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Details

Stereochemistry ACHIRAL
Molecular Formula C12H9N3O
Molecular Weight 211.2198
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MILRINONE

SMILES

Cc1c(cc(C#N)c(n1)O)-c2ccncc2

InChI

InChIKey=PZRHRDRVRGEVNW-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/cdi/milrinone.html

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. 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. Milrinone is indicated for the treatment of congestive heart failure. Milrinone was marketed under the brand name Primacor.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.45 µM [IC50]
1.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Milrinone Lactate

Approved Use

Milrinone lactate injection is indicated for the short-term intravenous treatment of patients with acute decompensated heart failure.

Launch Date

1.02245761E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
162 μg/L
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MILRINONE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
454 μg/L
75 μg/kg bw single, intravenous
dose: 75 μg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MILRINONE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1.749 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MILRINONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
439 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MILRINONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.92 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MILRINONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.758 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MILRINONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.94 h
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
MILRINONE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
1.7 h
75 μg/kg bw single, intravenous
dose: 75 μg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MILRINONE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Milrinone for the treatment of cerebral vasospasm after subarachnoid hemorrhage: report of seven cases.
2001 Apr
Identification and functional study of phosphodiesterases in rat urinary bladder.
2001 Dec
Comparison of milrinone versus nitroglycerin, alone and in combination, on grafted internal mammary artery flow after cardiopulmonary bypass: effects of alpha-adrenergic stimulation.
2001 Dec
Milrinone versus dobutamine in heart failure subjects treated chronically with carvedilol.
2001 Dec
Inhibition of cyclic-3',5'-nucleotide phosphodiesterase abrogates the synergism of hypoxia with lipopolysaccharide in the induction of macrophage TNF-alpha production.
2001 Dec
The additive pulmonary vasodilatory effects of inhaled prostacyclin and inhaled milrinone in postcardiac surgical patients with pulmonary hypertension.
2001 Dec
Comparison of dobutamine-based and milrinone-based therapy for advanced decompensated congestive heart failure: Hemodynamic efficacy, clinical outcome, and economic impact.
2001 Dec
Natriuretic peptides like NO facilitate cardiac vagal neurotransmission and bradycardia via a cGMP pathway.
2001 Dec
Slow induction of milrinone after coronary artery bypass grafting.
2001 Feb
[Effect of colforsin daropate hydrochloride after cardiopulmonary bypass].
2001 Jan
Iloprost inhibits inositol-1,4,5-trisphosphate-mediated calcium mobilization stimulated by angiotensin II in cultured preglomerular vascular smooth muscle cells.
2001 Jan
"cAMP-specific" phosphodiesterase contributes to cGMP degradation in cerebellar cells exposed to nitric oxide.
2001 Jan
Surgical issues in heart failure: what's new?
2001 Jun
Inotropes and beta-blockers: is there a need for new guidelines?
2001 Jun
Dose response to nitric oxide in adult cardiac surgery patients.
2001 Jun
Comparison of the hemodynamic effects of milrinone with dobutamine in patients after cardiac surgery.
2001 Jun
Modulation of thapsigargin-induced calcium mobilisation by cyclic AMP-elevating agents in human lymphocytes is insensitive to the action of the protein kinase A inhibitor H-89.
2001 Jun
Combined phosphodiesterase inhibition and beta-blockade in the GI104313, decreases ischemia-induced arrhythmias in the rat.
2001 May
Sildenafil (viagra) facilitates weaning of inhaled nitric oxide following placement of a biventricular-assist device.
2001 May
Inhibitory effects of cyclic AMP elevating agents on lipopolysaccharide (LPS)-induced microvascular permeability change in mouse skin.
2001 May
Discriminative stimulus effects of the type-4 phosphodiesterase inhibitor rolipram in rats.
2001 Nov
Cell-based assay for high-throughput quantitative screening of CFTR chloride transport agonists.
2001 Nov
Synergistic interaction of diazepam with 3',5'-cyclic adenosine monophosphate-elevating agents on rat aortic rings.
2001 Oct 5
Cilostazol (pletal): a dual inhibitor of cyclic nucleotide phosphodiesterase type 3 and adenosine uptake.
2001 Winter
Modulation of TNF and GM-CSF release from dispersed human nasal polyp cells and human whole blood by inhibitors of different PDE isoenzymes and glucocorticoids.
2002
Positive inotropic drug infusions for patients with heart failure: current controversies and best practice.
2002 Apr
Differential effects of specific phosphodiesterase isoenzyme inhibitors on bovine oocyte meiotic maturation.
2002 Apr 15
The effectiveness and relative effectiveness of intravenous inotropic drugs acting through the adrenergic pathway in patients with heart failure-a meta-regression analysis.
2002 Aug
Phosphodiesterase 3 inhibitors selectively block the spontaneous resumption of meiosis by macaque oocytes in vitro.
2002 Aug
[Reversible cardiomyopathy secondary to interferon-alpha in chronic myelogenous leukemia].
2002 Feb
Milrinone increases middle cerebral artery blood flow velocity after cardiopulmonary bypass.
2002 Feb
Intravenous milrinone in cardiac surgery.
2002 Jan
Effects of milrinone for right ventricular failure after left ventricular assist device implantation.
2002 Jan
The efficacy of preemptive Milrinone or Amrinone therapy in patients undergoing coronary artery bypass grafting.
2002 Jan
Effect of type 3 and type 4 phosphodiesterase inhibitors on the maintenance of bovine oocytes in meiotic arrest.
2002 Jan
Cyclic AMP-dependent Cl secretion is regulated by multiple phosphodiesterase subtypes in human colonic epithelial cells.
2002 Jan 15
[Pharmacology of inotropic agents].
2002 Jan-Mar
Mechanisms of leptin secretion from white adipocytes.
2002 Jul
Levosimendan: a unique approach to the treatment of heart failure.
2002 Jul-Aug
Effects of phosphodiesterase III inhibition on length-dependent regulation of myocardial function in coronary surgery patients.
2002 Jun
Effects of milrinone on hemodynamics and regional blood flow in the hypoxic dog.
2002 Jun
Treatment of acute heart failure: out with the old, in with the new.
2002 Mar 27
Short-term intravenous milrinone for acute exacerbation of chronic heart failure: a randomized controlled trial.
2002 Mar 27
Differential regulation of human platelet responses by cGMP inhibited and stimulated cAMP phosphodiesterases.
2002 May
Novel use of a short-acting intravenous beta blocker in combination with inotropic therapy as a bridge to chronic oral beta blockade in patients with advanced heart failure.
2002 May
A potential role for AMP-activated protein kinase in meiotic induction in mouse oocytes.
2002 May 1
Control of renin secretion from rat juxtaglomerular cells by cAMP-specific phosphodiesterases.
2002 May 17
New mechanism of action for cilostazol: interplay between adenosine and cilostazol in inhibiting platelet activation.
2002 Oct
Lipopolysaccharide-induced acute renal failure in conscious rats: effects of specific phosphodiesterase type 3 and 4 inhibition.
2002 Oct
Identification of interaction sites of cyclic nucleotide phosphodiesterase type 3A with milrinone and cilostazol using molecular modeling and site-directed mutagenesis.
2002 Sep
Patents

