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

Details

Stereochemistry ACHIRAL
Molecular Formula C10H9N3O
Molecular Weight 187.1983
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INAMRINONE

SMILES

c1cnccc1-c2cc(c(nc2)O)N

InChI

InChIKey=RNLQIBCLLYYYFJ-UHFFFAOYSA-N
InChI=1S/C10H9N3O/c11-9-5-8(6-13-10(9)14)7-1-3-12-4-2-7/h1-6H,11H2,(H,13,14)

HIDE SMILES / InChI

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

Inamrinone (Amrinone) is a positive inotropic cardiotonic with vasodilator properties, phosphodiesterase inhibitory activity, and the ability to stimulate calcium ion influx into the cardiac cell. Inamrinone is a phosphodiesterase inhibitor (PDE3), resulting in increased cAMP and cGMP which leads to an increase in the calcium influx like that caused by beta-agonists resulting in increased inotropic effect. Inamrinone is used in the treatment of congestive heart failure.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
16.7 µM [IC50]
31.2 µM [IC50]
61.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AMRINONE LACTATE

Approved Use

For the short-term management of congestive heart failure.

Launch Date

9.5774402E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.2 μg/mL
0.75 mg/kg 3 times / day steady-state, intravenous
dose: 0.75 mg/kg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
INAMRINONE plasma
Homo sapiens
population: UNKNOWN
age: NEWBORN
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
245 μg × h/mL
0.75 mg/kg 3 times / day steady-state, intravenous
dose: 0.75 mg/kg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
INAMRINONE plasma
Homo sapiens
population: UNKNOWN
age: NEWBORN
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.4 h
0.75 mg/kg 3 times / day steady-state, intravenous
dose: 0.75 mg/kg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
INAMRINONE plasma
Homo sapiens
population: UNKNOWN
age: NEWBORN
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
198 ug/kg/min 1 times / day single, intravenous (max)
Overdose
Dose: 198 ug/kg/min, 1 times / day
Route: intravenous
Route: single
Dose: 198 ug/kg/min, 1 times / day
Sources:
unhealthy, 0.208333333333333
n = 1
Health Status: unhealthy
Condition: heart failure
Age Group: 0.208333333333333
Sex: F
Population Size: 1
Sources:
Other AEs: Cardiac arrest...
198 ug/kg/min 1 times / day single, intravenous (max)
Overdose
Dose: 198 ug/kg/min, 1 times / day
Route: intravenous
Route: single
Dose: 198 ug/kg/min, 1 times / day
Sources:
unhealthy, 0.208333333333333
n = 1
Health Status: unhealthy
Condition: heart failure
Age Group: 0.208333333333333
Sex: F
Population Size: 1
Sources:
Other AEs: Death...
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 49
n = 13
Health Status: unhealthy
Condition: congestive heart failure
Age Group: 49
Sex: M+F
Population Size: 13
Sources:
Disc. AE: Pulmonary edema, Cardiac arrest...
AEs leading to
discontinuation/dose reduction:
Pulmonary edema
Cardiac arrest
Respiratory distress syndrome
Chest pain
Palpitations
Ventricular ectopic beats
Sources:
200 mg 3 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
unhealthy, 53
n = 32
Health Status: unhealthy
Condition: congestive heart failure
Age Group: 53
Sex: M+F
Population Size: 32
Sources:
Disc. AE: Diarrhea, Thrombocytopenia...
AEs leading to
discontinuation/dose reduction:
Diarrhea
Thrombocytopenia
Sources:
5.8 mg/kg/day 1 times / day multiple, intravenous (mean)
Recommended
Dose: 5.8 mg/kg/day, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.8 mg/kg/day, 1 times / day
Sources:
unhealthy, 59.4 (37-81)
n = 43
Health Status: unhealthy
Condition: congestive heart failure
Age Group: 59.4 (37-81)
Sex: M+F
Population Size: 43
Sources:
Disc. AE: Thrombocytopenia...
AEs leading to
discontinuation/dose reduction:
Thrombocytopenia (18.6%)
Sources:
3 mg/kg 1 times / day single, intravenous (max)
Recommended
Dose: 3 mg/kg, 1 times / day
Route: intravenous
Route: single
Dose: 3 mg/kg, 1 times / day
Sources:
unhealthy, <1
n = 6
Health Status: unhealthy
Condition: pulmonary hypertension
Age Group: <1
Sex: M+F
Population Size: 6
Sources:
AEs

