Explore a selection of our essential drug information below, or:
Identification
- Summary
Enoximone is a selective phosphodiesterase inhibitor indicated in the short term treatment of congestive heart failure.
- Generic Name
- Enoximone
- DrugBank Accession Number
- DB04880
- Background
Enoximone is a selective phosphodiesterase inhibitor with vasodilating and positive inotropic activity that does not cause changes in myocardial oxygen consumption. It is used in patients with congestive heart failure. Trials were halted in the U.S., but the drug is used in various countries.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Enoximone (DB04880)
- Weight
- Average: 248.301
Monoisotopic: 248.061948328 - Chemical Formula
- C12H12N2O2S
- Synonyms
- Enoximona
- Enoximone
- Enoximonum
- External IDs
- MDL 17,043
- MDL-17043
Pharmacology
- Indication
For the treatment of congestive heart failure.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Congestive heart failure (chf) •••••••••••• •••••••••• •••••••••• •••••••• Treatment of Congestive heart failure (chf) •••••••••••• •••••••••• •••••••••• •••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Enoximone is a phosphodiesterase inhibitor (type III) that increases the force of contraction of the heart and dilates blood vessels. In June 2005, Myogen announced that they were discontinuing development of enoximone due to negative results. The drug is approved for use in the UK.
- Mechanism of action
Further research is required to determine accurately the mechanism of action of drugs with phosphodiesterase inhibitory activity, however, inhibition of PDE3 inhibits degredation of cGMP. This allows for increased NO release and vascular relaxation.
Target Actions Organism AcGMP-inhibited 3',5'-cyclic phosphodiesterase 3A inhibitorHumans - Absorption
Bioavailabvility is 50% following oral administration.
- Volume of distribution
Not Available
- Protein binding
85%
- Metabolism
Hepatic oxidation
- Route of elimination
Not Available
- Half-life
4-10 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAmrinone The risk or severity of congestive heart failure, bleeding, hypotension, and Tachycardia can be increased when Amrinone is combined with Enoximone. Anagrelide The risk or severity of congestive heart failure, bleeding, hypotension, and Tachycardia can be increased when Anagrelide is combined with Enoximone. Cilostazol The risk or severity of congestive heart failure, bleeding, hypotension, and Tachycardia can be increased when Cilostazol is combined with Enoximone. Iloprost Iloprost may increase the hypotensive activities of Enoximone. Isosorbide mononitrate Enoximone may increase the vasodilatory activities of Isosorbide mononitrate. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Perfan
Categories
- ATC Codes
- C01CE03 — Enoximone
- Drug Categories
- Cardiac Stimulants Excl. Cardiac Glycosides
- Cardiac Therapy
- Cardiotonic Agents
- Cardiovascular Agents
- Compounds used in a research, industrial, or household setting
- Drugs causing inadvertant photosensitivity
- Enzyme Inhibitors
- Imidazoles
- Phosphodiesterase 3 Inhibitors
- Phosphodiesterase Inhibitors
- Photosensitizing Agents
- Protective Agents
- Vasodilating Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbonyl compounds
- Direct Parent
- Aryl-phenylketones
- Alternative Parents
- Thiophenol ethers / Benzoyl derivatives / Carbonylimidazoles / Alkylarylthioethers / Vinylogous amides / Heteroaromatic compounds / Ureas / Sulfenyl compounds / Azacyclic compounds / Organopnictogen compounds show 3 more
- Substituents
- Alkylarylthioether / Aromatic heteromonocyclic compound / Aryl thioether / Aryl-phenylketone / Azacycle / Azole / Benzenoid / Benzoyl / Heteroaromatic compound / Hydrocarbon derivative show 14 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- C7Z4ITI7L7
- CAS number
- 77671-31-9
- InChI Key
- ZJKNESGOIKRXQY-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 4-methyl-5-[4-(methylsulfanyl)benzoyl]-2,3-dihydro-1H-imidazol-2-one
- SMILES
- CSC1=CC=C(C=C1)C(=O)C1=C(C)NC(=O)N1
References
- General References
- Sandroni C, Cavallaro F, Caricato A, Scapigliati A, Fenici P, Antonelli M: Enoximone in cardiac arrest caused by propranolol: two case reports. Acta Anaesthesiol Scand. 2006 Jul;50(6):759-61. [Article]
- van der Maaten JM, de Vries AJ, Rietman GW, Gallandat Huet RC, De Hert SG: Effects of preemptive enoximone on left ventricular diastolic function after valve replacement for aortic stenosis. J Cardiothorac Vasc Anesth. 2007 Jun;21(3):357-66. Epub 2006 May 4. [Article]
