. Propafenone Hydrochloride, (r)-isomer

17. Propafenone Hydrochloride, (s)-isomer

18. Propafenone, (+-)-isomer

19. Propafenone, (r)-isomer

20. Propafenone, (s)-isomer

21. Propamerck

22. Rythmol

23. Rytmo-puren

24. Rytmogenat

25. Rytmonorm

26. Sa 79

27. Sa-79

28. Sa79

2.3.2 Depositor-Supplied Synonyms

1. 34183-22-7

2. Propafenone Hcl

3. Rythmol

4. Rytmonorm

5. Arythmol

6. Pronon

7. Rythmol Sr

8. Propafenone (hydrochloride)

9. Propafenon Hydrochlorid

10. 1-(2-(2-hydroxy-3-(propylamino)propoxy)phenyl)-3-phenylpropan-1-one Hydrochloride

11. Sa-79 (hydrochloride)

12. 1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenylpropan-1-one Hydrochloride

13. 1-{2-[2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one Hydrochloride

14. 33xch0hocd

15. Nsc-758640

16. 1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenylpropan-1-one;hydrochloride

17. Mls000069682

18. Chebi:8466

19. Baxarytmon

20. Fenoprain

21. 2'-(2-hydroxy-3-(propylamino)propoxy)-3-phenylpropiophenone Hydrochloride

22. 1-propanone, 1-(2-(2-hydroxy-3-(propylamino)propoxy)phenyl)-3-phenyl-, Hydrochloride

23. Rhythmonorm

24. Smr000058493

25. 1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenyl-1-propanone Hydrochloride

26. Sa 79

27. Propafenon Hydrochlorid [german]

28. Sr-01000000192

29. Einecs 251-867-9

30. Unii-33xch0hocd

31. Wz 884

32. Propafenone, Hcl

33. Prestwick_831

34. Rythmol (tn)

35. Mfcd00079243

36. Propafenone Hydrochloride [usan:usp:jan]

37. Opera_id_1835

38. Schembl41412

39. Mls001148185

40. Mls002222267

41. Spectrum1503935

42. Chembl1201063

43. Hy-b0432a

44. Dtxsid101017233

45. Hms1569d19

46. Hms1922m16

47. Pharmakon1600-01503935

48. Bcp28548

49. Tox21_500919

50. Ccg-39061

51. Nsc758640

52. Propafenone Hydrochloride [mi]

53. Akos008901409

54. Propafenone Hydrochloride (jp17/usp)

55. Ks-5030

56. Lp00919

57. Nsc 758640

58. Propafenone Hydrochloride [jan]

59. Propafenone Hydrochloride [usan]

60. Propiophenone, 2'-(2-hydroxy-3-(propylamino)propoxy)-3-phenyl-, Hydrochloride

61. Ncgc00094230-01

62. Ncgc00094230-02

63. Ncgc00094230-03

64. Ncgc00094230-04

65. Ncgc00094230-05

66. Ncgc00261604-01

67. Propafenone Hydrochloride [mart.]

68. Propafenone Hydrochloride [vandf]

69. Ac-11360

70. Ac-33196

71. Propafenone Hydrochloride [usp-rs]

72. Propafenone Hydrochloride [who-dd]

73. Db-048579

74. Eu-0100919

75. Ft-0630579

76. P2301

77. En300-51034

78. D00640

79. P 4670

80. Propafenone Hydrochloride [ep Monograph]

81. Propafenone Hydrochloride [orange Book]

82. Propafenone Hydrochloride [usp Monograph]

83. 183p227

84. A822113

85. J-019481

86. Sr-01000000192-2

87. Sr-01000000192-6

88. Q27108087

89. Z802671518

90. 1-(2-[2-hydroxy-3-(propylamino)propoxy]phenyl)-3-phenyl-1propanone

91. 2'-(2-hydroxy-3-propylaminopropoxy)-3-phenylpropiophenone Hydrochloride

92. Propafenone Hydrochloride, European Pharmacopoeia (ep) Reference Standard

93. 1-[2-[2-oxidanyl-3-(propylamino)propoxy]phenyl]-3-phenyl-propan-1-one Hydrochloride

