U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C19H18N4O2
Molecular Weight 334.3718
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIMOBENDAN

SMILES

COC1=CC=C(C=C1)C2=NC3=C(N2)C=CC(=C3)C4=NNC(=O)CC4C

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

Molecular Formula C19H18N4O2
Molecular Weight 334.3718
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
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
Effect of pimobendan in patients with chronic heart failure.
2001 Winter
A review of levosimendan in the treatment of heart failure.
2006
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
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
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
Translational medicine with a capital T, troponin T, that is.
2007 Jul 20
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
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
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
A QUEST begins.
2008 Sep-Oct
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
Cardiac sarcoidosis culminating in severe biventricular failure.
2009
Chronic cor pulmonale secondary to pulmonary atherosclerosis in an African Grey parrot.
2009 Apr 15
Agents with inotropic properties for the management of acute heart failure syndromes. Traditional agents and beyond.
2009 Dec
Effect of pimobendan on echocardiographic values in dogs with asymptomatic mitral valve disease.
2009 Mar-Apr
Transient tricuspid valve regurgitation following surgical treatment of cor triatriatum dexter in a dog.
2009 May
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
A randomized, double-blind, placebo-controlled study to determine the effects of valsartan on exercise time in patients with symptomatic heart failure with preserved ejection fraction.
2009 Oct
Readability estimates for commonly used health-related quality of life surveys.
2009 Sep
Acute effect of pimobendan and furosemide on the circulating renin-angiotensin-aldosterone system in healthy dogs.
2009 Sep-Oct
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
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
Synthesis, vasorelaxant activity and antihypertensive effect of benzo[d]imidazole derivatives.
2010 Jun 1
ECG of the month. Arrhythmogenic right ventricular cardiomyopathy in a Boxer.
2010 May 1
Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model.
2013 Dec
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).
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:47:38 UTC 2023
Edited
by admin
on Wed Jul 05 22:47:38 UTC 2023
Record UNII
34AP3BBP9T
Record Status Validated (UNII)
Record Version
  • Download
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 [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
Pimobendan [WHO-DD]
Common Name English
FORTEKOR PLUS COMPONENT PIMOBENDAN
Brand Name English
PIMOBENDAN [USAN]
Common Name English
UD-CG-115
Code English
PIMOBENDAN [EP IMPURITY]
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 Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
EMA VETERINARY ASSESSMENT REPORTS FORTEKOR PLUS (AUTHORISED)
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
NCI_THESAURUS C744
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
Code System Code Type Description
FDA UNII
34AP3BBP9T
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
WIKIPEDIA
PIMOBENDAN
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
USAN
DD-18
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
EVMPD
SUB09845MIG
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
CAS
118428-36-7
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
SUPERSEDED
RS_ITEM_NUM
1569315
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
ChEMBL
CHEMBL24646
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
SMS_ID
100000081974
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
DRUG CENTRAL
2171
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
MESH
C041648
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
MERCK INDEX
M8815
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY Merck Index
DAILYMED
34AP3BBP9T
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
DRUG BANK
DB11450
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
NCI_THESAURUS
C82305
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
CAS
74150-27-9
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
INN
5090
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
RXCUI
1110783
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY RxNorm
PUBCHEM
4823
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
CHEBI
32003
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID8048280
Created by admin on Wed Jul 05 22:47:38 UTC 2023 , Edited by admin on Wed Jul 05 22:47:38 UTC 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
MAJOR
METABOLIC ENZYME -> SUBSTRATE
MINOR
Related Record Type Details
METABOLITE ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY