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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
Structure of PIMOBENDAN

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)

HIDE SMILES / InChI

Description
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.

Originator

Curator's Comment:: # Boehringer Ingelheim Pharma KG

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: sensitization of the contractile proteins to Ca2+
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Identification of cytochrome P-450 isoform(s) responsible for the metabolism of pimobendan in human liver microsomes.
2000 Jan
A case of severe hypoglycemia due to pimobendan.
2001 Aug
Effects of Ca2+ sensitizers on contraction, [Ca2+]i transient and myofilament Ca2+ sensitivity in diabetic rat myocardium: potential usefulness as inotropic agents.
2001 Aug
New pharmacological strategies for the treatment of heart failure.
2001 Jul
The role of inflammatory mediators in the failing heart: immunomodulation of cytokines in experimental models of heart failure.
2001 Mar
Beneficial effects of the Ca2+ sensitizer EMD 57033 in exercising pigs with infarction-induced chronic left ventricular dysfunction.
2001 Oct
Mechanism of action of Ca2+ sensitizers--update 2001.
2001 Sep
Decrease in Ca(2+)-sensitizing effect of UD-CG 212 Cl, a metabolite of pimobendan, under acidotic condition in canine ventricular myocardium.
2001 Sep
Disparate force-frequency effects of pimobendan and dobutamine in conscious dogs with tachycardia-induced cardiomyopathy.
2002 Dec
Normalization of left ventricular parameters following combined pimobendan and carvedilol treatment in a case of unclassified cardiomyopathy with longstanding refractory status.
2002 Dec
Effects of pimobendan on adverse cardiac events and physical activities in patients with mild to moderate chronic heart failure: the effects of pimobendan on chronic heart failure study (EPOCH study).
2002 Feb
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
Inotropic agents and immune modulation.
2002 May
A double-blind, randomized, placebo-controlled study of pimobendan in dogs with dilated cardiomyopathy.
2002 May-Jun
Combined endpoints: can we use them?
2002 Oct 15
Mechanisms of action of novel cardiotonic agents.
2002 Sep
Low-dose systemic phosphodiesterase III inhibitor pimobendan combined with prostacyclin therapy in a patient with severe primary pulmonary hypertension.
2003 Jul
Role of nonglycosidic inotropic agents: indications, ethics, and limitations.
2003 Mar
Inhibition and facilitation by pimobendan, a calcium sensitizer, of catecholamine secretion from bovine adrenal chromaffin cells.
2003 Mar
Effects of rolipram, pimobendan and zaprinast on ischaemia-induced dysrhythmias and on ventricular cyclic nucleotide content in the anaesthetized rat.
2003 Mar
Plasma concentration profile of orally administered pimobendan and plasma brain natriuretic peptide level in patients with severe heart failure.
2003 May
[Roles of cytokines in the pathogenesis of heart failure].
2003 May
Do medical house officers value the health of veterans differently from the health of non-veterans?
2004 Apr 7
Successful allogeneic bone marrow transplantation for acute myelogenous leukemia after drug-induced cardiomyopathy.
2004 Sep
Use of pimobendan in the management of heart failure.
2004 Sep
Increased mitral valve regurgitation and myocardial hypertrophy in two dogs with long-term pimobendan therapy.
2005
[Cytokine antagonists and endothelin antagonists for therapy of heart failure].
2005 Feb 10
Pharmacokinetic characterization of transcellular transport and drug interaction of digoxin in Caco-2 cell monolayers.
2005 Jan
A review of levosimendan in the treatment of heart failure.
2006
Clinical efficacy of pimobendan versus benazepril for the treatment of acquired atrioventricular valvular disease in dogs.
2006 Jul-Aug
Acute heart failure: inotropic agents and their clinical uses.
2006 Nov
New insights in the treatment strategy for pulmonary arterial hypertension.
2006 Oct
Beta-blockers use in patients with chronic obstructive pulmonary disease and concomitant cardiovascular conditions.
2007
Knock-in mouse model of dilated cardiomyopathy caused by troponin mutation.
2007 Jul 20
[Phosphodiesterase III inhibitor--characteristics, mechanisms of action, pharmacokinetics, indications, contraindications, clinical trials, and side effects].
2007 May 28
Anaesthesia for the geriatric dog and cat.
2008 Jun 1
Alterations in vasomotor control of coronary resistance vessels in remodelled myocardium of swine with a recent myocardial infarction.
2008 May
Canine heart disease: progress and promise.
2008 Nov
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
Patents

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
In Vitro Use Guide
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).
Name Type Language
PIMOBENDAN
EP   GREEN BOOK   INN   JAN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
RACEMIC PIMOBENDAN
Common Name English
PIMOBENDAN [MART.]
Common Name English
PIMOBENDAN [EMA EPAR: VETERINARY]
Common Name English
PIMOBENDAN [WHO-DD]
Common Name English
PIMOBENDAN [MI]
Common Name English
VETMEDIN
Brand Name English
PIMOBENDAN [JAN]
Common Name English
3(2H)-PYRIDAZINONE, 4,5-DIHYDRO-6-(2-(4-METHOXYPHENYL)-1H-BENZIMIDAZOL-5-YL)-5-METHYL-, (+/-)-
Systematic Name English
FORTEKOR PLUS COMPONENT PIMOBENDAN
Brand Name English
PIMOBENDAN [USAN]
Common Name English
UD-CG-115
Code English
PIMOBENDAN [EP]
Common Name English
3(2H)-PYRIDAZINONE, 4,5-DIHYDRO-6-(2-(4-METHOXYPHENYL)-1H-BENZIMIDAZOL-6-YL)-5-METHYL-
Systematic Name English
PIMOBENDAN [USP-RS]
Common Name English
UD-CG-115BS
Code English
PIMOBENDAN [GREEN BOOK]
Common Name English
ACARDI
Brand Name English
UDCG-115
Code English
(+/-)-4,5-DIHYDRO-6-(2-(P-METHOXYPHENYL)-5-BENZIMIDAZOLYL)-5-METHYL-3(2H)-PYRIDAZINONE
Common Name English
PIMOBENDAN COMPONENT OF FORTEKOR PLUS
Common Name English
DL-PIMOBENDAN
Common Name English
PIMOBENDAN [USP MONOGRAPH]
Common Name English
PIMOBENDAN [INN]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 520.1780
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
EMA VETERINARY ASSESSMENT REPORTS FORTEKOR PLUS (AUTHORISED)
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
NCI_THESAURUS C744
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
Code System Code Type Description
USP_CATALOG
1569315
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
PRIMARY USP-RS
FDA UNII
34AP3BBP9T
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
PRIMARY
WIKIPEDIA
PIMOBENDAN
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
PRIMARY
EVMPD
SUB09845MIG
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
PRIMARY
CAS
118428-36-7
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
SUPERSEDED
ChEMBL
CHEMBL24646
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
PRIMARY
DRUG CENTRAL
2171
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
PRIMARY
MESH
C041648
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
PRIMARY
MERCK INDEX
M8815
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB11450
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
PRIMARY
NCI_THESAURUS
C82305
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
PRIMARY
CAS
74150-27-9
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
PRIMARY
INN
5090
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
PRIMARY
RXCUI
1110783
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
PRIMARY RxNorm
PUBCHEM
4823
Created by admin on Sat Jun 26 12:40:44 UTC 2021 , Edited by admin on Sat Jun 26 12:40:44 UTC 2021
PRIMARY