Milrinone

HCID 4197CAS 78415-72-2

Basic information

Standard SMILES
Cc1[nH]c(=O)c(C#N)cc1-c1ccncc1
InChIKey
PZRHRDRVRGEVNW-UHFFFAOYSA-N
Molecular formula
C12H9N3O
Average molar mass
211.22 g/mol
Monoisotopic mass
211.07456191

Overview

Milrinone is a member of the class of bipyridines that is 2-pyridone which is substituted at positions 3, 5, and 6 by cyano, pyrid-4-yl, and methyl groups, respectively. It is used (particularly intravenously, as the lactate) for the short-term management of severe heart failure. It has a role as a vasodilator agent, a cardiotonic drug, a platelet aggregation inhibitor and an EC 3.1.4.17 (3',5'-cyclic-nucleotide phosphodiesterase) inhibitor. It is a nitrile, a pyridone and a member of bipyridines.

Names & identifiers

Preferred name
Milrinone
IUPAC
6-methyl-2-oxo-5-pyridin-4-yl-1H-pyridine-3-carbonitrile
English name
Milrinone
Molecular formula
C12H9N3O
Molecular weight
211.22

Names & synonyms

milrinone78415-72-2MilrilaMilrinonaMilrinonumWin-47203-21,6-Dihydro-2-methyl-6-oxo(3,4'-bipyridine)-5-carbonitrileDTXSID50233246-methyl-2-oxo-5-(pyridin-4-yl)-1,2-dihydropyridine-3-carbonitrileJU9YAX04C7WIN 47203NSC-760072
Show more names
PrimacorMilirinoneMilrinone USPYM-018Minongwin47203MirinoneCorotrope
WIN 47,203-2(3,4'-BIPYRIDINE)-5-CARBONITRILE, 1,6-DIHYDRO-2-METHYL-6-OXO-DTXCID103324CorotropCHEBI:50693(3,4'-Bipyridine)-5-carbonitrile, 6-dihydro-2-methyl-6-oxo-[3,4'-Bipyridine]-5-carbonitrile, 1,6-dihydro-2-methyl-6-oxo-Lactate, Milrinone

Database identifiers

CAS
78415-72-2
PubChem CID
4197
DTXSID
DTXSID5023324
ChEMBL
CHEMBL189
ChEBI
CHEBI:50693
UNII
JU9YAX04C7
EC Number
278-903-6
Nikkaji
J23.655A

Properties

Computed structural properties

XLogP
0
Topological polar surface area
65.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
16

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

LogP · 2 items

0.4

0.42

Solubility · 2 items

<1 mg/mL

2.09e-01 g/L

Human DrugsPharmaceuticals
Melting Point · 2 items

>300 °C

> 300 °C

Physical DescriptionSolid

Physicochemical properties

Melting point
3000 C · >3000C
Boiling point
350.9 °C · 350.9°C (rough estimate)
Density
1.1922 · 1.1922 (rough estimate)
refractive index
1.57 · 1.5700 (estimate)
storage temp.
2 · 2-8°C
solubility
10 mg/mL · DMSO: >10 mg/mL

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301+H311+H331 (38.4%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 73 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxicology

Adverse Effects · 1 item

The most feared adverse effect of milrinone is its potential to induce hemodynamic changes and arrhythmias. Milrinone may cause ventricular tachyarrhythmia, leading to cardiac ischemia or sudden cardiac death. These changes are not shown to follow a dose-dependent relationship. Milrinone can cause an increase in venous vessel capacitance, leading to decreased preload and manifesting as headaches, syncope, and severe hypotension. Unlike tachyarrhythmias, hypotension occurs in a dose-dependent relationship.

Toxicity Summary · 1 item

Cardiovascular toxicity is primarily seen in chronically milrinone patients and manifests as tachyarrhythmias and sudden cardiac death. At high dosing, patients may also experience hypotension and syncope. Milrinone had a previous use as an oral formulation for outpatient use in patients with NYHA class III and IV chronic heart failure (CHF) to improve symptoms and decrease the frequency of hospital admissions. However, this practice was discontinued following the PROMISE trial in 1991 due to safety concerns. This double-blinded clinical trial assessed patients with CHF class III/IV placed on milrinone or placebo and ended early due to increased mortality in the milrinone group secondary to ventricular tachyarrhythmias and sudden cardiac death.

