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    Laquinimod

    DEVELOPMENTS

    DIGITAL CONTENT

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    2D Structure
    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

    2D Structure

    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 Weight 356.8 g/mol
    Molecular Formula C19H17ClN2O3
    XLogP33.7
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count3
    Exact Mass356.0927701 g/mol
    Monoisotopic Mass356.0927701 g/mol
    Topological Polar Surface Area60.8 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity571
    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 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