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    Tolrestat

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    PharmaCompass
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    2D Structure
    Also known as: 82964-04-3, Alredase, Lorestat, Tolrestatin, Ay-27773, Tolrestatum
    Molecular Formula
    C16H14F3NO3S
    Molecular Weight
    357.3  g/mol
    InChI Key
    LUBHDINQXIHVLS-UHFFFAOYSA-N
    FDA UNII
    0T93LG5NMK
    Tolrestat (INN) (AY-27773) is an aldose reductase inhibitor which was approved for the control of certain diabetic complications. While it was approved for marketed in several countries, it failed a Phase III trial in the U.S. due to toxicity and never received FDA approval. It was sold under the tradename Alredase but was discontinued by Wyeth in 1997 because of the risk of severe liver toxicity and death.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[[6-methoxy-5-(trifluoromethyl)naphthalene-1-carbothioyl]-methylamino]acetic acid
    2.1.2 InChI
    InChI=1S/C16H14F3NO3S/c1-20(8-13(21)22)15(24)11-5-3-4-10-9(11)6-7-12(23-2)14(10)16(17,18)19/h3-7H,8H2,1-2H3,(H,21,22)
    2.1.3 InChI Key
    LUBHDINQXIHVLS-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN(CC(=O)O)C(=S)C1=CC=CC2=C1C=CC(=C2C(F)(F)F)OC
    2.2 Other Identifiers
    2.2.1 UNII
    0T93LG5NMK
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Ay 27773

    2. Ay-27,773

    3. N-((5-(trifluoromethyl)-6-methoxy-1-naphthalenyl)thioxomethyl)-n-methylglycine

    4. N-5-trifluoromethyl-6-methoxy-1-thionaphthoyl-n-methylglycine

    2.3.2 Depositor-Supplied Synonyms

    1. 82964-04-3

    2. Alredase

    3. Lorestat

    4. Tolrestatin

    5. Ay-27773

    6. Tolrestatum

    7. Ay-27,773

    8. Ay 27773

    9. 2-(6-methoxy-n-methyl-5-(trifluoromethyl)naphthalene-1-carbothioamido)acetic Acid

    10. Chembl436

    11. 0t93lg5nmk

    12. N-(6-methoxythio-5-(trifluoromethyl)-1-naphthoyl)sarcosine

    13. Chebi:48549

    14. N-{[6-methoxy-5-(trifluoromethyl)naphthalen-1-yl]carbonothioyl}-n-methylglycine

    15. 2-[[6-methoxy-5-(trifluoromethyl)naphthalene-1-carbothioyl]-methylamino]acetic Acid

    16. Ncgc00183862-01

    17. N-(6-methoxy-5-(trifluoromethyl)naphthalene-1-carbonothioyl)-n-methylglycine

    18. Glycine, N-((6-methoxy-5-(trifluoromethyl)-1-naphthalenyl)thioxomethyl)-n-methyl-

    19. Tolrestatum [latin]

    20. N-{[6-methoxy-5-(trifluoromethyl)-1-naphthyl]carbonothioyl}-n-methylglycine

    21. 2-{1-[6-methoxy-5-(trifluoromethyl)naphthalen-1-yl]-n-methylmethanethioamido}acetic Acid

    22. N-((6-methoxy-5-(trifluoromethyl)-1-naphthalenyl)thioxomethyl)-n-methylglycine

    23. N-[[6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]thioxomethyl]-n-methylglycine

    24. Tol

    25. Unii-0t93lg5nmk

    26. N-[6-methoxythio-5-(trifluoromethyl)-1-naphthoyl]sarcosine

    27. Alrestin

    28. Tolrestat [usan:inn:ban]

    29. Glycine, N-[[6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]thioxomethyl]-n-methyl-

    30. Alredase (tn)

    31. Tolrestat [inn]

    32. Tolrestat [mi]

    33. Tolrestat (usan/inn)

    34. Tolrestat [usan]

    35. Tolrestat [mart.]

    36. Tolrestat [who-dd]

    37. Dsstox_cid_28760

    38. Dsstox_rid_83029

    39. Dsstox_gsid_48834

    40. Schembl49326

    41. Gtpl7404

    42. Bdbm16314

    43. Dtxsid80904890

    44. Bcpp000039

    45. Bcp02377

    46. Zinc3780343

    47. Tox21_113316

    48. Akos005146007

    49. Cs-2040

    50. Db02383

    51. Vs-0127

    52. N-((6-methoxy-5-(trifluoromethyl)naphthalen-1-yl)thioxomethyl)-n-methylglycine

    53. Hy-16500

    54. Cas-75820-08-5

    55. Ft-0753651

    56. A13083

    57. C01621

    58. D02323

    59. 964t043

    60. J-522752

    61. Q7814620

    62. [([6-methoxy-5-(trifluoromethyl)-1-naphthyl]carbothioyl)(methyl)amino]acetic Acid #

    63. [(6-methoxy-5-trifluoromethyl-naphthalene-1-carbothioyl)-methyl-amino]-acetic Acid

    64. 2-{[6-methoxy-5-(trifluoromethyl)naphthalen-1-yl]-n-methylmethanethioamido}acetic Acid

    65. N-[[5-(trifluoromethyl)-6-methoxy-1-naphthalenyl]thioxomethyl]-n-methylglycine

    2.4 Create Date
    2005-03-28
    3 Chemical and Physical Properties
    Molecular Weight 357.3 g/mol
    Molecular Formula C16H14F3NO3S
    XLogP33.7
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count4
    Exact Mass357.06464897 g/mol
    Monoisotopic Mass357.06464897 g/mol
    Topological Polar Surface Area81.9 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity486
    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 pharmacological control of certain diabetic complications.

    5 Pharmacology and Biochemistry
    5.1 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.)

    5.2 ATC Code

    A - Alimentary tract and metabolism

    A10 - Drugs used in diabetes

    A10X - Other drugs used in diabetes

    A10XA - Aldose reductase inhibitors

    A10XA01 - Tolrestat