Patents

Sample Use Guides

Usual Adult Dose for Congestive Heart Failure Loading dose: 50 mcg/kg IV over 10 minutes. Maintenance infusion: 0.375 to 0.75 mcg/kg/min.
Route of Administration: Intravenous
Milrinone caused the human thoracic artery samples to relax at 10⁻⁴ M concentrations by 44%, when the external Ca²⁺ corresponded to the physiological standard.
Name Type Language
MILRINONE
INN   JAN   MART.   MI   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
MILRILA
Brand Name English
MILRINONE [USP-RS]
Common Name English
WIN 47,203-2
Code English
MILRINONE [USAN]
Common Name English
MILRINONE [JAN]
Common Name English
WIN-47203-2
Code English
MILRINONE [USP MONOGRAPH]
Common Name English
MILRINONE [MI]
Common Name English
MILRINONE [INN]
Common Name English
MILRINONE [WHO-DD]
Common Name English
MILRINONE [VANDF]
Common Name English
NSC-760072
Code English
MILRINONE [MART.]
Common Name English
(3,4'-BIPYRIDINE)-5-CARBONITRILE, 1,6-DIHYDRO-2-METHYL-6-OXO-
Systematic Name English
1,6-DIHYDRO-2-METHYL-6-OXO(3,4'-BIPYRIDINE)-5-CARBONITRILE
Systematic Name English
Classification Tree Code System Code
NDF-RT N0000175598
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
FDA ORPHAN DRUG 565916
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
WHO-ATC C01CE02
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
NDF-RT N0000175086
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
WHO-VATC QC01CE02
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
NCI_THESAURUS C744
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
Code System Code Type Description
MESH
D020105
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY
ECHA (EC/EINECS)
278-903-6
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY
EPA CompTox
78415-72-2
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY
NCI_THESAURUS
C61848
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY
ChEMBL
CHEMBL189
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY
WIKIPEDIA
MILRINONE
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY
INN
5383
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY
CAS
78415-72-2
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY
MERCK INDEX
M7548
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
1809
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY
RXCUI
52769
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00235
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY
USP_CATALOG
1443908
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY USP-RS
EVMPD
SUB08968MIG
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY
IUPHAR
5225
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY
FDA UNII
JU9YAX04C7
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY
PUBCHEM
4197
Created by admin on Fri Jun 25 21:03:41 UTC 2021 , Edited by admin on Fri Jun 25 21:03:41 UTC 2021
PRIMARY