AEs

AESignificanceDosePopulation
Cardiac arrest
198 ug/kg/min 1 times / day single, intravenous (max)
Overdose
Dose: 198 ug/kg/min, 1 times / day
Route: intravenous
Route: single
Dose: 198 ug/kg/min, 1 times / day
Sources:
unhealthy, 0.208333333333333
n = 1
Health Status: unhealthy
Condition: heart failure
Age Group: 0.208333333333333
Sex: F
Population Size: 1
Sources:
Death grade 5
198 ug/kg/min 1 times / day single, intravenous (max)
Overdose
Dose: 198 ug/kg/min, 1 times / day
Route: intravenous
Route: single
Dose: 198 ug/kg/min, 1 times / day
Sources:
unhealthy, 0.208333333333333
n = 1
Health Status: unhealthy
Condition: heart failure
Age Group: 0.208333333333333
Sex: F
Population Size: 1
Sources:
Cardiac arrest Disc. AE
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 49
n = 13
Health Status: unhealthy
Condition: congestive heart failure
Age Group: 49
Sex: M+F
Population Size: 13
Sources:
Chest pain Disc. AE
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 49
n = 13
Health Status: unhealthy
Condition: congestive heart failure
Age Group: 49
Sex: M+F
Population Size: 13
Sources:
Palpitations Disc. AE
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 49
n = 13
Health Status: unhealthy
Condition: congestive heart failure
Age Group: 49
Sex: M+F
Population Size: 13
Sources:
Pulmonary edema Disc. AE
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 49
n = 13
Health Status: unhealthy
Condition: congestive heart failure
Age Group: 49
Sex: M+F
Population Size: 13
Sources:
Respiratory distress syndrome Disc. AE
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 49
n = 13
Health Status: unhealthy
Condition: congestive heart failure
Age Group: 49
Sex: M+F
Population Size: 13
Sources:
Ventricular ectopic beats Disc. AE
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 49
n = 13
Health Status: unhealthy
Condition: congestive heart failure
Age Group: 49
Sex: M+F
Population Size: 13
Sources:
Diarrhea Disc. AE
200 mg 3 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
unhealthy, 53
n = 32
Health Status: unhealthy
Condition: congestive heart failure
Age Group: 53
Sex: M+F
Population Size: 32
Sources:
Thrombocytopenia Disc. AE
200 mg 3 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
unhealthy, 53
n = 32
Health Status: unhealthy
Condition: congestive heart failure
Age Group: 53
Sex: M+F
Population Size: 32
Sources:
Thrombocytopenia 18.6%
Disc. AE
5.8 mg/kg/day 1 times / day multiple, intravenous (mean)
Recommended
Dose: 5.8 mg/kg/day, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.8 mg/kg/day, 1 times / day
Sources:
unhealthy, 59.4 (37-81)
n = 43
Health Status: unhealthy
Condition: congestive heart failure
Age Group: 59.4 (37-81)
Sex: M+F
Population Size: 43
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Amrinone for refractory cardiogenic shock following chloroquine poisoning.
1991
Congenital junctional ectopic tachycardia: presentation and outcome.
2003 Jul 1
Effects of dopamine, dobutamine, amrinone and milrinone on regional blood flow in isoflurane anesthetized dogs.
2004 Sep
Successful allogeneic bone marrow transplantation for acute myelogenous leukemia after drug-induced cardiomyopathy.
2004 Sep
Meta-analysis of hemodynamic optimization: relationship to methodological quality.
2005
Effects of a phosphodiesterase 3 inhibitor, olprinone, on rhythmical change in tension of human gastroepiploic artery.
2005 Dec 28
SCH00013, a novel Ca(2+) sensitizer with positive inotropic and no chronotropic action in heart failure.
2005 Jan
Effect of amrinone on mucosal permeability in experimental intestinal ischaemia/reperfusion injury.
2005 Jul
The impact of slow rewarming on inotropy, tissue metabolism, and "after drop" of body temperature in pediatric patients.
2005 Jun
Bench-to-bedside review: Inotropic drug therapy after adult cardiac surgery -- a systematic literature review.
2005 Jun
A sensitive and specific high performance liquid chromatographic assay for milrinone in rat and human plasma using a commercially available internal standard and low sample volume.
2005 Jun 24
Protective effects of different antioxidants and amrinone on vancomycin-induced nephrotoxicity.
2005 Nov
Effects of inotropic drugs on mechanical function and oxygen balance in postischemic canine myocardium: comparison of dobutamine, epinephrine, amrinone, and calcium chloride.
2005 Oct
