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

Molecular Formula C10H9N3O
Molecular Weight 187.1983
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

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
Lack of role for nitric oxide in cholinergic modulation of myocardial contractility in vivo.
2001 Jul
[Randomized controlled trial for the effect of amrinone and aprotinin on proinflammatory cytokine release in patients with prosthetic valve replacement during perioperative period].
2001 Jun
Role of cyclic nucleotides in ischemia and reperfusion injury of canine livers.
2002 Apr 15
Effects of cAMP modulators on long-chain fatty-acid uptake and utilization by electrically stimulated rat cardiac myocytes.
2002 Nov 1
[Effect of dexamethasone, aminoguanidin, amrinone on oxygen utilization in endotoxin shock rabbits].
2003 Apr
Development of an in vitro model for vascular injury with human endothelial cells.
2004
Diminished inotropic response to amrinone in ventricular myocytes from myopathic hamsters is linked to depression of high-gain Ca2+-induced Ca2+ release.
2004 Aug
Differential pharmacologic sensitivities of phosphodiesterase-3 inhibitors among human isolated gastroepiploic, internal mammary, and radial arteries.
2005 Oct
Alkaline Phosphatases : Structure, substrate specificity and functional relatedness to other members of a large superfamily of enzymes.
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
Cirrhotic cardiomyopathy.
2007 Mar 27
Peripartum cardiomyopathy: review of the literature.
2007 Oct 31
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
Drug effect unveils inter-head cooperativity and strain-dependent ADP release in fast skeletal actomyosin.
2009 Aug 21
Agents with inotropic properties for the management of acute heart failure syndromes. Traditional agents and beyond.
2009 Dec
Effects of amrinone in an experimental model of hepatic ischemia-reperfusion injury.
2009 Jan
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 Fri Jun 25 21:02:42 UTC 2021
Edited
by admin
on Fri Jun 25 21:02:42 UTC 2021
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
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
Related Record Type Details
ACTIVE MOIETY