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
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)
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 |
DescriptionSources: http://www.drugbank.ca/drugs/DB01427Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/inamrinone.html
Sources: http://www.drugbank.ca/drugs/DB01427
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL241 Sources: http://www.drugbank.ca/drugs/DB01427 |
16.7 µM [IC50] | ||
Target ID: CHEMBL290 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10644042 |
31.2 µM [IC50] | ||
Target ID: GO:0070527 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14698653 |
61.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | AMRINONE LACTATE Approved UseFor the short-term management of congestive heart failure. Launch Date2000 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8513658/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
245 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8513658/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8513658/ |
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
Dose | Population | Adverse 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... Other AEs: Death (grade 5) Sources: |
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 Sources: Cardiac arrest Respiratory distress syndrome Chest pain Palpitations Ventricular ectopic beats |
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 Sources: Thrombocytopenia |
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
AE | Significance | Dose | Population |
---|---|---|---|
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: |
PubMed
Title | Date | PubMed |
---|---|---|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14698653
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
Edited
Sat Dec 16 17:50:11 GMT 2023
by
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Sat Dec 16 17:50:11 GMT 2023
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Record UNII |
JUT23379TN
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QC01CE01
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C01CE01
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NCI_THESAURUS |
C29707
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NCI_THESAURUS |
C744
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D000676
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CHEMBL12856
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3698
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4310
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SUB05493MIG
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AMRINONE
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DB01427
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JUT23379TN
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60719-84-8
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7202
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C61789
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2686
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m1857
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262-390-0
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759805
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738
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