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Also known as: 78415-72-2, Primacor, Milrinona, Milrinonum, Milrila, 2-methyl-6-oxo-1,6-dihydro-[3,4'-bipyridine]-5-carbonitrile
Molecular Formula
C12H9N3O
Molecular Weight
211.22  g/mol
InChI Key
PZRHRDRVRGEVNW-UHFFFAOYSA-N
FDA UNII
JU9YAX04C7

Milrinone
A positive inotropic cardiotonic agent with vasodilator properties. It inhibits cAMP phosphodiesterase type 3 activity in myocardium and vascular smooth muscle. Milrinone is a derivative of amrinone and has 20-30 times the inotropic potency of amrinone.
Milrinone is a Phosphodiesterase 3 Inhibitor. The mechanism of action of milrinone is as a Phosphodiesterase 3 Inhibitor.
1 2D Structure

Milrinone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
6-methyl-2-oxo-5-pyridin-4-yl-1H-pyridine-3-carbonitrile
2.1.2 InChI
InChI=1S/C12H9N3O/c1-8-11(9-2-4-14-5-3-9)6-10(7-13)12(16)15-8/h2-6H,1H3,(H,15,16)
2.1.3 InChI Key
PZRHRDRVRGEVNW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=C(C=C(C(=O)N1)C#N)C2=CC=NC=C2
2.2 Other Identifiers
2.2.1 UNII
JU9YAX04C7
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Corotrop

