Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C19H18N4O2 |
| Molecular Weight | 334.3725 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1CC(=NN=C1c2ccc3c(c2)nc(-c4ccc(cc4)OC)[nH]3)O
InChI
InChIKey=GLBJJMFZWDBELO-UHFFFAOYSA-N
InChI=1S/C19H18N4O2/c1-11-9-17(24)22-23-18(11)13-5-8-15-16(10-13)21-19(20-15)12-3-6-14(25-2)7-4-12/h3-8,10-11H,9H2,1-2H3,(H,20,21)(H,22,24)
| Molecular Formula | C19H18N4O2 |
| Molecular Weight | 334.3725 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
DescriptionCurator's Comment:: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/1660359
Curator's Comment:: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/1660359
Pimobendan (INN, or pimobendane; tradenames Vetmedin, Acardi, and Heartmedin) is a veterinary medication. Under the trade name Acardi, it is available for human use in Japan. Usually, this medicine is used to treat acute heart failure and chronic heart failure (mild to moderate in severity). By increasing the calcium ion sensitivity to protein regulating myocardial contraction and also by inhibiting phosphodiesterase (PDE-III) activity, this medicine dilates the blood vessels and improves the symptoms of heart failure such as shortness of breath and difficulty in breathing. Pimobendan is metabolized into an active metabolite (desmethylpimobendan) by the liver. The parent compound, pimobendan, is a potent calcium sensitizer while desmethylpimobendan is a more potent phosphodiesterase III inhibitor. Pimobendan is 90–95% bound to plasma proteins in circulation. This may have implications in patients suffering from low blood protein levels (hypoproteinemia/hypoalbuminemia) and in patients that are on concurrent therapies that are also highly protein bound.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Differential modulation of cytokine production by drugs: implications for therapy in heart failure. | 1996 Dec |
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| The novel insulinotropic mechanism of pimobendan: direct enhancement of the exocytotic process of insulin secretory granules by increased Ca2+ sensitivity in beta-cells. | 1998 Mar |
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| A case of severe hypoglycemia due to pimobendan. | 2001 Aug |
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| Beneficial effects of the Ca2+ sensitizer EMD 57033 in exercising pigs with infarction-induced chronic left ventricular dysfunction. | 2001 Oct |
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| Decrease in Ca(2+)-sensitizing effect of UD-CG 212 Cl, a metabolite of pimobendan, under acidotic condition in canine ventricular myocardium. | 2001 Sep |
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| Effect of pimobendan in patients with chronic heart failure. | 2001 Winter |
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| Normalization of left ventricular parameters following combined pimobendan and carvedilol treatment in a case of unclassified cardiomyopathy with longstanding refractory status. | 2002 Dec |
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| Beta-blocker therapy combined with low-dose pimobendan in patients with idiopathic dilated cardiomyopathy and chronic obstructive pulmonary disease: report on two cases. | 2002 May |
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| A double-blind, randomized, placebo-controlled study of pimobendan in dogs with dilated cardiomyopathy. | 2002 May-Jun |
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| Low-dose systemic phosphodiesterase III inhibitor pimobendan combined with prostacyclin therapy in a patient with severe primary pulmonary hypertension. | 2003 Jul |
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| Role of nonglycosidic inotropic agents: indications, ethics, and limitations. | 2003 Mar |
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| Inhibition and facilitation by pimobendan, a calcium sensitizer, of catecholamine secretion from bovine adrenal chromaffin cells. | 2003 Mar |
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| [Inotropic agents]. | 2003 May |
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| [Roles of cytokines in the pathogenesis of heart failure]. | 2003 May |
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| Treatment of congestive heart failure. | 2003 Nov |
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| [If the myofilaments become sensitive: Ca2+-sensitizer for the therapy of heart insufficiency]. | 2005 Apr 15 |
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| [Cytokine antagonists and endothelin antagonists for therapy of heart failure]. | 2005 Feb 10 |
|
| Efficacy and safet of pimobendan in canine heart failure caused by myxomatous mitral valve disease. | 2005 Mar |
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| A review of levosimendan in the treatment of heart failure. | 2006 |
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| Positive inotropic effect of purified green tea catechin derivative in guinea pig hearts: the measurements of cellular Ca2+ and nitric oxide release. | 2006 Dec 15 |
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| [Subarachnoid hemorrhage complicated with different manifestations of transient abnormal left ventricular wall motion: two case reports]. | 2006 May |
|
| Preclinical dilated cardiomyopathy in the dobermann. | 2006 May 27 |
|
| New insights in the treatment strategy for pulmonary arterial hypertension. | 2006 Oct |
|
| Effects of pimobendan for mitral valve regurgitation in dogs. | 2007 Apr |
|
| A pilot study to assess the feasibility of a submaximal exercise test to measure individual response to cardiac medication in dogs with acquired heart failure. | 2007 Aug |
|
