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
Show more names
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
- Formal charge
- 0
- Complexity
- 419
Experimental & physicochemical properties
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
LogP
0.4
0.42
Solubility
<1 mg/mL
2.09e-01 g/L
Melting Point
>300 °C
> 300 °C
Collision Cross Section
157.1 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID5023324]
150.4 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
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
- form
- powder
- pka
- 7.21 · 7.21±0.10(Predicted)
- color
- off-white
- Water Solubility
- Soluble in DMSO. Insoluble in water.
- Merck
- 14 · 14,6197
- Stability
- Stable. Incompatible with strong oxidizing agents.
- 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)
- InChIKey
- FYEJSUDMDUIMKJ-UHFFFAOYSA-N
- SMILES
- C1(C)NC(=O)C(C#N)=CC=1C1C=CN=CC=1
- CAS DataBase Reference
- 78415 · 78415-72-2(CAS DataBase Reference)
- FDA UNII
- 9 YAX04C7 · JU9YAX04C7
- ATC code
- 1 CE02 · C01CE02
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301
- Precautionary statements
- 301 · P301+P330+P331+P310
- Hazard Codes
- T,T+
- Risk Statements
- 23 · 23/24/25-26/27/28
- Safety Statements
- 36 · 36/37/39-45-22
- RIDADR
- 2811 · UN 2811 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 1762000 · DW1762000
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- HS Code
- 29337900 · 29337900
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 Oral · Acute Tox. 3 Oral
Safety & regulation
GHS classification
GHS Classification
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
Toxicology
Adverse Effects
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
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
- Symbol(GHS)
- GHS06
- hazard_code
- T,T+
- safety_code
- 36/37/39-45-22
- hazard_class
- 6.1(b)
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P301+P330+P331+P310
Chemistry & industry
Pharmacology
ATC Code
C01CE02
C - Cardiovascular system
QC - Cardiovascular system
Pharmacodynamics
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
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.
FDA Pharmacological Classification
JU9YAX04C7
MILRINONE
Established Pharmacologic Class [EPC] - Phosphodiesterase 3 Inhibitor
Mechanisms of Action [MoA] - Phosphodiesterase 3 Inhibitors
Milrinone is a Phosphodiesterase 3 Inhibitor. The mechanism of action of milrinone is as a Phosphodiesterase 3 Inhibitor.
MeSH Pharmacological Classification
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).
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.
Drugs used to cause dilation of the blood vessels.
Compounds that specifically inhibit PHOSPHODIESTERASE 3.
Absorption, Distribution and Excretion
When administered as an IV bolus dose of 10-100 μg/kg, milrinone induces hemodynamic effects within 60 seconds reaching a peak effect by 2-5 minutes. The plasma AUC is significantly dose-dependent.
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.
Milrinone administered intravenously to congestive heart failure patients had a volume of distribution of 0.38 L/kg (injections between 12.5-125 μg/kg) and 0.45 L/kg (infusions between 0.2-0.7 μg/kg/min.
Milrinone administered intravenously to congestive heart failure patients had a clearance of 0.13 L/kg/hr (injections between 12.5-125 μg/kg) and 0.14 L/kg/hr (infusions between 0.2-0.7 μg/kg/min.
Uses & manufacturing
Applications
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.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
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
Linked notes
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