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    dextrosimendan

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    2D Structure
    Also known as: 141505-33-1, Simdax, (r)-simendan, (-)-or-1259, Or-1259, Simendan, (r)-
    Molecular Formula
    C14H12N6O
    Molecular Weight
    280.28  g/mol
    InChI Key
    WHXMKTBCFHIYNQ-SECBINFHSA-N
    FDA UNII
    C6T4514L4E
    A hydrazone and pyridazine derivative; the levo-form is a phosphodiesterase III inhibitor, calcium-sensitizing agent, and inotropic agent that is used in the treatment of HEART FAILURE.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[[4-[(4R)-4-methyl-6-oxo-4,5-dihydro-1H-pyridazin-3-yl]phenyl]hydrazinylidene]propanedinitrile
    2.1.2 InChI
    InChI=1S/C14H12N6O/c1-9-6-13(21)19-20-14(9)10-2-4-11(5-3-10)17-18-12(7-15)8-16/h2-5,9,17H,6H2,1H3,(H,19,21)/t9-/m1/s1
    2.1.3 InChI Key
    WHXMKTBCFHIYNQ-SECBINFHSA-N
    2.1.4 Canonical SMILES
    CC1CC(=O)NN=C1C2=CC=C(C=C2)NN=C(C#N)C#N
    2.1.5 Isomeric SMILES
    C[C@@H]1CC(=O)NN=C1C2=CC=C(C=C2)NN=C(C#N)C#N
    2.2 Other Identifiers
    2.2.1 UNII
    C6T4514L4E
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. ((4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazono)propanedinitrile

    2. Dextrosimendan

    3. Or 1259

    4. Or 1855

    5. Or-1259

    6. Or-1855

    7. Simadax

    8. Simendan

    2.3.2 Depositor-Supplied Synonyms

    1. 141505-33-1

    2. Simdax

    3. (r)-simendan

    4. (-)-or-1259

    5. Or-1259

    6. Simendan, (r)-

    7. Chebi:50567

    8. 2-[[4-[(4r)-4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl]phenyl]hydrazinylidene]propanedinitrile

    9. Nsc-759644

    10. Levosimedan

    11. C6t4514l4e

    12. Or1259

    13. (r)-((4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazono) Propanedintrile

    14. (r)-n-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)carbonohydrazonoyl Dicyanide

    15. Levosimendan [inn]

    16. Dsstox_cid_26445

    17. Dsstox_rid_81620

    18. Mesoxalonitrile (p-((r)-1,4,5,6-tetrahydro-4-methyl-6-oxo-pyridazinyl)phenyl)hydrazone

    19. Dsstox_gsid_46445

    20. Levosimendanum

    21. Smr002529692

    22. Simdax (tn)

    23. Cas-141505-33-1

    24. Levosimendan (usan/inn)

    25. Levosimendan [usan:inn]

    26. Or 1259

    27. Unii-c6t4514l4e

    28. ((4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazono)propanedinitrile

    29. Levosimendan- Bio-x

    30. Levosimendan [mi]

    31. Levosimendan [usan]

    32. Mesoxalonitrile (-)-(p((r)-1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazone

    33. Schembl83243

    34. Levosimendan [mart.]

    35. Mls003899227

    36. Mls006010741

    37. Levosimendan [who-dd]

    38. Chembl2051955

    39. Dtxsid9046445

    40. Levosimendan, >=98% (hplc)

    41. Hms3264g03

    42. Hms3884n17

    43. Kuc109648n

    44. Pharmakon1600-01502356

    45. Act02710

    46. Bcp07048

    47. Zinc3915645

    48. Tox21_112191

    49. Tox21_113768

    50. Bdbm50469700

    51. Mfcd00867135

    52. Nsc759644

    53. S2446

    54. Akos015895214

    55. Tox21_112191_1

    56. Ac-1752

    57. Am84381

    58. Ccg-213048

    59. Db00922

    60. Ds-8918

    61. Nsc 759644

    62. ({4-[(4r)-4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl]phenyl}hydrazono)propanedintrile