Differential pharmacologic sensitivities of phosphodiesterase-3 inhibitors among human isolated gastroepiploic, internal mammary, and radial arteries.
2005 Oct
Bench-to-bedside review: thrombocytopenia-associated multiple organ failure--a newly appreciated syndrome in the critically ill.
2006
Bench-to-bedside review: hyperinsulinaemia/euglycaemia therapy in the management of overdose of calcium-channel blockers.
2006
In vivo dilatation of the fetal and postnatal ductus arteriosus by inhibition of phosphodiesterase 3 in rats.
2006
The effect of amrinone on liver regeneration in experimental hepatic resection model.
2006 Jan
Alkaline Phosphatases : Structure, substrate specificity and functional relatedness to other members of a large superfamily of enzymes.
2006 Jun
Effect of combining phosphodiesterase III inhibitors with St Thomas Hospital's solution used as transplantation preservative solution in isolated rat hearts.
2006 Jun
A comparison of three phosphodiesterase type III inhibitors on mechanical and metabolic function in guinea pig isolated hearts.
2006 Jun
Contractile responses to selective phosphodiesterase inhibitors following chronic beta-adrenoreceptor activation.
2006 May
Acute heart failure: inotropic agents and their clinical uses.
2006 Nov
Coronary bypass grafting using crossclamp fibrillation does not result in reliable reperfusion of the myocardium when the crossclamp is intermittently released: a prospective cohort study.
2006 Nov 21
Treatment of poisoning caused by beta-adrenergic and calcium-channel blockers.
2006 Oct 1
Proper use of phosphodiesterase inhibitors according to the situations.
2006 Sep
[Current approaches to intraoperative diagnosis and treatment of low cardiac output during cardiosurgical operations].
2006 Sep-Oct
Investigation of binding proteins for anti-platelet agent K-134 by Drug-Western method.
2007 Feb 23
Effects of phosphodiesterase (PDE) inhibitors on human ether-a-go-go related gene (hERG) channel activity.
2007 Jan-Feb
[Protection of amrinone against lung injury induced by ischemia/reperfusion in rats].
2007 Jun
Cirrhotic cardiomyopathy.
2007 Mar 27
Peripartum cardiomyopathy: review of the literature.
2007 Oct 31
Inotropic and chronotropic effects of 6-hydroxy-4-methylquinolin-2(1H)-one derivatives in isolated rat atria.
2008 Apr
Tadalafil in the treatment of erectile dysfunction.
2008 Dec
Surviving Sepsis Campaign: international guidelines for management of severe sepsis and septic shock: 2008.
2008 Jan
Comparison of the initial hospitalization costs between the patients treated with dobutamine and the patients treated with amrinone for acute decompensated heart failure in a Japanese institute.
2008 Mar
Labetalol infusion for refractory hypertension causing severe hypotension and bradycardia: an issue of patient safety.
2008 May 27
The base exchange reaction of NAD+ glycohydrolase: identification of novel heterocyclic alternative substrates.
2008 Nov 15
Vesnarinone represses the fibrotic changes in murine lung injury induced by bleomycin.
2009
Effect of nitric oxide/cyclic guanosine mono-phosphate pathway on gallbladder relaxant response in bile duct-ligated guinea pigs.
2009
Design, synthesis and pharmacological evaluation of 6-hydroxy-4-methylquinolin-2(1H)-one derivatives as inotropic agents.
2009 Aug
Drug effect unveils inter-head cooperativity and strain-dependent ADP release in fast skeletal actomyosin.
2009 Aug 21
Effects of propofol on responses of rat isolated renal arteriole to vasoactive agents.
2009 Aug-Sep
Agents with inotropic properties for the management of acute heart failure syndromes. Traditional agents and beyond.
2009 Dec
Gene expression analysis reveals new possible mechanisms of vancomycin-induced nephrotoxicity and identifies gene markers candidates.
2009 Jan
Effects of amrinone in an experimental model of hepatic ischemia-reperfusion injury.
2009 Jan
Evaluation of preoperative intra-aortic balloon pump in coronary patients with severe left ventricular dysfunction undergoing OPCAB surgery: early and mid-term outcomes.
2009 Jul 27
The role of phosphodiesterase 3 in endotoxin-induced acute kidney injury.
2009 Jun 1
Pharmacological interventions for ischaemia reperfusion injury in liver resection surgery performed under vascular control.
2009 Oct 7
Pharmacological interventions versus no pharmacological intervention for ischaemia reperfusion injury in liver resection surgery performed under vascular control.
2009 Oct 7
Patents

Sample Use Guides

Congestive heart failure IV Initially, 0.75 mg/kg as a slow (over 2–3 minutes) direct injection; if warranted, may administer a supplemental direct IV dose of 0.75 mg/kg 30 minutes after the initial dose.1 60 Direct IV injection is followed by an IV infusion of 5–10 mcg/kg per minute. Duration of therapy determined by clinical response and tolerance to adverse effects.
Route of Administration: Intravenous
Inamrinone inhibited human platelet aggregation at 10,800 s(-1) in a dose-dependent manner with the IC(50) value of 61 +/- 8 uM (mean +/- S.D.), Inamrinone significantly inhibited platelet aggregation at 1200 s(-1) only at highest concentration tested (100 uM)
Name Type Language
INAMRINONE
USAN   USP   VANDF  
USAN  
Official Name English
AMRINONE [MI]
Common Name English
5-AMINO(3,4'-BIPYRIDIN)-6(1H)-ONE
Systematic Name English
INAMRINONE [USP MONOGRAPH]
Common Name English
AMRINONE
INN   JAN   MART.   MI   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
AMRINONE [MART.]
Common Name English
C01CE01
Code English
INAMRINONE [USAN]
Common Name English
WINCORAM
Brand Name English
5-AMINO-3,4'-BIPYRIDYL-6(1H)-ONE
Systematic Name English
AMRINONE [USP-RS]
Common Name English
CORDEMCURA
Brand Name English
NSC-759805
Code English
VESISTOL
Brand Name English
WIN-40680
Code English
INAMRINONE [VANDF]
Common Name English
WIN 40680
Code English
INAMRINONE [USP]
Common Name English
CARTONIC
Brand Name English
AMRINONE [VANDF]
Common Name English
AMCORAL
Brand Name English
(3,4'-BIPYRIDIN)-6(1H)-ONE, 5-AMINO-
Systematic Name English
AMRINONE [INN]
Common Name English
AMRINONE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QC01CE01
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
WHO-ATC C01CE01
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
NCI_THESAURUS C29707
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
NCI_THESAURUS C744
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
Code System Code Type Description
MESH
D000676
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY
ChEMBL
CHEMBL12856
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY
PUBCHEM
3698
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY
USP_CATALOG
1034308
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY USP-RS
INN
4310
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY
EVMPD
SUB05493MIG
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY
WIKIPEDIA
AMRINONE
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY
DRUG CENTRAL
201
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY
DRUG BANK
DB01427
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY
FDA UNII
JUT23379TN
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY
CAS
60719-84-8
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY
IUPHAR
7202
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY
NCI_THESAURUS
C61789
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY
EPA CompTox
60719-84-8
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY
MERCK INDEX
M1857
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
262-390-0
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY
RXCUI
738
Created by admin on Fri Jun 25 21:02:42 UTC 2021 , Edited by admin on Fri Jun 25 21:02:42 UTC 2021
PRIMARY RxNorm