| Comparative adverse cardiac effects of pimobendan and benazepril monotherapy in dogs with mild degenerative mitral valve disease: a prospective, controlled, blinded, and randomized study. | 2007 Jul-Aug |
|
| [Calcium sensitizer agents in heart failure therapy]. | 2007 May 28 |
|
| [Phosphodiesterase III inhibitor--characteristics, mechanisms of action, pharmacokinetics, indications, contraindications, clinical trials, and side effects]. | 2007 May 28 |
|
| [Calcium sensitizer: characteristics, mechanisms of action, pharmacokinetics, indication, contraindication, clinical data, and side effects]. | 2007 May 28 |
|
| Effect of short-term treatment with meloxicam and pimobendan on the renal function in healthy beagle dogs. | 2008 Apr |
|
| Cardiac Ca2+ signaling and Ca2+ sensitizers. | 2008 Dec |
|
| Defining the binding site of levosimendan and its analogues in a regulatory cardiac troponin C-troponin I complex. | 2008 Jul 15 |
|
| The role of cardiac troponin T quantity and function in cardiac development and dilated cardiomyopathy. | 2008 Jul 9 |
|
| Effect of pimobendan on case fatality rate in Doberman Pinschers with congestive heart failure caused by dilated cardiomyopathy. | 2008 Jul-Aug |
|
| Anaesthesia for the geriatric dog and cat. | 2008 Jun 1 |
|
| Concerns about "Comparative adverse cardiac effects of pimobendan and benazepril monotherapy in dogs with mild degenerative mitral valve disease". | 2008 Mar-Apr |
|
| Concerns about "Comparative adverse cardiac effects of pimobendan and benazepril monotherapy in dogs with mild degenerative mitral valve disease: a prospective, controlled, blinded and randomized study". | 2008 Mar-Apr |
|
| Alterations in vasomotor control of coronary resistance vessels in remodelled myocardium of swine with a recent myocardial infarction. | 2008 May |
|
| Treatment of congestive heart failure in dogs. | 2008 Oct 25 |
|
| Effect of pimobendan or benazepril hydrochloride on survival times in dogs with congestive heart failure caused by naturally occurring myxomatous mitral valve disease: the QUEST study. | 2008 Sep-Oct |
|
| Agents with inotropic properties for the management of acute heart failure syndromes. Traditional agents and beyond. | 2009 Dec |
|
| Acute effect of pimobendan and furosemide on the circulating renin-angiotensin-aldosterone system in healthy dogs. | 2009 Sep-Oct |
|
| Sarcomere control mechanisms and the dynamics of the cardiac cycle. | 2010 |
|
| Canine dilated cardiomyopathy: a retrospective study of prognostic findings in 367 clinical cases. | 2010 Aug |
|
| Patients' self-assessed functional status in heart failure by New York Heart Association class: a prognostic predictor of hospitalizations, quality of life and death. | 2010 Feb |
|
| Synthesis of new 4,5-3(2H)pyridazinone derivatives and their cardiotonic, hypotensive, and platelet aggregation inhibition activities. | 2010 Jan |
|
| Human cardiac tissue in a microperfusion chamber simulating extracorporeal circulation--ischemia and apoptosis studies. | 2010 Jan 18 |
|
| Canine degenerative myxomatous mitral valve disease: natural history, clinical presentation and therapy. | 2010 Jul |
|
| Current use of pimobendan in canine patients with heart disease. | 2010 Jul |
|
| Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model. | 2013 Dec |
Sample Use Guides
Acute heart failure: usually for adults, one capsule (2.5 mg of pimobendan) once daily
Chronic heart failure (mild to moderate in severity): usually for adults, one capsule (2.5 mg of pimobendan) twice daily after meals
Route of Administration:
Oral
composite platelet aggregation (area under the curve [AUC]) and maximal platelet aggregation (aggregation units [AUs]) at 10.0μM pimobendan were significantly decreased for collagen-induced aggregation (AUC, 349.7 ± 58.4 vs 285.1 ± 72.2; maximal platelet aggregation, 196.2 ± 25.8 AUs vs 161.5 ± 38.0 AUs), and the AUC and velocity of aggregation at 10.0μM pimobendan were significantly decreased for ADP-induced aggregation (AUC, 268.5 ± 35.1 vs 213.4 ± 77.2; velocity of aggregation, 15.7 ± 2.9 AUs/min vs 11.8 ± 3.5 AUs/min).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 12:40:43 UTC 2021
by
admin
on
Sat Jun 26 12:40:43 UTC 2021
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| Record UNII |
34AP3BBP9T
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| Record Status |
Validated (UNII)
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| Record Version |
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CFR |
21 CFR 520.1780
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EMA VETERINARY ASSESSMENT REPORTS |
FORTEKOR PLUS (AUTHORISED)
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NCI_THESAURUS |
C744
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1569315
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34AP3BBP9T
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PIMOBENDAN
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SUB09845MIG
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118428-36-7
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CHEMBL24646
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2171
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C041648
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M8815
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DB11450
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C82305
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74150-27-9
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5090
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1110783
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4823
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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| Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
| Related Record | Type | Details | ||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