- Schauvliege S, Van den Eede A, Duchateau L, Gasthuys F: Cardiovascular effects of enoximone in isoflurane anaesthetized ponies. Vet Anaesth Analg. 2007 Nov;34(6):416-30. Epub 2007 Aug 13. [Article]
- Boldt J, Suttner S: Combined use of ultra-short acting beta-blocker esmolol and intravenous phosphodiesterase 3 inhibitor enoximone. Expert Opin Pharmacother. 2007 Sep;8(13):2135-47. [Article]
- External Links
- Human Metabolome Database
- HMDB0015599
- KEGG Drug
- D04004
- PubChem Compound
- 53708
- PubChem Substance
- 46505575
- ChemSpider
- 48492
- BindingDB
- 50241379
- 49626
- ChEBI
- 135010
- ChEMBL
- CHEMBL249856
- ZINC
- ZINC000009225358
- Therapeutic Targets Database
- DAP000611
- PharmGKB
- PA164768794
- Wikipedia
- Enoximone
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Terminated Treatment Enoximone / Exacerbation of COPD / Phosphodiesterase Inhibitor 1 somestatus stop reason just information to hide 4 Unknown Status Treatment Microcirculation / Severe Sepsis 1 somestatus stop reason just information to hide 3 Completed Treatment Coronary Artery Disease (CAD) 1 somestatus stop reason just information to hide 3 Terminated Treatment Congestive Heart Failure (CHF) 2 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution, concentrate Intravenous; Parenteral 100 MG/20ML Solution, concentrate Intravenous 125 mg Solution, concentrate Intravenous 50 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 256 dec °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.0682 mg/mL ALOGPS logP 1.97 ALOGPS logP 1.84 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 9.68 Chemaxon pKa (Strongest Basic) -7.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 58.2 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 70.04 m3·mol-1 Chemaxon Polarizability 25.67 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9659 Blood Brain Barrier + 0.77 Caco-2 permeable - 0.5178 P-glycoprotein substrate Non-substrate 0.6512 P-glycoprotein inhibitor I Non-inhibitor 0.9333 P-glycoprotein inhibitor II Non-inhibitor 0.992 Renal organic cation transporter Non-inhibitor 0.892 CYP450 2C9 substrate Non-substrate 0.6586 CYP450 2D6 substrate Non-substrate 0.7445 CYP450 3A4 substrate Non-substrate 0.6998 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9431 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Inhibitor 0.5842 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8173 Ames test Non AMES toxic 0.7916 Carcinogenicity Non-carcinogens 0.9418 Biodegradation Not ready biodegradable 0.9737 Rat acute toxicity 2.0807 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9554 hERG inhibition (predictor II) Non-inhibitor 0.8438
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 167.3236816 predictedDarkChem Lite v0.1.0 [M-H]- 167.9913816 predictedDarkChem Lite v0.1.0 [M-H]- 157.84827 predictedDeepCCS 1.0 (2019) [M+H]+ 168.8255816 predictedDarkChem Lite v0.1.0 [M+H]+ 168.6492816 predictedDarkChem Lite v0.1.0 [M+H]+ 160.20625 predictedDeepCCS 1.0 (2019) [M+Na]+ 167.7570816 predictedDarkChem Lite v0.1.0 [M+Na]+ 166.29942 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Cyclic nucleotide phosphodiesterase with specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes (PubMed:1315035, PubMed:25961942, PubMed:8155697, PubMed:8695850). Has also activity toward cUMP (PubMed:27975297). Independently of its catalytic activity it is part of an E2/17beta-estradiol-induced pro-apoptotic signaling pathway. E2 stabilizes the PDE3A/SLFN12 complex in the cytosol, promoting the dephosphorylation of SLFN12 and activating its pro-apoptotic ribosomal RNA/rRNA ribonuclease activity. This apoptotic pathway might be relevant in tissues with high concentration of E2 and be for instance involved in placenta remodeling (PubMed:31420216, PubMed:34707099)
- Specific Function
- 3',5'-cyclic-amp phosphodiesterase activity
- Gene Name
- PDE3A
- Uniprot ID
- Q14432
- Uniprot Name
- cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A
- Molecular Weight
- 124978.06 Da
References
- Boldt J, Suttner S: Combined use of ultra-short acting beta-blocker esmolol and intravenous phosphodiesterase 3 inhibitor enoximone. Expert Opin Pharmacother. 2007 Sep;8(13):2135-47. [Article]
- Sandroni C, Cavallaro F, Caricato A, Scapigliati A, Fenici P, Antonelli M: Enoximone in cardiac arrest caused by propranolol: two case reports. Acta Anaesthesiol Scand. 2006 Jul;50(6):759-61. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at October 20, 2007 19:43 / Updated at June 19, 2021 00:26