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

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
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
Increase in myofibrillar Ca2+ sensitivity induced by UD-CG 212 Cl, an active metabolite of pimobendan, in canine ventricular myocardium.
2001 Feb
New pharmacological strategies for the treatment of heart failure.
2001 Jul
Beneficial effects of the Ca2+ sensitizer EMD 57033 in exercising pigs with infarction-induced chronic left ventricular dysfunction.
2001 Oct
Decrease in Ca(2+)-sensitizing effect of UD-CG 212 Cl, a metabolite of pimobendan, under acidotic condition in canine ventricular myocardium.
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
Mechanisms of action of novel cardiotonic agents.
2002 Sep
Effects of rolipram, pimobendan and zaprinast on ischaemia-induced dysrhythmias and on ventricular cyclic nucleotide content in the anaesthetized rat.
2003 Mar
[Inotropic agents].
2003 May
[Roles of cytokines in the pathogenesis of heart failure].
2003 May
Treatment of congestive heart failure.
2003 Nov
The role of Ca++-sensitizers for the treatment of heart failure.
2003 Oct
Investigation of pimobendan versus benazepril in canine myxomatous valvular disease.
2003 Oct 4
Use of pimobendan in the management of heart failure.
2004 Sep
[If the myofilaments become sensitive: Ca2+-sensitizer for the therapy of heart insufficiency].
2005 Apr 15
Ca2+-sensitisers--a promising option to treat heart failure?
2005 Dec
[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
Effect of pimobendan on cardiopulmonary baroreflex control of sympathetic nerve activity in healthy young men.
2005 Oct 30
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
Pimobendan in heart failure therapy--a silver bullet?
2006 Mar-Apr
[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
Acute heart failure: inotropic agents and their clinical uses.
2006 Nov
Effects of pimobendan for mitral valve regurgitation in dogs.
2007 Apr
Treatment options in myocarditis: what we know from experimental data and how it translates to clinical trials.
2007 Sep
The value added by measuring myocardial contractility 'in vivo' in safety pharmacological profiling of drug candidates.
2007 Sep-Oct
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
Validity, reliability, and responsiveness of the Kansas City Cardiomyopathy Questionnaire in anemic heart failure patients.
2008 Mar
Agents with inotropic properties for the management of acute heart failure syndromes. Traditional agents and beyond.
2009 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
Synthesis of new 4,5-3(2H)pyridazinone derivatives and their cardiotonic, hypotensive, and platelet aggregation inhibition activities.
2010 Jan
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).
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