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Disopyramide

Disopyramide

Synopsis, Chemistry

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Also known as: 22059-60-5, Norpace, Disopyramide phosphate salt, Rythmodan, Norpace cr, Sc 7031 phosphate

Molecular Formula

C₂₁H₃₂N₃O₅P

Molecular Weight

437.5 g/mol

InChI Key

CGDDQFMPGMYYQP-UHFFFAOYSA-N

FDA UNII

N6BOM1935W

A class I anti-arrhythmic agent (one that interferes directly with the depolarization of the cardiac membrane and thus serves as a membrane-stabilizing agent) with a depressant action on the heart similar to that of guanidine. It also possesses some anticholinergic and local anesthetic properties.

1 2D Structure

Disopyramide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[di(propan-2-yl)amino]-2-phenyl-2-pyridin-2-ylbutanamide;phosphoric acid

2.1.2 InChI

InChI=1S/C21H29N3O.H3O4P/c1-16(2)24(17(3)4)15-13-21(20(22)25,18-10-6-5-7-11-18)19-12-8-9-14-23-19;1-5(2,3)4/h5-12,14,16-17H,13,15H2,1-4H3,(H2,22,25);(H3,1,2,3,4)

2.1.3 InChI Key

CGDDQFMPGMYYQP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)N(CCC(C1=CC=CC=C1)(C2=CC=CC=N2)C(=O)N)C(C)C.OP(=O)(O)O

2.2 Other Identifiers

2.2.1 UNII

N6BOM1935W

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Diisopyramide

2. Disopyramide

3. Disopyramide Monohydrochloride

4. Disopyramide Phosphate (1:1)

5. Disopyramide Phosphate (1:1), (+-)-isomer

6. Disopyramide Phosphate (1:1), (r)-isomer

7. Disopyramide Phosphate (1:1), (s)-isomer

8. Disopyramide, (+-)-isomer

9. Disopyramide, (r)-isomer

10. Disopyramide, (s)-isomer

11. Disopyramide, D-tartrate (1:1), (s)-isomer

12. Disopyramide, L-tartrate (1:1), (r)-isomer

13. Disopyramide, L-tartrate (1:1), (s)-isomer

14. Disopyramide, L-tartrate (1:2), (+-)-isomer

15. Disopyramide, L-tartrate, (s)-isomer

16. Norpace

17. Palpitin

18. Palpitine

19. Rhythmodan

20. Ritmilen

21. Rythmilen

22. Sc 13957

23. Sc-13957

24. Sc13957

2.3.2 Depositor-Supplied Synonyms

1. 22059-60-5

2. Norpace

3. Disopyramide Phosphate Salt

4. Rythmodan

5. Norpace Cr

6. Sc 7031 Phosphate

7. Dirythmin Sa

8. Diso-duriles

9. Disopyramidephosphate

10. Einecs 244-756-1

11. Sc 7031 (phosphate)

12. Nsc-756744

13. Sc-13957

14. Sc-7031 Phosphate

15. Chebi:4658

16. N6bom1935w

17. 22059-60-5 (phosphate)

18. 2-(1-(ammoniocarbonyl)-3-(diisopropylammonio)-1-phenylpropyl)pyridinium Phosphate

19. Disopyramid Phosphate

20. 4-(diisopropylamino)-2-phenyl-2-(pyridin-2-yl)butanamide Phosphate

21. Sr-01000003039

22. Norpace (tn)

23. Sc 13957

24. Disopyramide (phosphate)

25. Unii-n6bom1935w

26. Schembl41810

27. Mls000028431

28. Spectrum1500261

29. Chembl1201020

30. Hms501i11

31. Dtxsid30944685

32. Disopyramide Phosphate (jan/usp)

33. Hms1920i14

34. Hms2094k15

35. Hms2234b16

36. Hms3259j21

37. Hms3261c04

38. Hms3369l05

39. Hms3652m20

40. Hms3885j07

41. Pharmakon1600-01500261

42. Disopyramide Phosphate [mi]

43. Xaa05960

44. Disopyramide Phosphate [jan]

45. Tox21_500411

46. Ccg-40209

47. Disopyramide Phosphate [usan]

48. Hy-12533a

49. Nsc756744

50. Disopyramide Phosphate [vandf]

51. 4-[di(propan-2-yl)amino]-2-phenyl-2-pyridin-2-ylbutanamide;phosphoric Acid

52. Alpha-(2-diisopropylaminoethyl)-alpha-phenyl-2-pyridineacetamide Phosphate

53. Disopyramide Phosphate [mart.]

54. Disopyramide Phosphate [usp-rs]

55. Disopyramide Phosphate [who-dd]

56. Lp00411

57. Nc00683

58. Nsc 756744

59. (+-)-alpha-(2-(diisopropylamino)ethyl)-alpha-phenyl-2-pyridineacetamide Phosphate (1:1)

60. 2-pyridineacetamide, Alpha-(2-(bis(1-methylethyl)amino)ethyl)-alpha-phenyl-, Phosphate

61. 2-pyridineacetamide, Alpha-(2-(bis(1-methylethyl)amino)ethyl)-alpha-phenyl-, Phosphate (1:1)

62. 2-pyridineacetamide, Alpha-(2-(diisopropylamino)ethyl)-alpha-phenyl-, Phosphate

63. Alpha-(2-(diisopropylamino)ethyl)-alpha-phenyl-2-pyridineacetamide Phosphate (1:1)

64. Ncgc00093836-01

65. Ncgc00093836-02

66. Ncgc00093836-03

67. Ncgc00093836-04

68. Ncgc00261096-01

69. 2-pyridineacetamide, Alpha-(2-(bis(1-methylethyl)amino)ethyl)-alpha-phenyl-, (+-)-, Phosphate (1:1)

70. Smr000058438

71. Db-045779

72. Disopyramide Phosphate [orange Book]

73. Disopyramide Phosphate [ep Monograph]

74. Disopyramide Phosphate [usan:usp:ban:jan]

75. Eu-0100411

76. Ft-0630479

77. S4143

78. Sw196836-3

79. Sw196836-4

80. Disopyramide Phosphate [usp Monograph]

81. C07740

82. D 6035

83. D00637

84. Sr-01000003039-2

85. Sr-01000003039-6

86. Q27106430

87. 4-(diisopropylamino)-2-phenyl-2-(2-pyridyl)butanamide

88. (r)-4-(diisopropylamino)-2-phenyl-2-(pyridin-2-yl)butanamide Phosphate

89. 4-[di(propan-2-yl)amino]-2-phenyl-2-pyridin-2-ylbutanamide,phosphoric Acid

90. 4-diisopropylamino-2-phenyl-2-(2-pyridyl)butyramide Phosphate

91. Disopyramide Phosphate, European Pharmacopoeia (ep) Reference Standard

92. Disopyramide Phosphate, United States Pharmacopeia (usp) Reference Standard

93. (+/-)-.alpha.-(2-(diisopropylamino)ethyl)-.alpha.-phenyl-2-pyridineacetamide Phosphate (1:1)

94. 2-pyridineacetamide, .alpha.-(2-(bis(1-methylethyl)amino)ethyl)-.alpha.-phenyl-, (+/-)-, Phosphate (1:1)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₃₂N₃O₅P
Molecular Weight	437.5 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	8
Exact Mass	437.20795813 g/mol
Monoisotopic Mass	437.20795813 g/mol
Topological Polar Surface Area	137 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	459
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	Disopyramide phosphate
PubMed Health	Disopyramide (By mouth)
Drug Classes	Antiarrhythmic, Group IA
Drug Label	Disopyramide Phosphate is an antiarrhythmic drug available for oral administration in capsules containing 100 mg or 150 mg of disopyramide base, present as the phosphate. The base content of the phosphate salt is 77.6%. The structural formula of Diso...
Active Ingredient	Disopyramide phosphate
Dosage Form	Capsule
Route	Oral
Strength	eq 100mg base; eq 150mg base
Market Status	Prescription
Company	Watson Labs; Teva

2 of 6
Drug Name	Norpace
Active Ingredient	Disopyramide phosphate
Dosage Form	Capsule
Route	Oral
Strength	eq 100mg base; eq 150mg base
Market Status	Prescription
Company	Gd Searle

3 of 6
Drug Name	Norpace cr
PubMed Health	Disopyramide (By mouth)
Drug Classes	Antiarrhythmic, Group IA
Drug Label	Norpace (disopyramide phosphate) is an antiarrhythmic drug available for oral administration in immediate-release and controlled-release capsules containing 100 mg or 150 mg of disopyramide base, present as the phosphate. The base content of the phos...
Active Ingredient	Disopyramide phosphate
Dosage Form	Capsule, extended release
Route	Oral
Strength	eq 100mg base; eq 150mg base
Market Status	Prescription
Company	Gd Searle

4 of 6
Drug Name	Disopyramide phosphate
PubMed Health	Disopyramide (By mouth)
Drug Classes	Antiarrhythmic, Group IA
Drug Label	Disopyramide Phosphate is an antiarrhythmic drug available for oral administration in capsules containing 100 mg or 150 mg of disopyramide base, present as the phosphate. The base content of the phosphate salt is 77.6%. The structural formula of Diso...
Active Ingredient	Disopyramide phosphate
Dosage Form	Capsule
Route	Oral
Strength	eq 100mg base; eq 150mg base
Market Status	Prescription
Company	Watson Labs; Teva

5 of 6
Drug Name	Norpace
Active Ingredient	Disopyramide phosphate
Dosage Form	Capsule
Route	Oral
Strength	eq 100mg base; eq 150mg base
Market Status	Prescription
Company	Gd Searle

6 of 6
Drug Name	Norpace cr
PubMed Health	Disopyramide (By mouth)
Drug Classes	Antiarrhythmic, Group IA
Drug Label	Norpace (disopyramide phosphate) is an antiarrhythmic drug available for oral administration in immediate-release and controlled-release capsules containing 100 mg or 150 mg of disopyramide base, present as the phosphate. The base content of the phos...
Active Ingredient	Disopyramide phosphate
Dosage Form	Capsule, extended release
Route	Oral
Strength	eq 100mg base; eq 150mg base
Market Status	Prescription
Company	Gd Searle

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]