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    Enoximone

    FINISHED DOSAGE FORMULATIONS

    GLOBAL SALES INFORMATION

    PharmaCompass
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    2D Structure
    Also known as: 77671-31-9, Perfan, Fenoximone, Mdl-17043, Mdl 17,043, 4-methyl-5-(4-methylsulfanylbenzoyl)-1,3-dihydroimidazol-2-one
    Molecular Formula
    C12H12N2O2S
    Molecular Weight
    248.30  g/mol
    InChI Key
    ZJKNESGOIKRXQY-UHFFFAOYSA-N
    FDA UNII
    C7Z4ITI7L7
    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.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-methyl-5-(4-methylsulfanylbenzoyl)-1,3-dihydroimidazol-2-one
    2.1.2 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)
    2.1.3 InChI Key
    ZJKNESGOIKRXQY-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=C(NC(=O)N1)C(=O)C2=CC=C(C=C2)SC
    2.2 Other Identifiers
    2.2.1 UNII
    C7Z4ITI7L7
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Fenoximone

    2. Mdl 17,043

    3. Mdl 17043

    4. Mdl 19,438

    5. Mdl 19438

    6. Mdl-17,043

    7. Mdl-17043

    8. Mdl-19,438

    9. Mdl17,043

    10. Mdl17043

    11. Mdl19,438

    12. Perfan

    2.3.2 Depositor-Supplied Synonyms

    1. 77671-31-9

    2. Perfan

    3. Fenoximone

    4. Mdl-17043

    5. Mdl 17,043

    6. 4-methyl-5-(4-methylsulfanylbenzoyl)-1,3-dihydroimidazol-2-one

    7. 4-methyl-5-(p-(methylthio)benzoyl)-4-imidazolin-2-one

    8. Rmi-17043

    9. 2h-imidazol-2-one, 1,3-dihydro-4-methyl-5-(4-(methylthio)benzoyl)-

    10. C7z4iti7l7

    11. Chembl249856

    12. Enoximonum [latin]

    13. Ncgc00015400-02

    14. Enoximona [spanish]

    15. Enoximona

    16. Enoximonum

    17. 1,3-dihydro-4-methyl-5-[4-(methylthio)benzoyl]-2h-imidazol-2-one

    18. 1,3-dihydro-4-methyl-5-[4-methylthiobenzoyl]-2h-imidazol-2-one

    19. Dsstox_cid_25147

    20. Dsstox_rid_80702

    21. Dsstox_gsid_45147

    22. Perfane

    23. 2h-imidazol-2-one, 1,3-dihydro-4-methyl-5-[4-(methylthio)benzoyl]-

    24. Smr000857318

    25. Mdl-17,043

    26. Cas-77671-31-9

    27. Perfan (tn)

    28. Enoximone (usan/inn)

    29. Unii-c7z4iti7l7

    30. Enoximone [usan:inn:ban]

    31. Enoximone, Solid

    32. Enoximone [inn]

    33. Enoximone [jan]

    34. Enoximone [mi]

    35. Enoximone [usan]

    36. Lopac-e-1279

    37. Enoximone [mart.]

    38. E 1279

    39. Enoximone [who-dd]

    40. Lopac0_000410

    41. Schembl44049

    42. Mls001335963

    43. Mls001335964

    44. Mls002172494

    45. Gtpl9063

    46. Schembl5702510

    47. Dtxsid8045147

    48. Chebi:135010

    49. Hms2234c20

    50. Hms3261a22

    51. Hms3369o01

    52. Bcp04265

    53. Ex-a3632

    54. Hy-b1639

    55. Zinc9225358

    56. Tox21_110137

    57. Tox21_500410

    58. Bdbm50241379

    59. Akos005145769

    60. Tox21_110137_1

    61. Ac-3396

    62. Ccg-204503

    63. Db04880

    64. Lp00410

    65. Sdccgsbi-0050396.p002

    66. Ncgc00015400-01

    67. Ncgc00015400-03

    68. Ncgc00015400-04

    69. Ncgc00015400-05

    70. Ncgc00015400-10

    71. Ncgc00093835-01

    72. Ncgc00093835-02

    73. Ncgc00261095-01

    74. As-81876

    75. Db-056240

    76. B6833

    77. Cs-0013589

    78. E1370

    79. Eu-0100410

    80. Ft-0630855

    81. D04004

    82. 671e319

    83. A848234

    84. Sr-01000075850

    85. Q5379471

    86. Sr-01000075850-1

    87. 4-methyl-5-(4-(methylthio)benzoyl)-1h-imidazol-2(3h)-one

    88. 5-methyl-4-(4-(methylthio)benzoyl)-1h-imidazol-2(3h)-one

    89. 4-methyl-5-(4-methylsulfanyl-benzoyl)-1,3-dihydro-imidazol-2-one

    90. 4-methyl-5-[4-(methylsulfanyl)benzoyl]-1,3-dihydro-2h-imidazol-2-one

    91. 4-methyl-5-[4-(methylsulfanyl)benzoyl]-2,3-dihydro-1h-imidazol-2-one

    92. (enoximone)4-methyl-5-(4-methylsulfanyl-benzoyl)-1,3-dihydro-imidazol-2-one

    93. 4-methyl-5-(4-methylsulfanyl-benzoyl)-1,3-dihydro-imidazol-2-one (enoximone)

    94. 4-methyl-5-(4-methylsulfanyl-benzoyl)-1,3-dihydro-imidazol-2-one(enoximone)

    95. 4-methyl-5-(4-methylsulfanyl-benzoyl)-1,3-dihydro-imidazol-2-one(fenoximone, Mdl-17043)

    96. 4-methyl-5-{[4-(methylsulfanyl)phenyl]carbonyl}-2,3-dihydro-1h-imidazol-2-one

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 248.30 g/mol
    Molecular Formula C12H12N2O2S
    XLogP31.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count3
    Exact Mass248.06194880 g/mol
    Monoisotopic Mass248.06194880 g/mol
    Topological Polar Surface Area83.5 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity371
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of congestive heart failure.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    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.

    5.2 MeSH Pharmacological Classification

    Cardiotonic Agents

    Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE). (See all compounds classified as Cardiotonic Agents.)

    Phosphodiesterase 3 Inhibitors

    Compounds that specifically inhibit PHOSPHODIESTERASE 3. (See all compounds classified as Phosphodiesterase 3 Inhibitors.)

    Vasodilator Agents

    Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

    5.3 ATC Code

    C - Cardiovascular system

    C01 - Cardiac therapy

    C01C - Cardiac stimulants excl. cardiac glycosides

    C01CE - Phosphodiesterase inhibitors

    C01CE03 - Enoximone

    5.4 Absorption, Distribution and Excretion

    Absorption

    Bioavailabvility is 50% following oral administration.

    5.5 Metabolism/Metabolites

    Hepatic oxidation

    5.6 Biological Half-Life

    4-10 hours

    5.7 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.