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

Details

Stereochemistry ACHIRAL
Molecular Formula C12H12N2O2S
Molecular Weight 248.301
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENOXIMONE

SMILES

CSC1=CC=C(C=C1)C(=O)C2=C(C)NC(=O)N2

InChI

InChIKey=ZJKNESGOIKRXQY-UHFFFAOYSA-N
InChI=1S/C12H12N2O2S/c1-7-10(14-12(16)13-7)11(15)8-3-5-9(17-2)6-4-8/h3-6H,1-2H3,(H2,13,14,16)

HIDE SMILES / InChI

Molecular Formula C12H12N2O2S
Molecular Weight 248.301
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Enoximone is an inhibitor of PDE3, which is used for the treatment of congestive heart failure. Also enoximone was shown to inhibit PDH in cardiac myocytes. The inhibition was shown to occur secondary to stimulating fatty acid oxidation

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.9 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PERFAN

Approved Use

PERFAN Injection is indicated for the treatment of congestive heart failure, typically where cardiac output is reduced and filling pressures increased, in patients who require intravenous therapy and who can be closely monitored.
PubMed

PubMed

TitleDatePubMed
[Vasodilatation and positive inotropic effect of the phosphodiesterase inhibitor enoximone].
1991
[Use of a new inotropic agent, enoximone, in heart surgery].
1991 Mar-Apr
Clinical pharmacology of intravenous enoximone: pharmacodynamics and pharmacokinetics in patients with heart failure.
1991 Sep
New strategies to control the inflammatory response in cardiac surgery.
2004 Feb
Bench-to-bedside review: hyperinsulinaemia/euglycaemia therapy in the management of overdose of calcium-channel blockers.
2006
Arginine-vasopressin in catecholamine-refractory septic versus non-septic shock in extremely low birth weight infants with acute renal injury.
2006
Enoximone in cardiac arrest caused by propranolol: two case reports.
2006 Jul
Intraaortic balloon pumping during cardioplegic arrest preserves lung function in patients with chronic obstructive pulmonary disease.
2006 Jul
Effect of combining phosphodiesterase III inhibitors with St Thomas Hospital's solution used as transplantation preservative solution in isolated rat hearts.
2006 Jun
A comparison of three phosphodiesterase type III inhibitors on mechanical and metabolic function in guinea pig isolated hearts.
2006 Jun
Acute heart failure: inotropic agents and their clinical uses.
2006 Nov
The metabolic and renal effects of adrenaline and milrinone in patients with myocardial dysfunction after coronary artery bypass grafting.
2007
Factors influencing the outcome of paediatric cardiac surgical patients during extracorporeal circulatory support.
2007 Jan 11
Effects of preemptive enoximone on left ventricular diastolic function after valve replacement for aortic stenosis.
2007 Jun
Current practice of hemodynamic monitoring and vasopressor and inotropic therapy in post-operative cardiac surgery patients in Germany: results from a postal survey.
2007 Mar
[Pleural effusion following coronary bypass surgery].
2007 Nov
Cardiovascular effects of enoximone in isoflurane anaesthetized ponies.
2007 Nov
Peripartum cardiomyopathy: review of the literature.
2007 Oct 31
[Potentialitis of phosphodiesterase inhibitors in management of patients with chronic heart failure complicating cardiac ischemia].
2008
ABCD of the phosphodiesterase family: interaction and differential activity in COPD.
2008
Understanding cardiac output.
2008
Recovery of heart function in children with acute severe heart failure.
2008 Apr 15
Levosimendan in cardiogenic shock: better than enoximone!
2008 Aug
Levosimendan is superior to enoximone in refractory cardiogenic shock complicating acute myocardial infarction.
2008 Aug
Effects of dobutamine on cardiovascular function and respiratory gas exchange after enoximone in isoflurane-anaesthetized ponies.
2008 Jul
[Continuous beta-block with esmolol in combination with enoximone: influence on cardiac function in high risk patients undergoing vascular surgery].
2008 Mar
Spontaneous perforation of the cystic duct in streptococcal toxic shock syndrome: a case report.
2008 Oct 29
Apart from the other members of PDE inhibitors' family, enoximone does not enhance renal ischemic reperfusion injury: the effects of enoximone on renal ischemia reperfusion.
2009
Agents with inotropic properties for the management of acute heart failure syndromes. Traditional agents and beyond.
2009 Dec
Inotropic therapy for heart failure: paradise lost.
2009 Dec
Effects of low-dose oral enoximone administration on mortality, morbidity, and exercise capacity in patients with advanced heart failure: the randomized, double-blind, placebo-controlled, parallel group ESSENTIAL trials.
2009 Dec
Vasodilators in the treatment of acute heart failure: what we know, what we don't.
2009 Dec
Inflammatory response to cardiopulmonary bypass with enoximone or steroids in patients undergoing myocardial revascularization: a preliminary report study.
2009 Feb
Is there a role for carvedilol in the management of pediatric heart failure? A meta analysis and e-mail survey of expert opinion.
2009 Jan
Masquerade: fulminant viral myocarditis mimicking a Q-wave anterolateral myocardial infarction.
2009 Jun
Influence of calcium chloride on the cardio-respiratory effects of a bolus of enoximone in isoflurane anaesthetized ponies.
2009 Mar
Levosimendan or enoximone in refractory cardiogenic shock?
2009 Mar
Evaluation of 30-day mortality of levosimendan versus enoximone.
2009 Mar
Comparison between lithium dilution and pulse contour analysis techniques for cardiac output measurement in isoflurane anaesthetized ponies: influence of different inotropic drugs.
2009 May
Long-term outcome of coronary artery bypass grafting in patients with left ventricular dysfunction.
2009 May
Influence of continuous perioperative beta-blockade in combination with phosphodiesterase inhibition on haemodynamics and myocardial ischaemia in high-risk vascular surgery patients.
2009 May
Cardiorespiratory effects of enoximone in anaesthetised colic horses.
2009 Nov
Left ventricular diastolic dysfunction of the cardiac surgery patient; a point of view for the cardiac surgeon and cardio-anesthesiologist.
2009 Nov 24
Levosimendan is superior to enoximone in refractory cardiogenic shock complicating acute myocardial infarction.
2009 Sep
Investigational positive inotropic agents for acute heart failure.
2009 Sep
Newer treatments for decompensated heart failure: focus on levosimendan.
2009 Sep 21
Enoxaparin, effective dosage for intensive care patients: double-blinded, randomised clinical trial.
2010
Weaning failure of cardiac origin: recent advances.
2010
Assessment of residual viability by enoximone echocardiography in patients with previous myocardial infarction correlation with positron emission tomographic studies and functional follow-up.
2010 May
Sildenafil attenuates pulmonary arterial pressure but does not improve oxygenation during ARDS.
2010 May
Patents

