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Milrinone
Identification
- Name
- Milrinone
- Accession Number
- DB00235
- Description
A positive inotropic cardiotonic agent with vasodilator properties. It inhibits cAMP phosphodiesterase activity in myocardium and vascular smooth muscle. Milrinone is a derivative of amrinone and has 20-30 times the ionotropic potency of amrinone.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Milrinone (DB00235)
- Weight
- Average: 211.2194
Monoisotopic: 211.074561925 - Chemical Formula
- C12H9N3O
- Synonyms
- 1,6-Dihydro-2-methyl-6-oxo(3,4'-bipyridine)-5-carbonitrile
- Milrinona
- Milrinone
- Milrinonum
- External IDs
- WIN 47,203-2
Pharmacology
- Indication
Indicated for the treatment of congestive heart failure.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Milrinone, a synthetic dimethylxanthine derivative structurally related to theophylline and caffeine, is used in the treatment of peripheral vascular diseases and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic neuropathy.
- Mechanism of action
Milrinone inhibits erythrocyte phosphodiesterase, resulting in an increase in erythrocyte cAMP activity. Subsequently, the erythrocyte membrane becomes more resistant to deformity. Along with erythrocyte activity, Milrinone also decreases blood viscosity by reducing plasma fibrinogen concentrations and increasing fibrinolytic activity.
Target Actions Organism AcGMP-inhibited 3',5'-cyclic phosphodiesterase A inhibitorHumans - Absorption
Milrinone is rapidly and almost completely absorbed after oral administration. Bioavailability is 92% (in healthy volunteers).
- Volume of distribution
- 0.38 liters/kg [intravenous injections of 12.5 mcg/kg to 125 mcg/kg to congestive heart failure patients]
- 0.45 liters/kg [intravenous infusions of 0.20 mcg/kg/min to 0.70 mcg/kg/min to congestive heart failure patients]
- Protein binding
70 to 80%
- Metabolism
There are five metabolites but the O-glucuronide represents the major pathway of biotransformation.
- Route of elimination
The primary route of excretion of milrinone in man is via the urine.
- Half-life
2.3 hours
- Clearance
- 0.13 L/kg/hr [congestive heart failure patients, following IV injections of 12.5 mcg/kg to 125 mcg/kg]
- 0.14 L/kg/hr [congestive heart failure patients, following infusions of 0.2 mcg/kg/min to 0.7 mcg/kg/min]
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
LD50 = 0.3 mg/L in rats
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbacavir Milrinone may decrease the excretion rate of Abacavir which could result in a higher serum level. Acarbose Milrinone may decrease the excretion rate of Acarbose which could result in a higher serum level. Acebutolol Milrinone may increase the antihypertensive activities of Acebutolol. Aceclofenac Aceclofenac may decrease the excretion rate of Milrinone which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Milrinone which could result in a higher serum level. Acetaminophen Milrinone may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Milrinone which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Milrinone which could result in a higher serum level. Aclidinium Milrinone may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Milrinone may decrease the excretion rate of Acrivastine which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Milrinone lactate 9K8XR81MO8 100286-97-3 VWUPWEAFIOQCGF-UHFFFAOYSA-N - International/Other Brands
- Corotrop / Corotrope / Milrila
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataMilrinone Injection Solution Intravenous TEVA Canada Limited 2003-05-25 2015-07-22 Canada 
Milrinone Lactate Injection, solution 1 mg/1mL Intravenous Hospira, Inc. 2006-07-17 2006-07-17 US 
Milrinone Lactate in Dextrose Injection 200 ug/1mL Intravenous Baxter Healthcare Corporation 2006-07-27 2006-07-27 US Milrinone Lactate Injection Solution Intravenous Sandoz Canada Incorporated 2003-06-25 Not applicable Canada Milrinone Lactate Injection Solution Intravenous Sterimax Inc Not applicable Not applicable Canada Milrinone Lactate Injection Solution Intravenous Auro Pharma Inc 2018-12-24 Not applicable Canada Milrinone Lactate Injection Solution Intravenous Strides Pharma Canada Inc Not applicable Not applicable Canada Milrinone Lactate Injection, USP Solution Intravenous Fresenius Kabi 2003-07-03 Not applicable Canada Primacor Injection, solution 200 ug/1mL Intravenous sanofi-aventis U.S. LLC 1987-12-31 2009-09-30 US Primacor Injection, solution 1 mg/1mL