    63. 2-[[4-[(4r)-4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl]phenyl]hydrazono]propanedinitrile

    64. Ksc-210-010

    65. Ncgc00253641-01

    66. Ncgc00263564-01

    67. Ncgc00263564-02

    68. Bm164625

    69. Hy-14286

    70. L0320

    71. Sw219172-1

    72. A11874

    73. D04720

    74. N12889

    75. Ab01562970_01

    76. Ab01562970_02

    77. 741l087

    78. A807767

    79. Q162541

    80. Sr-01000931342

    81. Sr-01000931342-2

    82. 1-beta-d-ribofuranose-1h-1,2,4-triazole-3-methylcarbonate

    83. (r)-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)carbonohydrazonoyl Dicyanide

    84. (r)-n-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)carbonohydrazonoyldicyanide

    85. 1-cyano-n-{4-[(4r)-4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl]phenyl}methanecarbohydrazonoyl Cyanide

    86. 2-(2-(4-((4r)-1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazinylidene)propanedinitrile

    87. Mesoxalonitrile (-)-(p((r)-1,4,5,6-tetrahydro-4-methyl-6- Oxo-3-pyridazinyl)phenyl)hydrazone

    88. Propanedinitrile, ((4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazono)-, (r)-

    89. Propanedinitrile, 2-(2-(4-((4r)-1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl)hydrazinylidene)-

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 280.28 g/mol
    Molecular Formula C14H12N6O
    XLogP32.3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count3
    Exact Mass280.10725903 g/mol
    Monoisotopic Mass280.10725903 g/mol
    Topological Polar Surface Area113 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity549
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    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 short term treatment of acutely decompensated severe chronic heart failure (CHF). Also being investigated for use/treatment in heart disease.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Levosimendan is a new Ca2+-sensitizing inotropic agent. Ca2+ sensitizers represent a new class of inotropic agents, which overcome the disadvantages associated with currently available inotropic agents in as they are not associated with an increased risk of arrhythmias, cell injury and death due to Ca2+ overload in myocardial cells; they do not increase the activation energy; and they have the potential to reverse contractile dysfunction under pathophysiologic conditions, such as acidosis or myocardial stunning. Levosimendan has not been approved for use in the U.S. or Canada.

    5.2 MeSH Pharmacological Classification

    Vasodilator Agents

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

    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.)

    5.3 ATC Code

    C - Cardiovascular system

    C01 - Cardiac therapy

    C01C - Cardiac stimulants excl. cardiac glycosides

    C01CX - Other cardiac stimulants

    C01CX08 - Levosimendan

    5.4 Absorption, Distribution and Excretion

    Absorption

    The bioavailability of oral levosimendan is 85 ± 6% in healthy volunteers and 84 ± 4% in patients.

    5.5 Metabolism/Metabolites

    Complete metabolism, with some active metabolites (OR-1855 and OR-1896) possibly extending the drug's haemodynamic effects.

    5.6 Biological Half-Life

    Eliminination half-life is approximately 1 hour.

    5.7 Mechanism of Action

    Levosimendan appears to increase myofilament calcium sensitivity by binding to cardiac troponin C in a calcium-dependent manner. This stabilizes the calcium-induced conformational change of troponin C, thereby (1) changing actin-myosin cross-bridge kinetics apparently without increasing the cycling rate of the cross-bridges or myocardial ATP consumption, (2) increasing the effects of calcium on cardiac myofilaments during systole and (3) improving contraction at low energy cost (inotropic effect). Calcium concentration and, therefore, sensitization decline during diastole, allowing normal or improved diastolic relaxation. Levosimendan also leads to vasodilation through the opening of ATP-sensitive potassium channels. By these inotropic and vasodilatory actions, levosimendan increases cardiac output without increasing myocardial oxygen demand. Levosimendan also has a selective phosphodiesterase (PDE)-III inhibitory action that may contribute to the inotropic effect of this compound under certain experimental conditions. It has been reported that levosimendan may act preferentially as a Ca2+ sensitizer at lower concentrations, whereas at higher concentrations its action as a PDE-III inhibitor becomes more prominent in experimental animals and humans.