94. 2-hydroxy-3-[2-(3-phenylpropanoyl)phenoxy]-n-propylpropan-1-aminium Chloride

95. Hydron;1-[2-[2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenylpropan-1-one;chloride

96. Propafenone Hydrochloride, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₈ClNO₃
Molecular Weight	377.9 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	11
Exact Mass	377.1757714 g/mol
Monoisotopic Mass	377.1757714 g/mol
Topological Polar Surface Area	58.6 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	368
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 6
Drug Name	Propafenone hydrochloride
Drug Label	Propafenone hydrochloride is an antiarrhythmic drug supplied in scored, film-coated tablets of 150 and 225 mg for oral administration. Propafenone has some structural similarities to beta-blocking agents.Chemically, propafenone hydrochloride (HCl) is...
Active Ingredient	Propafenone hydrochloride
Dosage Form	Tablet; Capsule, extended release
Route	Oral
Strength	150mg; 300mg; 225mg; 425mg; 325mg
Market Status	Prescription
Company	Vintage Pharms; Ani Pharms; Par Pharm; Watson Labs; Mutual Pharm

2 of 6
Drug Name	Rythmol
PubMed Health	Propafenone (By mouth)
Drug Classes	Antiarrhythmic, Group IC
Drug Label	RYTHMOL SR (propafenone hydrochloride) is an antiarrhythmic drug supplied in extended-release capsules of 225, 325 and 425mg for oral administration.Chemically, propafenone hydrochloride is 2-[2-Hydroxy-3-(propylamino)-propoxy]-3-phenylpropiophe...
Active Ingredient	Propafenone hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	150mg; 300mg; 225mg
Market Status	Prescription
Company	Glaxosmithkline

3 of 6
Drug Name	Rythmol sr
PubMed Health	Propafenone (By mouth)
Drug Classes	Antiarrhythmic, Group IC
Drug Label	RYTHMOL SR (propafenone hydrochloride) is an antiarrhythmic drug supplied in extended-release capsules of 225, 325 and 425mg for oral administration.Chemically, propafenone hydrochloride is 2-[2-Hydroxy-3-(propylamino)-propoxy]-3-phenylpropiophe...
Active Ingredient	Propafenone hydrochloride
Dosage Form	Capsule, extended release
Route	Oral
Strength	225mg; 425mg; 325mg
Market Status	Prescription
Company	Glaxosmithkline

4 of 6
Drug Name	Propafenone hydrochloride
Drug Label	Propafenone hydrochloride is an antiarrhythmic drug supplied in scored, film-coated tablets of 150 and 225 mg for oral administration. Propafenone has some structural similarities to beta-blocking agents.Chemically, propafenone hydrochloride (HCl) is...
Active Ingredient	Propafenone hydrochloride
Dosage Form	Tablet; Capsule, extended release
Route	Oral
Strength	150mg; 300mg; 225mg; 425mg; 325mg
Market Status	Prescription
Company	Vintage Pharms; Ani Pharms; Par Pharm; Watson Labs; Mutual Pharm

5 of 6
Drug Name	Rythmol
PubMed Health	Propafenone (By mouth)
Drug Classes	Antiarrhythmic, Group IC
Drug Label	RYTHMOL SR (propafenone hydrochloride) is an antiarrhythmic drug supplied in extended-release capsules of 225, 325 and 425mg for oral administration.Chemically, propafenone hydrochloride is 2-[2-Hydroxy-3-(propylamino)-propoxy]-3-phenylpropiophe...
Active Ingredient	Propafenone hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	150mg; 300mg; 225mg
Market Status	Prescription
Company	Glaxosmithkline

6 of 6
Drug Name	Rythmol sr
PubMed Health	Propafenone (By mouth)
Drug Classes	Antiarrhythmic, Group IC
Drug Label	RYTHMOL SR (propafenone hydrochloride) is an antiarrhythmic drug supplied in extended-release capsules of 225, 325 and 425mg for oral administration.Chemically, propafenone hydrochloride is 2-[2-Hydroxy-3-(propylamino)-propoxy]-3-phenylpropiophe...
Active Ingredient	Propafenone hydrochloride
Dosage Form	Capsule, extended release
Route	Oral
Strength	225mg; 425mg; 325mg
Market Status	Prescription
Company	Glaxosmithkline

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

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.)

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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Antiarrhythmic [EPC]