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Also known as: 254964-60-8, Abr-215050, Tasquinimod [inn], 4-hydroxy-5-methoxy-n,1-dimethyl-2-oxo-n-[4-(trifluoromethyl)phenyl]quinoline-3-carboxamide, 4-hydroxy-5-methoxy-n,1-dimethyl-2-oxo-n-(4-(trifluoromethyl)-phenyl)-1,2-dihydroquinoline-3-carboxamide, 756u07kn1r

Molecular Formula

C₂₀H₁₇F₃N₂O₄

Molecular Weight

406.4 g/mol

InChI Key

ONDYALNGTUAJDX-UHFFFAOYSA-N

FDA UNII

756U07KN1R

Tasquinimod is a quinoline-3-carboxamide linomide analogue with antiangiogenic and potential antineoplastic activities. Tasquinimod has been shown to decrease blood vessel density but the exact mechanism of action is not known. This agent has also been shown to augment the antineoplastic effects of docetaxel and androgen ablation in a murine model of prostate cancer involving human prostate cancer xenografts.

1 2D Structure

Tasquinimod

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]quinoline-3-carboxamide

2.1.2 InChI

InChI=1S/C20H17F3N2O4/c1-24(12-9-7-11(8-10-12)20(21,22)23)18(27)16-17(26)15-13(25(2)19(16)28)5-4-6-14(15)29-3/h4-10,26H,1-3H3

2.1.3 InChI Key

ONDYALNGTUAJDX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1C2=C(C(=CC=C2)OC)C(=C(C1=O)C(=O)N(C)C3=CC=C(C=C3)C(F)(F)F)O

2.2 Other Identifiers

2.2.1 UNII

756U07KN1R

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-hydroxy-5-methoxy-n,1-dimethyl-2-oxo-n-((4-trifluoromethyl)phenyl)-1,2-dihydroquinoline-3-carboxamide

2. Abr-215050

2.3.2 Depositor-Supplied Synonyms

1. 254964-60-8

2. Abr-215050

3. Tasquinimod [inn]

4. 4-hydroxy-5-methoxy-n,1-dimethyl-2-oxo-n-[4-(trifluoromethyl)phenyl]quinoline-3-carboxamide

5. 4-hydroxy-5-methoxy-n,1-dimethyl-2-oxo-n-(4-(trifluoromethyl)-phenyl)-1,2-dihydroquinoline-3-carboxamide

6. 756u07kn1r

7. 4-hydroxy-5-methoxy-n,1-dimethyl-2-oxo-n-((4-trifluoromethyl)phenyl)-1,2-dihydroquinoline-3-carboxamide

8. 4-hydroxy-5-methoxy-n,1-dimethyl-2-oxo-n-(4-(trifluoromethyl)phenyl)-1,2-dihydroquinoline-3-carboxamide

9. Unii-756u07kn1r

10. Tasq

11. 4-hydroxy-5-methoxy-n,1-dimethyl-2-oxo-n-[4-(trifluoromethyl)phenyl]-1,2-dihydroquinoline-3-carboxamide

12. Tasquinimod [mi]

13. Tasquinimod [who-dd]

14. Tasquinimod(abr-215050)

15. Gtpl8098

16. Schembl4476895

17. Chembl2107784

18. Dtxsid90180183

19. Zinc602397

20. Bcp10352

21. Bdbm50565139

22. Mfcd18251454

23. S7617

24. Am84841

25. Ccg-268712

26. Cs-0898

27. Db05861

28. Sb16938

29. Ncgc00379032-04

30. Ac-32481

31. As-35208

32. Hy-10528

33. Ds-001403

34. A911276

35. Q7687612

36. 1,2-dihydro-4-hydroxy-5-methoxy-n,1-dimethyl-2-oxo-n-[4-(trifluoromethyl)phenyl]-3-quinolinecarboxamide

37. 4-hydroxy-5-methoxy-n-methyl-1-methyl-2-oxo-n-(4-trifluoromethylphenyl)-1,2-dihydroquinoline-3-carboxamide

38. 4-hydroxy-n-[4-(trifluoromethyl)phenyl]-5-methoxy-n,1-dimethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

39. N-methyl-n-(4-trifluoromethyl-phenyl)-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxamide

2.4 Create Date

2011-12-26

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₇F₃N₂O₄
Molecular Weight	406.4 g/mol
XLogP3	3.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Exact Mass	406.11404151 g/mol
Monoisotopic Mass	406.11404151 g/mol
Topological Polar Surface Area	70.1 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	686
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