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.
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- Contraindications & Blackbox Warnings
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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 A 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
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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. Isosorbide mononitrate Enoximone may increase the vasodilatory activities of Isosorbide mononitrate. Milrinone The risk or severity of congestive heart failure, bleeding, hypotension, and Tachycardia can be increased when Milrinone is combined with Enoximone. Patent Blue The therapeutic efficacy of Enoximone can be decreased when used in combination with Patent Blue. Riociguat Enoximone may increase the hypotensive activities of Riociguat. 
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- 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
Phase Status Purpose Conditions Count 4 Terminated Treatment Enoximone / Exacerbation of COPD / Phosphodiesterase Inhibitor 1 4 Unknown Status Treatment Microcirculation / Severe Sepsis 1 3 Completed Treatment Coronary Artery Disease (CAD) 1 3 Terminated Treatment Congestive Heart Failure (CHF) 2
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
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-004i-3910100000-ff2ed6a9d4b5b2530185
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes.
- Gene Name
- PDE3A
- Uniprot ID
- Q14432
- Uniprot Name
- cGMP-inhibited 3',5'-cyclic phosphodiesterase A
- 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]
Drug created at October 20, 2007 19:43 / Updated at June 19, 2021 00:26