Intravenous Sanofi-Synthelabo Inc. 2006-05-10 2018-10-11 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataApo-milrinone Injectable Solution Intravenous Apotex Corporation 2005-07-29 2013-08-02 Canada Milrinone Lactate Injection 1 mg/1mL Intravenous Gland Pharma Limited 2017-07-28 Not applicable US Milrinone Lactate Injection 1 mg/1mL Intravenous Bedford Pharmaceuticals 2002-05-27 2012-02-29 US Milrinone Lactate Injection, solution 1 mg/1mL Intravenous Meitheal Pharmaceuticals Inc. 2020-03-24 Not applicable US Milrinone Lactate Injection, solution 200 ug/1mL Intravenous Hikma Farmaceutica 2010-01-21 2010-01-21 US Milrinone lactate Injection, solution 1 mg/1mL Intravenous Apotex Corporation 2004-09-21 2010-07-01 US Milrinone Lactate Injection, solution 1 mg/1mL Intravenous West-Ward Pharmaceuticals Corp 2010-12-03 Not applicable US Milrinone Lactate Injection, solution 0.2 mg/1mL Intravenous AuroMedics Pharma LLC 2020-09-03 Not applicable US Milrinone Lactate Injection 1 mg/1mL Intravenous West Ward Pharmaceutical 2002-05-28 Not applicable US Milrinone Lactate Injection 1 mg/1mL Intravenous Bedford Pharmaceuticals 2002-05-27 2015-05-31 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Milrinone Lactate in Dextrose Milrinone lactate (200 ug/1mL) + D-glucose monohydrate (49.4 mg/1mL) Injection Intravenous B. Braun Medical Inc. 2007-10-29 Not applicable US
Categories
- ATC Codes
- C01CE02 — Milrinone
- Drug Categories
- Amines
- Aminopyridines
- Cardiac Stimulants Excl. Cardiac Glycosides
- Cardiac Therapy
- Cardiotonic Agents
- Cardiovascular Agents
- Compounds used in a research, industrial, or household setting
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Hematologic Agents
- Phosphodiesterase 3 Inhibitors
- Phosphodiesterase 5 Inhibitors
- Phosphodiesterase Inhibitors
- Protective Agents
- Pyridines
- Vasodilating Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Bipyridines and oligopyridines
- Direct Parent
- Bipyridines and oligopyridines
- Alternative Parents
- 3-pyridinecarbonitriles / Methylpyridines / Hydroxypyridines / Heteroaromatic compounds / Nitriles / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Hydrocarbon derivatives
- Substituents
- 3-pyridinecarbonitrile / Aromatic heteromonocyclic compound / Azacycle / Bipyridine / Carbonitrile / Heteroaromatic compound / Hydrocarbon derivative / Hydroxypyridine / Methylpyridine / Nitrile
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- nitrile, pyridone, bipyridines (CHEBI:50693)
Chemical Identifiers
- UNII
- JU9YAX04C7
- CAS number
- 78415-72-2
- InChI Key
- PZRHRDRVRGEVNW-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 6-methyl-2-oxo-5-(pyridin-4-yl)-1,2-dihydropyridine-3-carbonitrile
- SMILES
- CC1=C(C=C(C#N)C(=O)N1)C1=CC=NC=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014380
- KEGG Drug
- D00417
- KEGG Compound
- C07224
- PubChem Compound
- 4197
- PubChem Substance
- 46507838
- ChemSpider
- 4052
- BindingDB
- 15296
- 52769
- ChEBI
- 50693
- ChEMBL
- CHEMBL189
- ZINC
- ZINC000009224016
- Therapeutic Targets Database
- DAP000150
- PharmGKB
- PA164749171
- PDBe Ligand
- MIL
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Milrinone
- AHFS Codes
- 24:04.08 — Cardiotonic Agents
- PDB Entries
- 1tlm
- FDA label
- Download (491 KB)
- MSDS
- Download (34.8 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Acute Coronary Syndromes (ACS) / Low Cardiac Output Syndrome / Pulmonary Edemas / Shock, Cardiogenic 1 4 Not Yet Recruiting Supportive Care Pulmonary Hypertension Due to Left Heart Disease 1 4 Recruiting Treatment Cardiomyopathy / Shock, Septic 1 4 Recruiting Treatment Hemodynamics 1 3 Completed Treatment Cardiac Output, Low 1 3 Completed Treatment Mitral Valve Insufficiency / Pulmonary Hypertension (PH) 1 3 Not Yet Recruiting Treatment Vasospasm 1 3 Recruiting Treatment Cardiac Surgical Procedures / Infants / Low Cardiac Output Syndrome 1 2 Completed Prevention Defect, Congenital Heart 1 2 Completed Prevention Pulmonary Hypertension (PH) 1
Pharmacoeconomics
- Manufacturers
- App pharmaceuticals llc
- Baxter healthcare corp anesthesia and critical care
- Baxter healthcare corp anesthesia critical care
- Bedford laboratories div ben venue laboratories inc
- Bioniche pharma usa llc
- Claris lifesciences ltd
- Gland pharma ltd
- Hospira inc
- International medicated systems ltd
- B braun medical inc
- Baxter healthcare corp
- Bedford laboratories
- Hikma farmaceutica (portugal) sa
- Sanofi aventis us llc
- Packagers
- Alchymars SPA
- Apotex Inc.
