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ACTIVE PHARMA INGREDIENTS

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Chemistry

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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

Tolrestat

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 Formula	C₁₆H₁₄F₃NO₃S
Molecular Weight	357.3 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	357.06464897 g/mol
Monoisotopic Mass	357.06464897 g/mol
Topological Polar Surface Area	81.9 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	486
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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

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