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

Details

Stereochemistry ACHIRAL
Molecular Formula C10H9N3O
Molecular Weight 187.198
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INAMRINONE

SMILES

NC1=CC(=CNC1=O)C2=CC=NC=C2

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

Molecular Formula C10H9N3O
Molecular Weight 187.198
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/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

2000
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
Reversal of propranolol blockade of adrenergic receptors and related toxicity with drugs that increase cyclic AMP.
1999 Sep
Effects of the specific phosphodiesterase inhibitors on alloxan-induced diabetic rabbit cavernous tissue in vitro.
2001 Feb
Amrinone can accelerate the cooling rate of core temperature during deliberate mild hypothermia for neurosurgical procedures.
2001 May
Comparison of enoximone, amrinone, or levosimendan enriched St. Thomas' hospital cardioplegic solutions used for myocardial preservation in isolated guinea pig hearts.
2002
Role of cyclic nucleotides in ischemia and reperfusion injury of canine livers.
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
Intraoperative insulin therapy does not reduce the need for inotropic or antiarrhythmic therapy after cardiopulmonary bypass.
2002 Aug
Immunopharmacological potential of selective phosphodiesterase inhibition. II. Evidence for the involvement of an inhibitory-kappaB/nuclear factor-kappaB-sensitive pathway in alveolar epithelial cells.
2002 Feb
High-dose amrinone is required to accelerate rewarming from deliberate mild intraoperative hypothermia for neurosurgical procedures.
2002 Jul
Mechanisms of leptin secretion from white adipocytes.
2002 Jul
[Effects of amrinone in patients undergoing off-pump coronary artery bypass grafting].
2002 May
Effects of preemptive therapy with milrinone or amrinone on perioperative platelet function and haemostasis in patients undergoing coronary bypass grafting.
2003 Aug
Interleukin-6 family of cytokines mediates isoproterenol-induced delayed STAT3 activation in mouse heart.
2003 Jun 6
Treatment of mechanically-induced vasospasm of the carotid artery in a primate using intra-arterial verapamil: a technical case report.
2004 Jul 21
Successful allogeneic bone marrow transplantation for acute myelogenous leukemia after drug-induced cardiomyopathy.
2004 Sep
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
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
Alkaline Phosphatases : Structure, substrate specificity and functional relatedness to other members of a large superfamily of enzymes.
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
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
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
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)
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:50:11 GMT 2023
Edited
by admin
on Sat Dec 16 17:50:11 GMT 2023
Record UNII
JUT23379TN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INAMRINONE
USAN   USP   VANDF  
USAN  
Official Name English
AMRINONE [MI]
Common Name English
AMRINONE [JAN]
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
Amrinone [WHO-DD]
Common Name English
INAMRINONE [VANDF]
Common Name English
WIN 40680
Code English
INAMRINONE [USP IMPURITY]
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
Classification Tree Code System Code
WHO-VATC QC01CE01
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
WHO-ATC C01CE01
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
NCI_THESAURUS C29707
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
NCI_THESAURUS C744
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
Code System Code Type Description
MESH
D000676
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
ChEMBL
CHEMBL12856
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
PUBCHEM
3698
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
INN
4310
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
EVMPD
SUB05493MIG
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
WIKIPEDIA
AMRINONE
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
DRUG CENTRAL
201
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
DRUG BANK
DB01427
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
FDA UNII
JUT23379TN
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
CAS
60719-84-8
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
SMS_ID
100000086917
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
IUPHAR
7202
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
NCI_THESAURUS
C61789
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
CHEBI
2686
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
RS_ITEM_NUM
1034308
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID9022603
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
MERCK INDEX
m1857
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
262-390-0
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
NSC
759805
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY
RXCUI
738
Created by admin on Sat Dec 16 17:50:11 GMT 2023 , Edited by admin on Sat Dec 16 17:50:11 GMT 2023
PRIMARY RxNorm
Related Record Type Details
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