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    Epalrestat

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    REF. STANDARDS & IMPURITIES

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    2D Structure
    Also known as: 82159-09-9, Kinedak, Epalrestatum, Epalrestat [inn], Ono 2235, Ono-2235
    Molecular Formula
    C15H13NO3S2
    Molecular Weight
    319.4  g/mol
    InChI Key
    CHNUOJQWGUIOLD-NFZZJPOKSA-N
    FDA UNII
    424DV0807X
    Epalrestat is an orally available, a non-competitive, reversible inhibitor of aldose reductase (AR), with potential antineoplastic, antioxidant, and anti-inflammatory activities. Upon oral administration, epalrestat non-competitively binds to AR, a polyol pathway enzyme that catalyzes reactive oxygen species (ROS)-initiated lipid peroxidation-generated lipid aldehydes and their glutathione conjugates, which have been implicated in the activation of transcription factors such as nuclear factor kappa-light-chain-enhancer of activated B cells (NF-kappa B) and activator protein-1 (AP-1), which control the transcription of many inflammatory cytokines. Increased inflammatory cytokines and growth factors promote cell proliferation, a primary feature in the tumorigenesis process. AR is overexpressed in several oxidative stress- and inflammation-related conditions, including cancer.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[(5Z)-5-[(E)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
    2.1.2 InChI
    InChI=1S/C15H13NO3S2/c1-10(7-11-5-3-2-4-6-11)8-12-14(19)16(9-13(17)18)15(20)21-12/h2-8H,9H2,1H3,(H,17,18)/b10-7+,12-8-
    2.1.3 InChI Key
    CHNUOJQWGUIOLD-NFZZJPOKSA-N
    2.1.4 Canonical SMILES
    CC(=CC1=CC=CC=C1)C=C2C(=O)N(C(=S)S2)CC(=O)O
    2.1.5 Isomeric SMILES
    C/C(=C\C1=CC=CC=C1)/C=C\2/C(=O)N(C(=S)S2)CC(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    424DV0807X
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3-carboxymethyl-5-(methyl-3-phenylpropenylidene)rhodanine

    2. Ono 2

    3. Ono 2235

    4. Ono-2

    5. Ono-2235

    2.3.2 Depositor-Supplied Synonyms

    1. 82159-09-9

    2. Kinedak

    3. Epalrestatum

    4. Epalrestat [inn]

    5. Ono 2235

    6. Ono-2235

    7. Ono-2

    8. 2-((z)-5-((e)-2-methyl-3-phenylallylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic Acid

    9. Aldonil

    10. Aldorin

    11. Tanglin

    12. 2-[(5z)-5-[(e)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic Acid

    13. Chembl56337

    14. 5-((1z,2e)-2-methyl-3-phenylpropenylidene)-4-oxo-2-thioxo-3-thiazolidineacetic Acid

    15. Chebi:31539

    16. Ono2235

    17. 5-((z,e)-beta-methylcinnamylidene)-4-oxo-2-thioxo-3-thiazolidineacetic Acid

    18. Mfcd00865484

    19. 424dv0807x

    20. {(5z)-5-[(2e)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}acetic Acid

    21. Epalrestatum [latin]

    22. {5-[(e)-2-methyl-3-phenyl-prop-2-en-(z)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-acetic Acid

    23. 2-[(5z)-5-[(2e)-2-methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic Acid

    24. Ono 2

    25. Kinedak (tn)

    26. Unii-424dv0807x

    27. Ncgc00164613-01

    28. Epalrestat- Bio-x

    29. 5-[(1z, 2e)-2-methyl-3-phenylpropenylidene]-4-oxo2-thioxo-3-thiazolidineacetic Acid

    30. Epalrestat [mi]

    31. Epalrestat [jan]

    32. Epalrestat (jp17/inn)

    33. Epalrestat [mart.]

    34. 3-thiazolidineacetic Acid, 5-(2-methyl-3-phenyl-2-propenylidene)-4-oxo-2-thioxo-, (e,e)-

    35. Epalrestat [who-dd]

    36. Schembl49049

    37. Mls000806985

    38. Dtxsid1046479

    39. Gtpl11371

    40. Regid_for_cid_1549120

    41. Hms2747m09

    42. Hms3887a17

    43. Zinc1533688

    44. Bbl029067

    45. Bdbm50049730

    46. S2035

    47. Stk337187

    48. Akos000274207

    49. Bcp9000649

    50. Ccg-267693

    51. Db15293

    52. Ncgc00164613-08

    53. Ncgc00164613-12

    54. As-13345

    55. Be164412

    56. Hy-66009

    57. Smr000414799

    58. Bcp0726000053

    59. E0906

    60. Sw219826-1

    61. D01688

    62. Ab00647195_06

    63. 159e099

    64. Q5382029

    65. [5-(2-methyl-3-phenyl-allylidene)-4-oxo-2-thioxo-thiazolidin-3-yl]-acetic Acid

    66. 2-(5-(2-methyl-3-phenylallylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetic Acid

    67. 5-((z,e)-.beta.-methylcinnamylidene)-4-oxo-2-thioxo-3-thiazolidineacetic Acid

    68. (5-[(e)-2-methyl-3-phenyl-prop-2-en-(z)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-yl)-acetic Acid 82159-

    69. {(5z)-5-[(2e)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}acetic Acid

    70. 2-[(5z)-5-[(e)-3-phenil-2-methylprop-2-enylidene]-4-oxo-2-thioxo-3-thiazolidinyl]acetic Acid

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 319.4 g/mol
    Molecular Formula C15H13NO3S2
    XLogP33.8
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count4
    Exact Mass319.03368562 g/mol
    Monoisotopic Mass319.03368562 g/mol
    Topological Polar Surface Area115 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity519
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count2
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)