2. Corotrope

3. Lactate, Milrinone

4. Milrinone Lactate

5. Primacor

6. Win 47203

7. Win-47203

8. Win47203

2.3.2 Depositor-Supplied Synonyms

1. 78415-72-2

2. Primacor

3. Milrinona

4. Milrinonum

5. Milrila

6. 2-methyl-6-oxo-1,6-dihydro-[3,4'-bipyridine]-5-carbonitrile

7. Win 47203

8. 6-methyl-2-oxo-5-pyridin-4-yl-1h-pyridine-3-carbonitrile

9. 1,6-dihydro-2-methyl-6-oxo(3,4'-bipyridine)-5-carbonitrile

10. Win-47203-2

11. 3-cyano-6-methyl-5-(4-pyridyl)-2-pyridone

12. Mfcd00133539

13. 2-methyl-6-oxo-1,6-dihydro-3,4'-bipyridine-5-carbonitrile

14. 6-methyl-2-oxo-5-(pyridin-4-yl)-1,2-dihydropyridine-3-carbonitrile

15. Corotrope

16. 1,6-dihydro-2-methyl-6-oxo-(3,4'-bipyridine)-5-carbonitrile

17. Chembl189

18. Nsc-760072

19. Ju9yax04c7

20. Win 47,203-2

21. Chebi:50693

22. (3,4'-bipyridine)-5-carbonitrile, 1,6-dihydro-2-methyl-6-oxo-

23. Milrinonum [latin]

24. Ncgc00015675-08

25. Ncgc00164390-01

26. Milrinona [spanish]

27. [3,4'-bipyridine]-5-carbonitrile, 1,6-dihydro-2-methyl-6-oxo-

28. Cas-78415-72-2

29. Dsstox_cid_3324

30. Dsstox_rid_76978

31. Dsstox_gsid_23324

32. 2-hydroxy-6-methyl-5-pyridin-4-ylpyridine-3-carbonitrile

33. 1,6-dihydro-2-methyl-6-oxo-[3,4'-bipyridine]-5-carbonitrile

34. Ym 018

35. Smr000058475

36. Milrila (tn)

37. Win 47203-2

38. Ccris 3795

39. Sr-01000075524

40. Einecs 278-903-6

41. Unii-ju9yax04c7

42. Brn 3546821

43. Milrinone [usan:usp:inn:ban]

44. Milrinone- Bio-x

45. Milrinone(primacor)

46. 6-methyl-5-(4-pyridyl)-2-pyridone-3-carbonitrile

47. Milrinone (primacor)

48. Tocris-1504

49. 111ge027

50. Milrinone [inn]

51. Milrinone [jan]

52. (3,4'-bipyridine)-5-carbonitrile, 6-dihydro-2-methyl-6-oxo-

53. Milrinone [mi]

54. Milrinone [usan]

55. 1,2-dihydro-6-methyl-2-oxo-5-(4-pyridinyl)nicotinonitrile

56. Prestwick0_001065

57. Prestwick1_001065

58. Prestwick2_001065

59. Prestwick3_001065

60. Lopac-m-4659

61. Milrinone [vandf]

62. M1663

63. Milrinone [mart.]

64. M 4659

65. (non-labelled)milrinone-d3

66. Milrinone [usp-rs]

67. Milrinone [who-dd]

68. Milrinone (jan/usp/inn)

69. Lopac0_000737

70. Schembl36947

71. Bspbio_001050

72. Mls000028818

73. Mls001424052

74. Mls006011946

75. Bidd:gt0197

76. Spbio_002965

77. Bpbio1_001156

78. Gtpl5225

79. Schembl8309385

80. Dtxsid5023324

81. Bdbm15296

82. Milrinone [usp Monograph]

83. Hms1571e12

84. Hms2051l10

85. Hms2090j14

86. Hms2098e12

87. Hms2234a23

88. Hms3262c16

89. Hms3267p12

90. Hms3370h18

91. Hms3393l10

92. Hms3656g06

93. Hms3715e12

94. Hms3742g09

95. Pharmakon1600-01505489

96. Amy40564

97. Bcp02956

98. Zinc9224016

99. Tox21_112113

100. Tox21_400069

101. Tox21_500737

102. Milrinone, >=97% (tlc), Powder

103. Nsc760072

104. S2484

105. Milrinone - Cas 78415-72-2

106. 2-methyl-6-oxo-1,6-dihydro-3,4'-bipyridine-5-carbonitrile (milrinone)

107. Akos015836135

108. Tox21_112113_1

109. Ac-4730

110. Bcp9000926

111. Ccg-101020

112. Ccg-204822

113. Cs-1367

114. Db00235

115. Ks-1440

116. Lp00737

117. Nc00270

118. Nsc 760072

119. Sdccgsbi-0050715.p002

120. Ncgc00015675-01

121. Ncgc00015675-02

122. Ncgc00015675-03

123. Ncgc00015675-04

124. Ncgc00015675-05

125. Ncgc00015675-06

126. Ncgc00015675-07

127. Ncgc00015675-09

128. Ncgc00015675-11

129. Ncgc00015675-24

130. Ncgc00025189-01

131. Ncgc00025189-02

132. Ncgc00025189-03

133. Ncgc00261422-01

134. Bm164671

135. Hy-14252

136. Smr004703527

137. Sy028050

138. Bcp0726000256

139. Ab00514027

140. Eu-0100737

141. Ft-0630859

142. Sw197308-3

143. C07224

144. D00417

145. Ab00514027-02

146. Ab00514027-03

147. Ab00514027_04

148. Ab00514027_05

149. Ab00597139-08

150. 415m722

151. A839417

152. Q847399

153. Sr-01000075524-1

154. Sr-01000075524-3

155. Sr-01000075524-4

156. Sr-01000075524-6

157. W-104284

158. Brd-k67080878-001-05-5

159. Z1522568219

160. 1,2-dihydro-6-methyl-2-oxo-5-(4 -pyridinyl)nicotinonitrile

161. 2-methyl-6-oxo-1,6-dihydro-[3,4']bipyridinyl-5-carbonitrile

162. Milrinone, United States Pharmacopeia (usp) Reference Standard

163. 1,2-dihydro-6-methyl-2-oxo-5-(4-pyridinyl)-nicotinonitrile

164. 6-methyl-2-oxidanylidene-5-pyridin-4-yl-1h-pyridine-3-carbonitrile

165. 1,6-dihydro-2-methyl-6-oxo-(3,4 Inverted Exclamation Mark -bipyridine)-5-carbonitrile

