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Chemistry

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Also known as: Epidaza, 1616493-44-7, Hbi-8000, Cs-055, Cs055, 743438-44-0

Molecular Formula

C₂₂H₁₉FN₄O₂

Molecular Weight

390.4 g/mol

InChI Key

SZMJVTADHFNAIS-BJMVGYQFSA-N

FDA UNII

87CIC980Y0

Tucidinostat is an orally bioavailable benzamide-type inhibitor of histone deacetylase (HDAC) isoenzymes 1, 2, 3 and 10, with potential antineoplastic activity. Upon administration, tucidinostat binds to and inhibits HDACs, leading to an increase of acetylation levels of histone proteins. This agent also inhibits the expression of kinases in the PI3K/Akt and MAPK/Ras signaling pathways and may result in cell cycle arrest and the induction of tumor cell apoptosis. This may inhibit tumor cell proliferation in susceptible tumor cells. HDACs, a class of enzymes that deacetylate chromatin histone proteins, are upregulated in many tumor types and play key roles in gene expression. Compared to some other benzamide-type HDAC inhibitors, chidamide is more stable, more resistant to degradation and has a longer half-life.

1 2D Structure

Tucidinostat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-(2-amino-4-fluorophenyl)-4-[[[(E)-3-pyridin-3-ylprop-2-enoyl]amino]methyl]benzamide

2.1.2 InChI

InChI=1S/C22H19FN4O2/c23-18-8-9-20(19(24)12-18)27-22(29)17-6-3-16(4-7-17)14-26-21(28)10-5-15-2-1-11-25-13-15/h1-13H,14,24H2,(H,26,28)(H,27,29)/b10-5+

2.1.3 InChI Key

SZMJVTADHFNAIS-BJMVGYQFSA-N

2.1.4 Canonical SMILES

C1=CC(=CN=C1)C=CC(=O)NCC2=CC=C(C=C2)C(=O)NC3=C(C=C(C=C3)F)N

2.1.5 Isomeric SMILES

C1=CC(=CN=C1)/C=C/C(=O)NCC2=CC=C(C=C2)C(=O)NC3=C(C=C(C=C3)F)N

2.2 Other Identifiers

2.2.1 UNII

87CIC980Y0

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (e)-n-(2-amino-4-fluorophenyl)-4-((3-(pyridin-3-yl)acrylamido)methyl)benzamide

2. Hbi-8000

2.3.2 Depositor-Supplied Synonyms

1. Epidaza

2. 1616493-44-7

3. Hbi-8000

4. Cs-055

5. Cs055

6. 743438-44-0

7. (e)-n-(2-amino-4-fluorophenyl)-4-((3-(pyridin-3-yl)acrylamido)methyl)benzamide

8. De-5-fluoro 4-fluorochidamide

9. Tucidinostat [usan]

10. Chidamide [who-dd]

11. 87cic980y0

12. Cs 055

13. N-(2-amino-4-fluorophenyl)-4-[[[(e)-3-pyridin-3-ylprop-2-enoyl]amino]methyl]benzamide

14. N-(2-amino-4-fluorophenyl)-4-(((1-oxo-3-(3-pyridinyl)-2-propen-1-yl)amino)methyl)benzamide

15. Benzamide, N-(2-amino-4-fluorophenyl)-4-((((2e)-1-oxo-3-(3-pyridinyl)-2-propen-1-yl)amino)methyl)-

16. Benzamide, N-(2-amino-4-fluorophenyl)-4-(((1-oxo-3-(3-pyridinyl)-2-propen-1-yl)amino)methyl)-

17. Tucidinostat Hcl

18. Epidaza In China

19. Epidaza (tn)

20. Tucidinostat [inn]

21. Tucidinostat [jan]

22. Tucidinostat [who-dd]

23. Unii-87cic980y0

24. Tucidinostat (jan/usan/inn)

25. Chembl3621988

26. Schembl13815849

27. Chebi:135918

28. Dtxsid701032295

29. Ex-a3245

30. Bdbm50457079

31. Db06334

32. Chidamide; Hbi-8000; Cs-055 Hcl

33. Bs-15501

34. Hy-109015

35. Cs-0030513

36. A51185

37. D10993

38. A899933

39. Q19903814

40. Benzamide, N-(2-amino-4-fluorophenyl)-4-(((1-oxo-3-(3-pyridinyl)-2-propen-1-yl)amino)methyl)-benzamide, N-(2-amino-4-fluorophenyl)-4-((((2e)-1-oxo-3-(3-pyridinyl)-2-propen-1-yl)amino)methyl)-

41. N-(2-amino-4-fluorophenyl)-4-(((2e)-3-(pyridin-3-yl)prop- 2-enamido)methyl)benzamide

42. N-(2-amino-4-fluorophenyl)-4-{(3-(pyridin-3-yl)prop-2-enamido)methyl}benzamide N-(2-amino-4-fluorophenyl)-4-{((2e)-3-(pyridin-3-yl)prop-2-enamido)methyl}benzamide

2.4 Create Date

2007-02-07

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₁₉FN₄O₂
Molecular Weight	390.4 g/mol
XLogP3	2.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Exact Mass	390.14920402 g/mol
Monoisotopic Mass	390.14920402 g/mol
Topological Polar Surface Area	97.1 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	577
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in cancer/tumors (unspecified).

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

Chidamide is an orally bioavailable histone deacetylase (HDAC) inhibitor derived from the benzamide class. Histone deacetylase inhibitors are a class of cancer drugs that induce selective regulation of gene expression in cancer cells. [HUYA Biosciences Press Release]

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