Safety data

wgk
3
rtecs
DW1762000
ridadr
UN 2811 6.1/PG 3
hs_code
29337900
risk_code
23/24/25-26/27/28
Signal word
Danger

Chemistry & industry

Pharmacology

ATC Code · 3 items

C01CE02

C - Cardiovascular system

QC - Cardiovascular system

Protein BindingMilrinone is approximately 70% bound to human plasma proteins.
Pharmacodynamics · 1 item

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.

Mechanism of Action · 1 item

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 β-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 IC<sub>50</sub> value of between 0.66 and 1.3 μM. 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 β-adrenergic receptors, it is effective in patients who have downregulated or otherwise desensitized β-adrenergic receptors and can be administered together with β-agonists/antagonists.

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

Uses & manufacturing

UsesUse (kg) in USA (2002): 10
Use ClassificationPharmaceuticals
Applications · 8 items

UsesNew non-glycosides non-catecholamines cardiac drug , its function is similar to amrinone ,positive inotropic effect is strong and about 20 to 50 times of amrinone, and it has significant effect on expanding smooth muscle,it can reduce the load on the heart, it can also improve kidney and muscle blood supply. Oral and intravenous are valid, no serious adverse reactions. It is used For severe heart failure such as chronic heart failure and congestive heart failure.

DescriptionMilrinone, an inhibitor of phosphodiesterase selective for fraction III PDE, exerts a positive inotropic effect on the heart as well as a peripheral vasodilatory effect. Milrinone given intravenously produces significant improvements on cardiac output, pulmonary capillary wedge pressure and vascular resistance without significant effects on the heart rate.

DescriptionMilrinone is an inhibitor of type 3 phosphodiesterases (PDEs), inhibiting recombinant PDE3A and PDE3B with IC50 values of 0.45 and 1 μM, respectively. It is selective for PDE3 over PDE1, PDE2, PDE4, PDE5, and PDE7 (IC50s = 263, >300, 17.5, 49.1, and 58.3 μM, respectively). Milrinone (0.1-1 mg/kg) has positive inotropic effects, increasing cardiac contractile force in anesthetized dogs with a concomitant increase in heart rate but not blood pressure. It also increases contractile force in models of propranolol- and verapamil-induced heart failure in anesthetized dogs when administered at an initial dose of 30 μg/kg followed by a continuous 3 μg/kg per minute infusion. Milrinone has vasodilatory effects as well, decreasing mean aortic pressure and increasing venous compliance in anesthetized dogs when administered at an initial dose of 10 μg/kg followed by a continuous 1.7-2.4 μg/kg per minute infusion. Formulations containing milrinone have been used in the treatment of heart failure.

Usesantidepressant, 5HT reuptake inhibitor

Usesbronchodilator

UsesSelective phosphodiesterase inhibitor with vasodilating and positive inotropic activity. Cardiotonic

UsesIt is used (particularly intravenously, as the lactate) for the short-term management of severe heart failure. Milrinone inhibits the action of phosphodiesterase-3 preventing degradation of cAMP. The corresponding increase in cAMP levels leads to increased activation of protein kinase A. It is a selective phosphodiesterase inhibitor with vasodilating and positive inotropic activity.

General DescriptionMilrinone, 1,6-dihydro-2-methyl-6-oxo-3,4'-bipyridine-5-carbonitrile (Primacor), is another dipyridinephosphodiesterase F-III inhibitor that possesses pharmacologicalproperties similar to those of amrinone. The inhibitionof the degradation of cAMP results in an increase in the cardiacmuscle’s force of contraction.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
苏州法姆医药科技有限公司0510-88771160 18051901298 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Milrinone is a member of the class of bipyridines that is 2-pyridone which is substituted at positions 3, 5, and 6 by cyano, pyrid-4-yl, and methyl groups, respectively. It is used (particularly intravenously, as the lactate) for the short-term management of severe heart failure. It has a role as an EC 3.1.4.17 (3',5'-cyclic-nucleotide phosphodiesterase) inhibitor, a platelet aggregation inhibitor, a vasodilator agent and a cardiotonic drug. It is a pyridone, a nitrile and a member of bipyridines.

Related reactions

6 records

Linked notes

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