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    Odanacatib

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 603139-19-1, Mk-0822, Odanacatib (mk-0822), Mk0822, Mk 0822, Odanacatib (mk0822)
    Molecular Formula
    C25H27F4N3O3S
    Molecular Weight
    525.6  g/mol
    InChI Key
    FWIVDMJALNEADT-SFTDATJTSA-N
    FDA UNII
    N673F6W2VH
    Odanacatib is an inhibitor of cathepsin K with potential anti-osteoporotic activity. Odanacatib selectively binds to and inhibits the activity of cathepsin K, which may result in a reduction in bone resorption, improvement of bone mineral density, and a reversal in osteoporotic changes. Cathepsin K, a tissue-specific cysteine protease that catalyzes degradation of bone matrix proteins such as collagen I/II, elastin, and osteonectin plays an important role in osteoclast function and bone resorption.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-N-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-[[(1S)-2,2,2-trifluoro-1-[4-(4-methylsulfonylphenyl)phenyl]ethyl]amino]pentanamide
    2.1.2 InChI
    InChI=1S/C25H27F4N3O3S/c1-23(2,26)14-20(22(33)32-24(15-30)12-13-24)31-21(25(27,28)29)18-6-4-16(5-7-18)17-8-10-19(11-9-17)36(3,34)35/h4-11,20-21,31H,12-14H2,1-3H3,(H,32,33)/t20-,21-/m0/s1
    2.1.3 InChI Key
    FWIVDMJALNEADT-SFTDATJTSA-N
    2.1.4 Canonical SMILES
    CC(C)(CC(C(=O)NC1(CC1)C#N)NC(C2=CC=C(C=C2)C3=CC=C(C=C3)S(=O)(=O)C)C(F)(F)F)F
    2.1.5 Isomeric SMILES
    CC(C)(C[C@@H](C(=O)NC1(CC1)C#N)N[C@@H](C2=CC=C(C=C2)C3=CC=C(C=C3)S(=O)(=O)C)C(F)(F)F)F
    2.2 Other Identifiers
    2.2.1 UNII
    N673F6W2VH
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. L-1037536

    2. Mk-0822

    2.3.2 Depositor-Supplied Synonyms

    1. 603139-19-1

    2. Mk-0822

    3. Odanacatib (mk-0822)

    4. Mk0822

    5. Mk 0822

    6. Odanacatib (mk0822)

    7. Odanacatib (mk 0822)

    8. Chembl481611

    9. N673f6w2vh

    10. (s)-n-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-(((s)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethyl)amino)pentanamide

    11. (2s)-n-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-[[(1s)-2,2,2-trifluoro-1-[4-(4-methylsulfonylphenyl)phenyl]ethyl]amino]pentanamide

    12. (2s)-n-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-[[(1s)-2,2,2-trifluoro-1-[4'-(methylsulfonyl)[1,1'-biphenyl]-4-yl]ethyl]amino]pentanamide

    13. (s)-n-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-((s)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)biphenyl-4-yl)ethylamino)pentanamide

    14. Odanacatib [usan]

    15. Odanacatib [usan:inn]

    16. Unii-n673f6w2vh

    17. (2s)-n-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-(((1s)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)(1,1'-biphenyl)-4-yl)ethyl)amino)pentanamide

    18. Mk-0822a

    19. Odanacatib [mi]

    20. Odanacatib [inn]

    21. Odanacatib [jan]

    22. Odanacatib (jan/usan)

    23. Odanacatib [mart.]

    24. Odanacatib [who-dd]

    25. Mls006010197

    26. Gtpl6478

    27. L-1037536

    28. Schembl1496266

    29. Dtxsid40209075

    30. Ex-a552

    31. Bcpp000141

    32. Cas:603139-19-1;odanacatib

    33. Bdbm50255753

    34. Mfcd11042419

    35. Nsc766811

    36. S1115

    37. Zinc42893657

    38. Akos015900719

    39. Bcp9001020

    40. Ccg-269888

    41. Cs-0277

    42. Db06670

    43. Nsc-766811

    44. Ncgc00346637-01

    45. Ac-27468

    46. As-19562

    47. Hy-10042

    48. Smr004676504

    49. Sw219669-1

    50. D08955

    51. Mk-0822;mk 0822;mk0822

    52. 139m191

    53. J-690332

    54. Q2014070

    55. N-(1-cyanocyclopropyl)-4-fluoro-n2-{(1s)-2,2,2-trifluoro-1-[4'-(methylsulfonyl)biphenyl-4-yl]ethyl}-l-leucinamide

    56. N1-(1-cyanocyclopropyl)-4-fluoro-n2-{(1s)-2,2,2-trifluoro-1-[4'-(methyl Sulfonyl)-1,1'-biphenyl-4-yl]ethyl}-l-leucinamide

    57. N1-(1-cyanocyclopropyl)-4-fluoro-n2-{(1s)-2,2,2-trifluoro-1-[4'-(methylsulfonyl)-1,1'-biphenyl-4-yl]ethyl}-l-leucinamide

    58. Pentanamide, N-(1-cyanocyclopropyl)-4-fluoro-4-methyl-2-(((1s)-2,2,2-trifluoro-1-(4'-(methylsulfonyl)(1,1'-biphenyl)-4-yl)ethyl)amino)-, (2s)-

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 525.6 g/mol
    Molecular Formula C25H27F4N3O3S
    XLogP34.1
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count9
    Exact Mass525.17092555 g/mol
    Monoisotopic Mass525.17092555 g/mol
    Topological Polar Surface Area107 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity934
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    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 osteoporosis.

    Treatment of osteoporosis

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Increases bone mineral density and reduces risk of fractures in osteoporosis.

    5.2 Absorption, Distribution and Excretion

    Absorption

    Tmax of 2-6h. The absolute bioavailabilities observed with 30mg and 50 mg doses are 70% and 30% respectively. When taken with high fat meals the 50mg dose's bioavailability increases to 49% and tmax increases to 10.5h.

    Route of Elimination

    16.9% excreted in urine. 74.5% excreted in feces.

    Volume of Distribution

    100L

    Clearance

    Total clearance of 0.8L/h.

    5.3 Metabolism/Metabolites

    The major metabolite is the product of hydroxylation by CYP3A4 and CYP2C8. This metabolite is active but is 25 times less effective at inhibiting cathepsin K than odanacatib. The other metabolites are produced through glutathione conjugation, hydrolysis, dealkylation, glucuronidation, oxidation, and cyclization.

    5.4 Biological Half-Life

    Apparent half life observed to be 87.3-94.7h.

    5.5 Mechanism of Action

    Odanacatib inhibits cathepsin K, likely by binding to its active site. Cathepsin K is a cysteine protease enzyme which is secreted by osteoclasts. Cathepsin K is responsible for the breakdown of collagen in the bone matrix as part of bone resorption. The inhibition of this enzyme results in decreased bone resorption without affecting bone deposition resulting in increased bone mineral density. This increased bone mineral density strengthens the bone which leads to fewer fractures in osteoporosis.