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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

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 ( + / - )

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
A case of severe hypoglycemia due to pimobendan.
2001 Aug
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
Effect of pimobendan in patients with chronic heart failure.
2001 Winter
Normalization of left ventricular parameters following combined pimobendan and carvedilol treatment in a case of unclassified cardiomyopathy with longstanding refractory status.
2002 Dec
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
A double-blind, randomized, placebo-controlled study of pimobendan in dogs with dilated cardiomyopathy.
2002 May-Jun
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
[Inotropic agents].
2003 May
[Roles of cytokines in the pathogenesis of heart failure].
2003 May
Treatment of congestive heart failure.
2003 Nov
[If the myofilaments become sensitive: Ca2+-sensitizer for the therapy of heart insufficiency].
2005 Apr 15
[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
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
[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
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 Sat Jun 26 12:40:43 UTC 2021
Edited
by admin
on Sat Jun 26 12:40:43 UTC 2021
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 [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
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