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    Licofelone

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
    $ API Ref.Price (USD/KG) : 58Xls

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    2D Structure
    Also known as: 156897-06-2, Ml-3000, Licofelone [inn], Ml 3000, 2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetic acid, P5t6bys22y
    Molecular Formula
    C23H22ClNO2
    Molecular Weight
    379.9  g/mol
    InChI Key
    UAWXGRJVZSAUSZ-UHFFFAOYSA-N
    FDA UNII
    P5T6BYS22Y
    Developed by the German pharmaceutical company, Merckle GmbH, together with EuroAlliance partners Alfa Wassermann and Lacer, licofelone (ML3000) is a dual COX/LOX inhibitor and the first member of this new class of analgesic and anti-inflammatory drugs. It is currently under evaluation as a treatment for osteoarthritis (OA), the most common form of arthritis. Although phase III trials have been successfully completed in OA patients no dates for regulatory submission have yet been given.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetic acid
    2.1.2 InChI
    InChI=1S/C23H22ClNO2/c1-23(2)13-19-22(15-6-4-3-5-7-15)21(16-8-10-17(24)11-9-16)18(12-20(26)27)25(19)14-23/h3-11H,12-14H2,1-2H3,(H,26,27)
    2.1.3 InChI Key
    UAWXGRJVZSAUSZ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1(CC2=C(C(=C(N2C1)CC(=O)O)C3=CC=C(C=C3)Cl)C4=CC=CC=C4)C
    2.2 Other Identifiers
    2.2.1 UNII
    P5T6BYS22Y
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (2,2-dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1h-pyrrolizine-5-yl)acetic Acid

    2. Ml 3000

    3. Ml-3000

    2.3.2 Depositor-Supplied Synonyms

    1. 156897-06-2

    2. Ml-3000

    3. Licofelone [inn]

    4. Ml 3000

    5. 2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetic Acid

    6. P5t6bys22y

    7. (6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizin-5-yl)acetic Acid

    8. [6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizin-5-yl]acetic Acid

    9. Chembl300982

    10. 2-(6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizin-5-yl)acetic Acid

    11. Lcf

    12. 2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizin-5-yl]acetic Acid

    13. Unii-p5t6bys22y

    14. Brn 6823674

    15. 6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-1h-pyrrolizine-5-acetic Acid

    16. 2,2-dimethyl-6-(4-chlorophenyl-7-phenyl-2,3-dihydro-1h-pyrrolizine-5-yl)acetic Acid

    17. 2,3-dihydro-6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-1h-pyrrolizine-5-acetic Acid

    18. Licofelone [mi]

    19. Licofelone [mart.]

    20. Mls006011224

    21. Schembl237833

    22. Dtxsid40166154

    23. Hms3655d21

    24. Bcp06598

    25. Hy-b1452

    26. Zinc3805769

    27. Bdbm50038649

    28. Ml3000

    29. S2121

    30. Akos027250758

    31. Db04725

    32. Sb19520

    33. (6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizine-5-yl)-acetic Acid

    34. 1h-pyrrolizine-5-acetic Acid, 2,3-dihydro-6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-

    35. Ncgc00250374-01

    36. Ncgc00250374-02

    37. Ac-33111

    38. As-73938

    39. Smr004702985

    40. Cs-0013159

    41. Ft-0670787

    42. Sw219543-1

    43. Ab01566204_02

    44. 897l062

    45. A809783

    46. J-009352

    47. Q3832015

    48. [2-(4-chloro-phenyl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5h-pyrrolizin-3-yl]-acetic Acid

    49. 1h-pyrrolizine-5-acetic Acid, 6-(4-chlorophenyl)-2,3-dihydro-2,2-dimethyl-7-phenyl-

    50. 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizin-5-ylacetic Acid

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 379.9 g/mol
    Molecular Formula C23H22ClNO2
    XLogP35.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count4
    Exact Mass379.1339066 g/mol
    Monoisotopic Mass379.1339066 g/mol
    Topological Polar Surface Area42.2 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity537
    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

    For the management of osteoarthritis.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Licofelone belongs to a novel class of dual-acting anti-inflammatory drugs called COX/LO inhibitors. This group of drugs simultaneously inhibits the enzymes cyclooxygenase (COX) and 5-lipoxygenase (LO).

    5.2 MeSH Pharmacological Classification

    Cyclooxygenase Inhibitors

    Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)

    Analgesics

    Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)

    Anti-Inflammatory Agents

    Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

    Lipoxygenase Inhibitors

    Compounds that bind to and inhibit that enzymatic activity of LIPOXYGENASES. Included under this category are inhibitors that are specific for lipoxygenase subtypes and act to reduce the production of LEUKOTRIENES. (See all compounds classified as Lipoxygenase Inhibitors.)

    5.3 Metabolism/Metabolites

    Licofelone has known human metabolites that include (2S,3S,4S,5R)-6-[2-[2-(4-chlorophenyl)-6,6-dimethyl-1-phenyl-5,7-dihydropyrrolizin-3-yl]acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid, Licofelone M2, and Licofelone M4.

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

    5.4 Mechanism of Action

    Licofelone, through combined 5-LOX/COX-inhibition, reduces levels of inflammatory prostaglandins and leukotrienes.