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 211.22 g/mol
Molecular Formula C12H9N3O
XLogP30
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass211.074561919 g/mol
Monoisotopic Mass211.074561919 g/mol
Topological Polar Surface Area65.8 Ų
Heavy Atom Count16
Formal Charge0
Complexity419
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Milrinone is indicated for the short-term (48 hours or less) treatment of patients with acute decompensated heart failure. Milrinone administration should occur together with close monitoring using appropriate electrocardiographic equipment and should occur in a facility equipped for the immediate treatment of potential cardiac events, including ventricular arrhythmias.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Milrinone is a bipyridine derivative with positive inotropic and lusitropic effects that also results in peripheral vasodilation with minimal chronotropic effects over a therapeutic range of 100 to 300 ng/mL. As such, milrinone is used in decompensated congestive heart failure. Studies have demonstrated that milrinone exhibits sigmoidal effects, such that increasing milrinone plasma concentrations beyond a certain level results in no further hemodynamic changes. Despite milrinone's benefits, both intravenous and oral use has been associated with increased frequency of ventricular arrhythmias, and long-term oral use has been associated with an increased risk of sudden death; in general, there are no data to support the safety or efficacy of milrinone use beyond 48 hours and patients should be monitored closely for cardiac dysfunction. Also, as milrinone is primarily excreted renally, dose adjustments may be required in patients with impaired renal function.


5.2 MeSH Pharmacological Classification

Phosphodiesterase 3 Inhibitors

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


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.)


Platelet Aggregation Inhibitors

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
MILRINONE
5.3.2 FDA UNII
JU9YAX04C7
5.3.3 Pharmacological Classes
Mechanisms of Action [MoA] - Phosphodiesterase 3 Inhibitors
5.4 ATC Code

C01CE02

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


C - Cardiovascular system

C01 - Cardiac therapy

C01C - Cardiac stimulants excl. cardiac glycosides

C01CE - Phosphodiesterase inhibitors

C01CE02 - Milrinone


5.5 Absorption, Distribution and Excretion

Absorption

When administered as an IV bolus dose of 10-100 g/kg, milrinone induces hemodynamic effects within 60 seconds reaching a peak effect by 2-5 minutes. The plasma AUC is significantly dose-dependent.


Route of Elimination

Milrinone is primarily excreted in the urine, with 60% of a dose recovered after two hours and 90% within eight hours. Approximately 83% of milrinone recovered in urine is unchanged while 12% is present as the main O-glucuronide metabolite.


Volume of Distribution

Milrinone administered intravenously to congestive heart failure patients had a volume of distribution of 0.38 L/kg (injections between 12.5-125 g/kg) and 0.45 L/kg (infusions between 0.2-0.7 g/kg/min.


Clearance

Milrinone administered intravenously to congestive heart failure patients had a clearance of 0.13 L/kg/hr (injections between 12.5-125 g/kg) and 0.14 L/kg/hr (infusions between 0.2-0.7 g/kg/min.


5.6 Metabolism/Metabolites

Animal studies suggest that two oxidative pathways are involved in milrinone metabolism, albeit only involving a small proportion of the administered dose. The major metabolite is the O-glucuronide metabolite.


5.7 Biological Half-Life

Milrinone administered intravenously to congestive heart failure patients had a mean terminal elimination half-life of 2.3 hours (injections between 12.5-125 g/kg) and 2.4 hours (infusions between 0.2-0.7 g/kg/min.


5.8 Mechanism of Action

Heart failure is a condition characterized by the heart's inability to provide adequate perfusion to the peripheral tissues, resulting in systemic symptoms including pulmonary, gastrointestinal, renal, and cerebral dysfunction. Although the biochemical and physiological processes underlying heart failure complex and variable, one such physiological response regulated by the sympathetic nervous system involves the eventual downregulation of cardiac -receptors, decreased catecholamine sensitivity, and a corresponding decrease in adenylyl-cyclase-mediated signalling pathways. Increased intracellular cAMP, mainly acting through protein kinase A, increases sarcolemmal calcium release through L-type calcium channels as well as calcium re-uptake mediated by phospholamban and troponin I; these actions correspond to positive inotropic and lusitropic effects, respectively. Milrinone is a partial competitive inhibitor of phosphodiesterase III (PDE-III), with a measured IC50 value of between 0.66 and 1.3 M. As a PDE-III inhibitor, milrinone results in an increase in intracellular cAMP, responsible for its pharmacological effects, including positive inotropy, positive lusitropy, and vasodilation. As milrinone affects cAMP levels through PDE-III and not through -adrenergic receptors, it is effective in patients who have downregulated or otherwise desensitized -adrenergic receptors and can be administered together with -agonists/antagonists.


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04-May-2021
05-Aug-2024
KGS
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Average Price (USD/KGS)

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Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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