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Laquinimod

Laquinimod

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Also known as: 248281-84-7, 5-chloro-n-ethyl-4-hydroxy-1-methyl-2-oxo-n-phenyl-1,2-dihydroquinoline-3-carboxamide, Abr-215062, Abr 215062, Laquinimod [inn], Civentichem cv-4057

Molecular Formula

C₁₉H₁₇ClN₂O₃

Molecular Weight

356.8 g/mol

InChI Key

GKWPCEFFIHSJOE-UHFFFAOYSA-N

FDA UNII

908SY76S4G

Laquinimod is an immunomodulator developed by Active Biotech and produced by Teva Pharmaceutical Industries. It is currently under development in phase III trials for treatment of multiple sclerosis as an oral therapy, like fingolimod. It has been shown to reduce disease activity on magnetic resonance imaging and to be well tolerated orally.

1 2D Structure

Laquinimod

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenylquinoline-3-carboxamide

2.1.2 InChI

InChI=1S/C19H17ClN2O3/c1-3-22(12-8-5-4-6-9-12)19(25)16-17(23)15-13(20)10-7-11-14(15)21(2)18(16)24/h4-11,23H,3H2,1-2H3

2.1.3 InChI Key

GKWPCEFFIHSJOE-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCN(C1=CC=CC=C1)C(=O)C2=C(C3=C(C=CC=C3Cl)N(C2=O)C)O

2.2 Other Identifiers

2.2.1 UNII

908SY76S4G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Abr 215062

2. Abr-215062

3. Abr215062

2.3.2 Depositor-Supplied Synonyms

1. 248281-84-7

2. 5-chloro-n-ethyl-4-hydroxy-1-methyl-2-oxo-n-phenyl-1,2-dihydroquinoline-3-carboxamide

3. Abr-215062

4. Abr 215062

5. Laquinimod [inn]

6. Civentichem Cv-4057

7. Laquinimod (abr-215062)

8. Abr215062

9. Tv-5600 Free Acid

10. 908sy76s4g

11. Abr-215062 Free Acid

12. 5-chloro-n-ethyl-4-hydroxy-1-methyl-2-oxo-n-phenylquinoline-3-carboxamide

13. N-ethyl-n-phenyl-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoquinoline-3-carboxamide

14. Mfcd08689859

15. 5-chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic Acid Ethyl-phenyl-amide

16. 3-quinolinecarboxamide, 5-chloro-n-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-n-phenyl-

17. Smr004701305

18. Unii-908sy76s4g

19. Laquinimod [mi]

20. Laquinimod [who-dd]

21. Laquinimod,abr-215062

22. Schembl39440

23. Schembl39441

24. Mls006010210

25. Mls006010286

26. Chembl66092

27. Gtpl7639

28. Abr-215062 (laquinimod)

29. Amy6804

30. Dtxsid30179536

31. Ex-a079

32. Laquinimod Pound Notabr215062

33. Chebi:134738

34. Hms3656n08

35. Bcp04521

36. Zinc5573462

37. S2787

38. Akos005146322

39. Zinc100004621

40. Bcp9000840

41. Ccg-268120

42. Cs-0839

43. Db06685

44. Pb32648

45. 5-chloro-n-et-4-hydroxy-1-methyl-2-oxo-n-ph-1,2-dihydroquinoline-3-carboxamide

46. N-ethyl-n-phenyl-5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide

47. Ncgc00346701-01

48. Ncgc00346701-07

49. Bs-16743

50. Hy-13010

51. Laquinimod,5-chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic Acid Ethyl-phenyl-amide

52. Bcp0726000056

53. Ft-0698088

54. Sw220142-1

55. J-521632

56. Q3487584

57. 5-chloro-4-hydroxy-1-methyl-2-oxo-n-ethyl-n-phenyl-1,2-dihydroquinoline-3-carboxamide

58. N-ethyl-n-phenyl-5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide

2.4 Create Date

2011-12-26

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₇ClN₂O₃
Molecular Weight	356.8 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	356.0927701 g/mol
Monoisotopic Mass	356.0927701 g/mol
Topological Polar Surface Area	60.8 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	571
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

Investigated for use/treatment in multiple sclerosis.

Treatment of multiple sclerosis

5 Pharmacology and Biochemistry

5.1 ATC Code

N07

N - Nervous system

N07 - Other nervous system drugs

N07X - Other nervous system drugs

N07XX - Other nervous system drugs

N07XX10 - Laquinimod

5.2 Metabolism/Metabolites

Hepatic. Cytochrome P450 3A4 is the major enzyme responsible for the metabolism of laquinimod.

Laquinimod has known human metabolites that include 5-chloro-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide, 5-chloro-N-ethyl-4,6-dihydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide, 5-chloro-N-ethyl-4,7-dihydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide, 5-chloro-N-ethyl-4,8-dihydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide, 5-chloro-N-ethyl-4-hydroxy-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide, and 5-chloro-N-ethyl-4-hydroxy-N-(4-hydroxyphenyl)-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560