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Enoximone

July 24, 2017
Common Name

Enoximone Description

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. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source PerfanKegg Aventis brand OF enoximoneMeSH Enoximone aventis brandMeSH FenoximoneMeSH Enoximone myogen brandMeSH Myogen brand OF enoximoneMeSH Carinopharm brand OF enoximoneMeSH Enoximone carinopharm brandMeSH

Chemical Formlia

C12H12N2O2S Average Molecliar Weight

248.301 Monoisotopic Molecliar Weight

248.061948328 IUPAC Name

4-methyl-5-[4-(methylslifanyl)benzoyl]-2,3-dihydro-1H-imidazol-2-one Traditional Name

enoximone CAS Registry Number

77671-31-9 SMILES

CSC1=CC=C(C=C1)C(=O)C1=C(C)NC(=O)N1

InChI Identifier

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)

InChI Key

ZJKNESGOIKRXQY-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic oxygen compounds Sub Class

Organooxygen compounds Direct Parent

Aryl-phenylketones Alternative Parents

  • Thiophenol ethers
  • Benzoyl derivatives
  • Carbonylimidazoles
  • Alkylarylthioethers
  • Vinylogous amides
  • Heteroaromatic compounds
  • Ureas
  • Slifenyl compounds
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Aryl-phenylketone
  • Aryl thioether
  • Benzoyl
  • Thiophenol ether
  • Imidazole-4-carbonyl group
  • Alkylarylthioether
  • Monocyclic benzene moiety
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Vinylogous amide
  • Urea
  • Slifenyl compound
  • Organoheterocyclic compound
  • Thioether
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organoslifur compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Cardiotonic Agents
  • Phosphodiesterase Inhibitors
  • Vasodilator Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point256 °CNot Available Boiling PointNot AvailableNot Available Water Solubility6.82e-02 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.068 mg/mLALOGPS logP1.97ALOGPS logP1.84ChemAxon logS-3.6ALOGPS pKa (Strongest Acidic)9.68ChemAxon pKa (Strongest Basic)-7.8ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area58.2 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity70.05 m3·mol-1ChemAxon Polarizability25.67 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-004i-3910100000-ff2ed6a9d4b5b2530185View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04880

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04880

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB04880 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    48492 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Enoximone NuGOwiki Link

    HMDB15599 Metagene Link

    HMDB15599 METLIN ID

    Not Available PubChem Compound

    53708 PDB ID

    Not Available ChEBI ID

    521520

    Product: Doxorubicin

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. 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. [PubMed:17714066 ]
    2. 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. [PubMed:16987374 ]
    3. 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. [PubMed:17544886 ]
    4. 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. [PubMed:17696974 ]

    Enzymes

    General function:
    Involved in catalytic activity
    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 (By similarity).
    Gene Name:
    PDE3A
    Uniprot ID:
    Q14432
    Molecular weight:
    124978.06
    References
    1. 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. [PubMed:17714066 ]
    2. 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. [PubMed:16987374 ]

    PMID: 24426233

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