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Chemistry

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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
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 Weight 406.4 g/mol
Molecular Formula C20H17F3N2O4
XLogP33.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Exact Mass406.11404151 g/mol
Monoisotopic Mass406.11404151 g/mol
Topological Polar Surface Area70.1 Ų
Heavy Atom Count29
Formal Charge0
Complexity686
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

Investigated for use/treatment in prostate cancer.


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