OLPRINONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H10N4O
Molecular Weight	250.2554
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(C=C(C#N)C(=O)N1)C2=CN3C=CN=C3C=C2

InChI

InChIKey=JPAWFIIYTJQOKW-UHFFFAOYSA-N

InChI=1S/C14H10N4O/c1-9-12(6-11(7-15)14(19)17-9)10-2-3-13-16-4-5-18(13)8-10/h2-6,8H,1H3,(H,17,19)

HIDE SMILES / InChI

Molecular Formula	C14H10N4O
Molecular Weight	250.2554
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/2566308
Curator's Comment: description was created based on several sources, including http://www.eisai.jp/medical/products/di/EPI/COR_A_EPI.pdf

Olprinone (INN) is a cardiotonic agent, is used for treatment acute heart failure. It has been marketed in Japan since 1996. The main mechanism of action of olprinone hydrochloride hydrate is selective inhibition of PDE III specific to cAMP. It is considered that this action causes an increase in intracellular cAMP levels and peak Ca2+ levels, thereby increasing myocardial contractility.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 3 61 Target ID: CHEMBL2094125 Sources: http://www.ncbi.nlm.nih.gov/pubmed/2566308	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute heart failure 9 Sources: http://www.eisai.jp/medical/products/di/EPI/COR_A_EPI.pdf	Primary		Approved 8583	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
13.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23690065/	5 μg/kg bw single, intravenous dose: 5 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		OLPRINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
8.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23690065/	5 μg/kg bw single, intravenous dose: 5 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		OLPRINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.55 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23690065/	5 μg/kg bw single, intravenous dose: 5 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		OLPRINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
18.7% EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/21/3/21_3_613/_article/-char/en	50 μg/kg bw single, intravenous dose: 50 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		OLPRINONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
0.4 ug/kg/min single, intravenous Highest studied dose Dose: 0.4 ug/kg/min Route: intravenous Route: single Dose: 0.4 ug/kg/min Sources: https://pubmed.ncbi.nlm.nih.gov/21326107/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/21326107/	Sources: https://pubmed.ncbi.nlm.nih.gov/21326107/
0.1 ug/kg/min single, intravenous Studied dose Dose: 0.1 ug/kg/min Route: intravenous Route: single Dose: 0.1 ug/kg/min Sources: https://pubmed.ncbi.nlm.nih.gov/28028637/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28028637/	Sources: https://pubmed.ncbi.nlm.nih.gov/28028637/

PubMed

Title	Date	PubMed
Ethyl 8-(4-nitro-phen-yl)imidazo[1,2-a]pyridine-7-carboxyl-ate.	2010-11-24	21589555
Olprinone attenuates the acute inflammatory response and apoptosis after spinal cord trauma in mice.	2010-09-07	20830289
Olprinone attenuates the development of ischemia/reperfusion injury of the gut.	2010-07	20349038
A phosphodiesterase III inhibitor protects rat liver from sinusoidal obstruction syndrome through heme oxygenase-1 induction.	2010-04	20224351
Anesthetic management of a patient undergoing liver transplantation who had previous coronary artery bypass grafting using an in situ right gastroepiploic artery.	2010-04	20191293
Effect of olprinone, a phosphodiesterase III inhibitor, on hepatic ischemia-reperfusion injury in rats.	2010-04	19730166
The effects of the phosphodiesterase inhibitor olprinone on global cerebral ischemia.	2010-03-01	20042441
Differential vasodilation response to olprinone in rabbit renal and common carotid arteries.	2010-02	20175287
[Right heart failure during modified ultrafiltration in pediatric living donor lobar lung transplantation].	2010-02	20169963
Local application of olprinone for promotion of peripheral nerve regeneration.	2009-11	19997829
Pharmacological preconditioning in type 2 diabetic rat hearts: the roles of mitochondrial ATP-sensitive potassium channels and the phosphatidylinositol 3-kinase-Akt pathway.	2009-08	19597978
A phosphodiesterase III inhibitor protects rat liver from sinusoidal obstruction syndrome through heme oxygenase-1 induction.	2009-05	19387321
[Use of cardiovascular drugs for cardiac surgery--based on recent studies].	2009-03	19306627
[A case report of anesthesia for a child with Pompe's disease (glycogen storage disease type II)].	2009-02	19227183
The phosphodiesterase III inhibitor olprinone inhibits hippocampal glutamate release via a cGMP/PKG pathway.	2008-12-26	18983890
Chemical-genetic profiling of imidazo[1,2-a]pyridines and -pyrimidines reveals target pathways conserved between yeast and human cells.	2008-11	19043571
[The effect of PDEIII inhibitors and colforsin daropate on hypoxic pulmonary vasoconstriction in rabbit lungs].	2008-11	19039966
[Anesthetic management of coronary artery bypass grafting for unstable angina pectoris in a patient undergoing home oxygen therapy].	2008-04	18416197
Clinically relevant concentrations of olprinone reverse attenuating effect of propofol on isoproterenol-induced cyclic adenosine monophosphate accumulation in cardiomyocytes.	2008-03	18578361
ABCD of the phosphodiesterase family: interaction and differential activity in COPD.	2008	19281073
Olprinone decreases elevated concentrations of cytokine-induced neutrophil chemoattractant-1 in septic rats.	2008	18306010
Pretreatment with olprinone hydrochloride, a phosphodiesterase III inhibitor, attenuates lipopolysaccharide-induced lung injury via an anti-inflammatory effect.	2008	17434327
Effects of olprinone on neuromuscular blockade caused by vecuronium.	2007-12	18402286
The effects of vasoactive agents, platelet agonists and anticoagulation on thrombelastography.	2007-10	17850565
[How to use PDE III inhibitors].	2007-05-28	17571365
[Phosphodiesterase III inhibitor--characteristics, mechanisms of action, pharmacokinetics, indications, contraindications, clinical trials, and side effects].	2007-05-28	17571364
[Infusion therapy at outpatient clinic in chronic end-stage heart failure].	2007-05	17552290
Effects of olprinone, a phosphodiesterase III inhibitor, on ischemic acute renal failure.	2007-03	17430259
Child with fulminant myocarditis survived by ECMO Support--report of a child case.	2007-02	17392676
Metabolic effects of phosphodiesterase III inhibitors: another reason to promote their use?	2007	17572916
Cardioprotection induced by olprinone, a phosphodiesterase III inhibitor, involves phosphatidylinositol-3-OH kinase-Akt and a mitochondrial permeability transition pore during early reperfusion.	2007	17458647
Selective inhibitors for phosphodiesterase 3 and 4 in antigen-induced increase of cough reflex sensitivity in guinea pigs.	2007	16829147
Acute heart failure: inotropic agents and their clinical uses.	2006-11	17059376
Effects of olprinone on myocardial ischemia-reperfusion injury in dogs.	2006-08	16953089
The enhancement of cellular cAMP with olprinone protects autotransplanted rat kidney against cold ischemia-reperfusion injury.	2006-06	16797361
Effects of dopamine and olprinone on ventricular energetics in sevoflurane-induced acute left ventricular depression in dogs.	2006-06	16750736
Vasoactive drugs and the gut: is there anything new?	2006-04	16543793
[Effects of olprinone hydrochloride in patients undergoing off-pump coronary artery bypass grafting].	2006-02	16491891
The effects of olprinone, a phosphodiesterase 3 inhibitor, on systemic and cerebral circulation.	2006-01	16472171
Effects of a phosphodiesterase 3 inhibitor, olprinone, on rhythmical change in tension of human gastroepiploic artery.	2005-12-28	16325808
Phosphodiesterase 3 inhibition and cough in elderly asthmatics.	2005-11-24	16307683
Differential pharmacologic sensitivities of phosphodiesterase-3 inhibitors among human isolated gastroepiploic, internal mammary, and radial arteries.	2005-10	16192501
Olprinone reduces ischemia/reperfusion-induced acute renal injury in rats through enhancement of cAMP.	2005-09	16135969
[Successful anesthetic management of three patients with cardiac dysfunction for non-cardiac surgery using olprinone hydrochloride].	2005-07	16026056
Effects of phosphodiesterase-III inhibitors on sevoflurane-induced impairment of rat diaphragmatic function.	2005-07	15954966
Bench-to-bedside review: Inotropic drug therapy after adult cardiac surgery -- a systematic literature review.	2005-06	15987381
[Anesthetic management for an infant with tetralogy of fallot with absent pulmonary valve].	2005-02	15747515
Effects of olprinone on hepatosplanchnic circulation and mitochondrial oxidation in a porcine model of endotoxemia.	2005	16261466
The phosphodiesterase III inhibitor olprinone decreases sensitivity of rat Kupffer cells to endotoxin.	2004-08	15318102
Pharmacokinetics and pharmacodynamics of olprinone after cardiac surgery.	2004-06	15646253

Patents

Sample Use Guides

In Vivo Use Guide

intravenously at a dose of 10 µg/kg of olprinone hydrochloride hydrate, gradually over 5 min, and then drip-infused intravenously at a rate of 0.1 - 0.3 µg/kg/min

Route of Administration: Intravenous

In Vitro Use Guide

E-1020 (Olprinone) may improve diastolic function as well as systolic function in failing hearts. Effects of E-1020, on intracellular calcium transients were compared with those of isoproterenol (ISO) in isolated single myocytes from failing hearts secondary to pulmonary hypertension induced by monocrotaline injection. Myocytes were isolated by enzyme digestion using a Langendorff apparatus. Changes in intracellular calcium concentrations ([Ca2+]i) were recorded using a fura-2 fluorescence microscopic technique.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:37:02 GMT 2025` Edited by `admin` on `Wed Apr 02 09:37:02 GMT 2025`
Record UNII	4Y8BMI9YGC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1,2-DIHYDRO-5-IMIDAZO(1,2-.ALPHA.)PYRIDIN-6-YL-6-METHYL-2-OXONICOTINONITRILE

Preferred Name

English

OLPRINONE

Official Name

English

Olprinone [WHO-DD]

Common Name

English

LOPRINONE [MI]

Common Name

English

olprinone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C744