- APP Pharmaceuticals
- B. Braun Melsungen AG
- Baxter International Inc.
- Bedford Labs
- Ben Venue Laboratories Inc.
- Bioniche Pharma
- Cardinal Health
- Hospira Inc.
- Sanofi-Aventis Inc.
- Teva Pharmaceutical Industries Ltd.
- Dosage Forms
Form Route Strength Solution Intravenous 10 mg/10ml Injection, solution Intravenous 1 mg/ml Solution Intravenous 20 mg Solution Intravenous 0.01 g Solution Intravenous 1 mg Injection Intravenous 1 mg/1mL Injection Intravenous 20 mg/100mL Injection, solution Intravenous 200 ug/1mL Injection Intravenous Injection Intravenous 200 ug/1mL Injection, solution Intravenous 0.2 mg/1mL Solution Intravenous 10 mg Injection, solution Intravenous 1 mg/1mL Injection Solution Intravenous - Prices
Unit description Cost Unit Primacor 0.2 mg/ml-d5w 100 ml 1.6USD ml Milrinone-d5w 20 mg/100 ml 1.45USD ml Milrinone lact 20 mg/20 ml vial 1.44USD ml Milrinone lact 10 mg/10 ml vial 1.31USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) >300 °C PhysProp water solubility Slightly soluble Not Available logP 0.4 Not Available - Predicted Properties
Property Value Source Water Solubility 0.209 mg/mL ALOGPS logP 1.04 ALOGPS logP 0.33 ChemAxon logS -3 ALOGPS pKa (Strongest Acidic) 7.54 ChemAxon pKa (Strongest Basic) 4.82 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 65.78 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 61.14 m3·mol-1 ChemAxon Polarizability 21.46 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9807 Caco-2 permeable + 0.6889 P-glycoprotein substrate Non-substrate 0.8041 P-glycoprotein inhibitor I Non-inhibitor 0.7835 P-glycoprotein inhibitor II Non-inhibitor 0.9799 Renal organic cation transporter Non-inhibitor 0.8614 CYP450 2C9 substrate Non-substrate 0.7016 CYP450 2D6 substrate Non-substrate 0.8411 CYP450 3A4 substrate Non-substrate 0.5641 CYP450 1A2 substrate Inhibitor 0.5399 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9816 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8827 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7866 Ames test Non AMES toxic 0.7822 Carcinogenicity Non-carcinogens 0.9351 Biodegradation Not ready biodegradable 0.993 Rat acute toxicity 2.5820 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.991 hERG inhibition (predictor II) Non-inhibitor 0.8941
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes.
- Gene Name
- PDE3A
- Uniprot ID
- Q14432
- Uniprot Name
- cGMP-inhibited 3',5'-cyclic phosphodiesterase A
- Molecular Weight
- 124978.06 Da
References
- Cone J, Wang S, Tandon N, Fong M, Sun B, Sakurai K, Yoshitake M, Kambayashi J, Liu Y: Comparison of the effects of cilostazol and milrinone on intracellular cAMP levels and cellular function in platelets and cardiac cells. J Cardiovasc Pharmacol. 1999 Oct;34(4):497-504. [PubMed:10511123]
- Kuthe A, Magert H, Uckert S, Forssmann WG, Stief CG, Jonas U: Gene expression of the phosphodiesterases 3A and 5A in human corpus cavernosum penis. Eur Urol. 2000 Jul;38(1):108-14. [PubMed:10859452]
- Lefievre L, de Lamirande E, Gagnon C: Presence of cyclic nucleotide phosphodiesterases PDE1A, existing as a stable complex with calmodulin, and PDE3A in human spermatozoa. Biol Reprod. 2002 Aug;67(2):423-30. [PubMed:12135876]
- Zhang W, Ke H, Colman RW: Identification of interaction sites of cyclic nucleotide phosphodiesterase type 3A with milrinone and cilostazol using molecular modeling and site-directed mutagenesis. Mol Pharmacol. 2002 Sep;62(3):514-20. [PubMed:12181427]
- Shakur Y, Fong M, Hensley J, Cone J, Movsesian MA, Kambayashi J, Yoshitake M, Liu Y: Comparison of the effects of cilostazol and milrinone on cAMP-PDE activity, intracellular cAMP and calcium in the heart. Cardiovasc Drugs Ther. 2002 Sep;16(5):417-27. [PubMed:12652111]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Drug created on June 13, 2005 07:24 / Updated on September 24, 2020 02:08
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