U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H9N3O
Molecular Weight 211.2194
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MILRINONE

SMILES

CC1=C(C=C(C#N)C(=O)N1)C2=CC=NC=C2

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

Molecular Formula C12H9N3O
Molecular Weight 211.2194
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

2002
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
Vascular relaxant effects of toborinone on the isolated canine internal mammary artery.
2001
High calcium and dobutamine positive inotropy in the perfused mouse heart: myofilament calcium responsiveness, energetic economy, and effects of protein kinase C inhibition.
2001
Possible involvement of cyclic adenosine monophosphate-independent mechanism in the positive chronotropic effect of norepinephrine in the isolated guinea pig right atrium.
2001 Aug
A conscious-rabbit model to study vardenafil hydrochloride and other agents that influence penile erection.
2001 Aug
Cardioprotective effect afforded by transient exposure to phosphodiesterase III inhibitors: the role of protein kinase A and p38 mitogen-activated protein kinase.
2001 Aug 7
Identification and functional study of phosphodiesterases in rat urinary bladder.
2001 Dec
[The pulmonary vasodilatory effect of inhaled prostacyclin and milrinone in heart].
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
Milrinone echocardiographic viability test: a pilot study.
2001 Jul
The effects of alpha-human atrial natriuretic peptide and milrinone on pial vessels during blood-brain barrier disruption in rabbits.
2001 Jul
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
Interplay between inhibition of adenosine uptake and phosphodiesterase type 3 on cardiac function by cilostazol, an agent to treat intermittent claudication.
2001 Nov
Cell-based assay for high-throughput quantitative screening of CFTR chloride transport agonists.
2001 Nov
The evolving management of acute right-sided heart failure in cardiac transplant recipients.
2001 Oct
Effects of milrinone on left ventricular end-systolic pressure-volume relationship of rat hearts in situ.
2001 Sep
Assessment of cardiovascular dynamics by pressure-area relations in pediatric patients with congenital heart disease.
2001 Sep
Carvedilol titration in patients with congestive heart failure receiving inotropic therapy.
2001 Sep
Nitric oxide-cGMP pathway facilitates acetylcholine release and bradycardia during vagal nerve stimulation in the guinea-pig in vitro.
2001 Sep 1
Cilostazol (pletal): a dual inhibitor of cyclic nucleotide phosphodiesterase type 3 and adenosine uptake.
2001 Winter
Differential effects of specific phosphodiesterase isoenzyme inhibitors on bovine oocyte meiotic maturation.
2002 Apr 15
Presence of cyclic nucleotide phosphodiesterases PDE1A, existing as a stable complex with calmodulin, and PDE3A in human spermatozoa.
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
Involvement of phosphodiesterase isozymes in osteoblastic differentiation.
2002 Feb
Intravenous milrinone in cardiac surgery.
2002 Jan
Effects of milrinone for right ventricular failure after left ventricular assist device implantation.
2002 Jan
Assessing the emetic potential of PDE4 inhibitors in rats.
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
Activation of protein kinase A by nitric oxide in cultured dorsal root ganglion neurites of the rat, examined by a fluorescence probe, ARII.
2002 Jan 18
Mechanisms of leptin secretion from white adipocytes.
2002 Jul
Levosimendan: a unique approach to the treatment of heart failure.
2002 Jul-Aug
22nd International Symposium on Intensive Care and Emergency Medicine, Brussels, Belgium, 19-22 March 2002.
2002 Jun
Recently published papers: topical issues in pharmacology.
2002 Jun
Effects of milrinone on hemodynamics and regional blood flow in the hypoxic dog.
2002 Jun
Cardiac performance during vasopressin infusion in postcardiotomy shock.
2002 Jun
Physical compatibility of milrinone lactate injection with intravenous drugs commonly used in the pediatric intensive care unit.
2002 Mar 1
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
A potential role for AMP-activated protein kinase in meiotic induction in mouse oocytes.
2002 May 1
Effects of cAMP modulators on long-chain fatty-acid uptake and utilization by electrically stimulated rat cardiac myocytes.
2002 Nov 1
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
Exhaled nitric oxide: a marker of pulmonary hemodynamics in heart failure.
2002 Sep 18
Subtype-specific roles of cAMP phosphodiesterases in regulation of atrial natriuretic peptide release.
2002 Sep 20
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:11:59 GMT 2023
Edited
by admin
on Fri Dec 15 16:11:59 GMT 2023
Record UNII
JU9YAX04C7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MILRINONE
INN   JAN   MART.   MI   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
Milrinone [WHO-DD]
Common 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 [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 Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
FDA ORPHAN DRUG 565916
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
WHO-ATC C01CE02
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
NDF-RT N0000175086
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
WHO-VATC QC01CE02
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
NCI_THESAURUS C744
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
Code System Code Type Description
MESH
D020105
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
ECHA (EC/EINECS)
278-903-6
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
SMS_ID
100000080655
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID5023324
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
NCI_THESAURUS
C61848
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
RS_ITEM_NUM
1443908
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
ChEMBL
CHEMBL189
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
USAN
T-72
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
WIKIPEDIA
MILRINONE
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
INN
5383
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
DAILYMED
JU9YAX04C7
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
CAS
78415-72-2
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
MERCK INDEX
m7548
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
1809
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
CHEBI
50693
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
RXCUI
52769
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY RxNorm
NSC
760072
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
DRUG BANK
DB00235
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
EVMPD
SUB08968MIG
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
IUPHAR
5225
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
FDA UNII
JU9YAX04C7
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
PUBCHEM
4197
Created by admin on Fri Dec 15 16:11:59 GMT 2023 , Edited by admin on Fri Dec 15 16:11:59 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
IC50
Related Record Type Details
METABOLITE -> PARENT
MAJOR
URINE
Related Record Type Details
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC Normal renal function
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC Severe heart failure with (CVVH)continuous venovenous hemfiltration.
PHARMACOKINETIC