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ACTIVE PHARMA INGREDIENTS

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Synopsis

ACTIVE PHARMA INGREDIENTS

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Chemistry

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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

Epalrestat

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 Formula	C₁₅H₁₃NO₃S₂
Molecular Weight	319.4 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	319.03368562 g/mol
Monoisotopic Mass	319.03368562 g/mol
Topological Polar Surface Area	115 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	519
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.)

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API Reference Price

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