Patents

Sample Use Guides

Therapy should be initiated with a dose of 0.5-1.0 mg/kg given as a slow intravenous injection (not faster than 12.5 mg/min); further doses of 0.5 mg/kg may be given similarly every 30 min until a satisfactory response is achieved or a total initial dose of 3.0 mg/kg is reached. Alternatively treatment may be initiated as an infusion at a rate of 90 ug/kg/min administered over 10-30 min until the required haemodynamic response is achieved. To maintain the effects the initial dose (not more than 3.0 mg/kg) may be repeated as required every 3-6 h and adjusted according to the response of the patient. Alternatively, a continuous or intermittent infusion at a rate of 5-20 ug/kg/min may be instituted. The total dose over 24 h should not normally exceed 24.0 mg/kg.
Route of Administration: Intravenous
In Vitro Use Guide
Rat cardiac myocytes were incubated with 0.5 mM enoximone for 10 min at 37C and the effect of the drug on PDH activity was measured. Concentrations of 0.01, 0.05, 0.1, 0.25, 0.5 mM were used in assay, which was used to investigate the effect of enoximone on the oxidation of glucose and pyruvate.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:55:17 UTC 2023
Edited
by admin
on Sat Dec 16 17:55:17 UTC 2023
Record UNII
C7Z4ITI7L7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ENOXIMONE
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
PERFAN
Brand Name English
MDL-17043
Code English
Enoximone [WHO-DD]
Common Name English
2H-IMIDAZOL-2-ONE, 1,3-DIHYDRO-4-METHYL-5-(4-(METHYLTHIO)BENZOYL)-
Systematic Name English
enoximone [INN]
Common Name English
MDL 17,043
Code English
4-METHYL-5-(P-(METHYLTHIO)BENZOYL)-4-IMIDAZOLIN-2-ONE
Common Name English
ENOXIMONE [USAN]
Common Name English
ENOXIMONE [MI]
Common Name English
ENOXIMONE [MART.]
Common Name English
ENOXIMONE [JAN]
Common Name English
Classification Tree Code System Code
WHO-ATC C01CE03
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
NCI_THESAURUS C744
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
WHO-VATC QC01CE03
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C87375
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
DRUG BANK
DB04880
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
MERCK INDEX
m4913
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY Merck Index
DRUG CENTRAL
1014
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
INN
5582
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
CAS
77671-31-9
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
WIKIPEDIA
ENOXIMONE
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
USAN
U-83
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
ChEMBL
CHEMBL249856
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
PUBCHEM
53708
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
RXCUI
49626
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY RxNorm
SMS_ID
100000080255
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
EPA CompTox
DTXSID8045147
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
FDA UNII
C7Z4ITI7L7
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
EVMPD
SUB06542MIG
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
MESH
D017335
Created by admin on Sat Dec 16 17:55:17 UTC 2023 , Edited by admin on Sat Dec 16 17:55:17 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY