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Chemistry

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Also known as: 60719-84-8, Inamrinone, Wincoram, Inocor, Cordemcura, Cartonic

Molecular Formula

C₁₀H₉N₃O

Molecular Weight

187.20 g/mol

InChI Key

RNLQIBCLLYYYFJ-UHFFFAOYSA-N

FDA UNII

JUT23379TN

A positive inotropic cardiotonic (CARDIOTONIC AGENTS) with vasodilator properties, phosphodiesterase 3 inhibitory activity, and the ability to stimulate calcium ion influx into the cardiac cell.

1 2D Structure

Amrinone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-amino-5-pyridin-4-yl-1H-pyridin-2-one

2.1.2 InChI

InChI=1S/C10H9N3O/c11-9-5-8(6-13-10(9)14)7-1-3-12-4-2-7/h1-6H,11H2,(H,13,14)

2.1.3 InChI Key

RNLQIBCLLYYYFJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CN=CC=C1C2=CNC(=O)C(=C2)N

2.2 Other Identifiers

2.2.1 UNII

JUT23379TN

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-amino-(3,4'-bipyridine)-6(1h)-one

2. Amrinon

3. Cordemcura

4. Inocor

5. Win 40680

6. Win-40680

7. Win40680

8. Wincoram

2.3.2 Depositor-Supplied Synonyms

1. 60719-84-8

2. Inamrinone

3. Wincoram

4. Inocor

5. Cordemcura

6. Cartonic

7. Amcoral

8. Amrinonum [inn-latin]

9. Vesistol

10. 5-amino-[3,4'-bipyridin]-6(1h)-one

11. Amrinona [inn-spanish]

12. 3-amino-5-(4-pyridinyl)-2(1h)-pyridinone

13. Win-40680

14. Win 40680

15. 3-amino-5-pyridin-4-yl-1h-pyridin-2-one

16. 5-amino-(3,4'-bipyridin)-6(1h)-one

17. Awd 08-250

18. [3,4'-bipyridin]-6(1h)-one, 5-amino-

19. Amrinone [inn]

20. 5-amino-3,4'-bipyridin-6(1h)-one

21. Amrinone Lactate

22. Mls000069829

23. 5-amino(3,4'-bipyridin)-6(1h)-one

24. Nsc-759805

25. (3,4'-bipyridin)-6(1h)-one, 5-amino-

26. Smr000058850

27. Chembl12856

28. Jut23379tn

29. C01ce01

30. 3-amino-5-pyridin-4-ylpyridin-2-ol

31. 3-amino-5-(pyridin-4-yl)pyridin-2-ol

32. 5-amino[3,4'-bipyridin]-6(1h)-one

33. Ncgc00164379-01

34. Amrinona

35. Amrinonum

36. Cas-60719-84-8

37. Dsstox_cid_2603

38. Dsstox_rid_76655

39. Dsstox_gsid_22603

40. Inamrinone (usp)

41. Amcoral (tn)

42. Ccris 3794

43. 3-amino-5-(pyridin-4-yl)pyridin-2(1h)-one

44. Amrinone (jan/inn)

45. Inamrinone [usan:usp]

46. Einecs 262-390-0

47. Brn 0744819

48. Unii-jut23379tn

49. Prestwick_44

50. Amrinone,(s)

51. Mfcd00083228

52. Spectrum_001350

53. Amrinone [jan]

54. Amrinone [mi]

55. Amrinone [vandf]

56. Opera_id_1054

57. Prestwick0_000800

58. Prestwick1_000800

59. Prestwick2_000800

60. Prestwick3_000800

61. Spectrum2_001980

62. Spectrum3_000956

63. Spectrum4_001069

64. Spectrum5_000999

65. Inamrinone [usan]

66. Amrinone [mart.]

67. Inamrinone [vandf]

68. Amrinone [usp-rs]

69. Amrinone [who-dd]

70. Cid_3698

71. Schembl44012

72. Bspbio_000940

73. Kbiogr_001398

74. Kbioss_001830

75. 5-25-15-00181 (beilstein Handbook Reference)

76. Mls001074083

77. Divk1c_000136

78. Spectrum1503084

79. Spbio_002139

80. Spbio_002879

81. Bpbio1_001034

82. Chebi:2686

83. Gtpl7202

84. Dtxsid9022603

85. Schembl13457017

86. Bdbm34651

87. Hms500g18

88. Kbio1_000136

89. Kbio2_001830

90. Kbio2_004398

91. Kbio2_006966

92. Kbio3_002052

93. Inamrinone [usp Impurity]

94. Ninds_000136

95. Hms1570o22

96. Hms2097o22

97. Hms2234f12

98. Hms3264e16

99. Hms3369j10

100. Hms3714o22

101. Inamrinone [usp Monograph]

102. Pharmakon1600-01503084

103. Bcp12764

104. Hy-b1294

105. Zinc8673078

106. Tox21_112110

107. Tox21_301847

108. Ccg-39487

109. Nsc759805

110. Stk590307

111. Akos005512516

112. Tox21_112110_1

113. Db01427

114. Ks-5178

115. Nsc 759805

116. Cid 5281003

117. Idi1_000136

118. Ncgc00016896-01

119. Ncgc00016896-02

120. Ncgc00016896-03

121. Ncgc00016896-04

122. Ncgc00016896-06

123. Ncgc00095984-01

124. Ncgc00255137-01

125. Ac-12186

126. Ac-33137

127. Ba166404

128. 5-amino(3,4'-bipyridine)-6-(1h)-one

129. 5-amino-(3,4?-bipyridin)-6(1h)-one

130. 3-amino-5-(4-pyridinyl)-2(1h)pyridinone

131. 3-azanyl-5-pyridin-4-yl-1h-pyridin-2-one

132. Cs-0013064

133. Ft-0601595

134. 5-amino-3,4'-bipyridyl-6(1h)-one

135. C75837

136. D00231

137. Ab00052312-04

138. Ab00052312_05

139. 3-amino-5-(4-pyridinyl)-1,2-dihydro-2-pyridone

140. 719a848

141. A832852

142. Q422724

143. Sr-00000002445

144. Sr-00000002445-2

145. W-105234

146. 3-amino-5-(pyridin-4-yl)-1,2-dihydropyridin-2-one

147. Brd-k45924332-001-04-4

148. Brd-k45924332-001-07-7

149. Amrinone, United States Pharmacopeia (usp) Reference Standard

150. 216151-27-8

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₉N₃O
Molecular Weight	187.20 g/mol
XLogP3	-0.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	187.074561919 g/mol
Monoisotopic Mass	187.074561919 g/mol
Topological Polar Surface Area	68 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	301
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Used in the treatment of congestive heart failure.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Amrinone is a positive inotropic cardiotonic with vasodilator properties, phosphodiesterase inhibitory activity, and the ability to stimulate calcium ion influx into the cardiac cell.

5.2 MeSH Pharmacological Classification

Calcium Channel Blockers

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

Cardiotonic Agents

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE). (See all compounds classified as Cardiotonic Agents.)

Phosphodiesterase 3 Inhibitors

Compounds that specifically inhibit PHOSPHODIESTERASE 3. (See all compounds classified as Phosphodiesterase 3 Inhibitors.)

5.3 ATC Code

C - Cardiovascular system

C01 - Cardiac therapy

C01C - Cardiac stimulants excl. cardiac glycosides

C01CE - Phosphodiesterase inhibitors

C01CE01 - Amrinone

5.4 Absorption, Distribution and Excretion

Route of Elimination

The primary route of excretion in man is via the urine as both inamrinone and several metabolites (N-glycolyl, N-acetate, O-glucuronide and N-glucuronide).

Volume of Distribution

1.2 L/kg [normal volunteers]

5.5 Metabolism/Metabolites

Hepatic.

5.6 Biological Half-Life

5 to 8 hours

5.7 Mechanism of Action

Amrinone is a phosphodiesterase inhibitor (PDE3), resulting in increased cAMP and cGMP which leads to an increase in the calcium influx like that caused by beta-agonists resulting in increased inotropic effect.

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