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

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
Poisoning with calcium channel blockers--a case report and review of the literature.
2001 Dec
Clinical use of amrinone (a selective phosphodiesterase III inhibitor) in reconstructive surgery.
2001 Dec
Effects of the specific phosphodiesterase inhibitors on alloxan-induced diabetic rabbit cavernous tissue in vitro.
2001 Feb
Lack of role for nitric oxide in cholinergic modulation of myocardial contractility in vivo.
2001 Jul
The efficacy of preemptive Milrinone or Amrinone therapy in patients undergoing coronary artery bypass grafting.
2002 Jan
[Effects of amrinone in patients undergoing off-pump coronary artery bypass grafting].
2002 May
Differential effects of amrinone and milrinone upon myocardial inflammatory signaling.
2002 Sep 24
Possible contribution of acetylamrinone and its enhancing effects on platelet aggregation under shear stress conditions in the onset of thrombocytopenia in patients treated with amrinone.
2003
Effects of preemptive therapy with milrinone or amrinone on perioperative platelet function and haemostasis in patients undergoing coronary bypass grafting.
2003 Aug
[Levosimendan: a new option in the pharmacologic management of cardiac insufficiency].
2003 Jan-Feb
Inhibition and facilitation by pimobendan, a calcium sensitizer, of catecholamine secretion from bovine adrenal chromaffin cells.
2003 Mar
Development of an in vitro model for vascular injury with human endothelial cells.
2004
Cardiac and vascular effects of diltiazem, dobutamine and amrinone, drugs used after myocardial revascularization.
2004 Jun
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
Inotropic responses to phosphodiesterase inhibitors in cardiac hypertrophy in rats.
2005 May 9
Effects of inotropic drugs on mechanical function and oxygen balance in postischemic canine myocardium: comparison of dobutamine, epinephrine, amrinone, and calcium chloride.
2005 Oct
Bench-to-bedside review: thrombocytopenia-associated multiple organ failure--a newly appreciated syndrome in the critically ill.
2006
In vivo dilatation of the fetal and postnatal ductus arteriosus by inhibition of phosphodiesterase 3 in rats.
2006
A comparison of three phosphodiesterase type III inhibitors on mechanical and metabolic function in guinea pig isolated hearts.
2006 Jun
The base exchange reaction of NAD+ glycohydrolase: identification of novel heterocyclic alternative substrates.
2008 Nov 15
Effect of nitric oxide/cyclic guanosine mono-phosphate pathway on gallbladder relaxant response in bile duct-ligated guinea pigs.
2009
Effects of propofol on responses of rat isolated renal arteriole to vasoactive agents.
2009 Aug-Sep
Gene expression analysis reveals new possible mechanisms of vancomycin-induced nephrotoxicity and identifies gene markers candidates.
2009 Jan
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
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