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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
Differential modulation of cytokine production by drugs: implications for therapy in heart failure.
1996 Dec
Identification of cytochrome P-450 isoform(s) responsible for the metabolism of pimobendan in human liver microsomes.
2000 Jan
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
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
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
Inhibition and facilitation by pimobendan, a calcium sensitizer, of catecholamine secretion from bovine adrenal chromaffin cells.
2003 Mar
Plasma concentration profile of orally administered pimobendan and plasma brain natriuretic peptide level in patients with severe heart failure.
2003 May
[Inotropic agents].
2003 May
The role of Ca++-sensitizers for the treatment of heart failure.
2003 Oct
Ca2+-sensitisers--a promising option to treat heart failure?
2005 Dec
Effect of pimobendan on cardiopulmonary baroreflex control of sympathetic nerve activity in healthy young men.
2005 Oct 30
Clinical efficacy of pimobendan versus benazepril for the treatment of acquired atrioventricular valvular disease in dogs.
2006 Jul-Aug
Syncope secondary to transient atrioventricular block in a German shepherd dog with dilated cardiomyopathy and atrial fibrillation.
2006 May
Preclinical dilated cardiomyopathy in the dobermann.
2006 May 27
Acute heart failure: inotropic agents and their clinical uses.
2006 Nov
Beta-blockers use in patients with chronic obstructive pulmonary disease and concomitant cardiovascular conditions.
2007
Effects of pimobendan for mitral valve regurgitation in dogs.
2007 Apr
[Combined therapy with weight loss and amiodarone improved cardiac function in a patient with idiopathic dilated cardiomyopathy complicated with severe obesity: a case report].
2007 Aug
Knock-in mouse model of dilated cardiomyopathy caused by troponin mutation.
2007 Jul 20
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
[Phosphodiesterase III inhibitor--characteristics, mechanisms of action, pharmacokinetics, indications, contraindications, clinical trials, and side effects].
2007 May 28
Treatment options in myocarditis: what we know from experimental data and how it translates to clinical trials.
2007 Sep
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
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
Validity, reliability, and responsiveness of the Kansas City Cardiomyopathy Questionnaire in anemic heart failure patients.
2008 Mar
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
Canine heart disease: progress and promise.
2008 Nov
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
Evaluation of pimobendan and N-terminal probrain natriuretic peptide in the treatment of pulmonary hypertension secondary to degenerative mitral valve disease in dogs.
2009 Nov-Dec
Readability estimates for commonly used health-related quality of life surveys.
2009 Sep
Assessment of the pharmacological effects of inotropic drugs on left ventricular pressure and contractility: an evaluation of the QA interval as an indirect indicator of cardiac inotropism.
2009 Sep-Oct
Canine dilated cardiomyopathy: a retrospective study of prognostic findings in 367 clinical cases.
2010 Aug
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