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    CAS 1223405-08-0

    PharmaCompass
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    2D Structure
    Also known as: 1223405-08-0, Loxo-101 sulfate, Arry-470 sulfate, Loxo-101 (sulfate), (s)-n-(5-((r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide sulfate, Rdf76r62id
    Molecular Formula
    C21H24F2N6O6S
    Molecular Weight
    526.5  g/mol
    InChI Key
    PXHANKVTFWSDSG-QLOBERJESA-N
    FDA UNII
    RDF76R62ID
    Larotrectinib Sulfate is the sulfate salt form of larotrectinib, an orally available, tropomyosin receptor kinase (Trk) inhibitor, with potential antineoplastic activity. Upon administration, larotrectinib binds to Trk, thereby preventing neurotrophin-Trk interaction and Trk activation, which results in both the induction of cellular apoptosis and the inhibition of cell growth in tumors that overexpress Trk. Trk, a receptor tyrosine kinase activated by neurotrophins, is mutated in a variety of cancer cell types and plays an important role in tumor cell growth and survival.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxypyrrolidine-1-carboxamide;sulfuric acid
    2.1.2 InChI
    InChI=1S/C21H22F2N6O2.H2O4S/c22-13-3-4-16(23)15(10-13)18-2-1-7-28(18)19-6-9-29-20(26-19)17(11-24-29)25-21(31)27-8-5-14(30)12-27;1-5(2,3)4/h3-4,6,9-11,14,18,30H,1-2,5,7-8,12H2,(H,25,31);(H2,1,2,3,4)/t14-,18+;/m0./s1
    2.1.3 InChI Key
    PXHANKVTFWSDSG-QLOBERJESA-N
    2.1.4 Canonical SMILES
    C1CC(N(C1)C2=NC3=C(C=NN3C=C2)NC(=O)N4CCC(C4)O)C5=C(C=CC(=C5)F)F.OS(=O)(=O)O
    2.1.5 Isomeric SMILES
    C1C[C@@H](N(C1)C2=NC3=C(C=NN3C=C2)NC(=O)N4CC[C@@H](C4)O)C5=C(C=CC(=C5)F)F.OS(=O)(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    RDF76R62ID
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (3s)-n-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo(1,5-a)pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide

    2. Arry-470

    3. Arry470

    4. Bay-2757556

    5. Bay2757556

    6. Larotrectinib

    7. Loxo-101

    8. Loxo101

    9. N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo(1,5-a)pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide

    10. Vitrakvi

    2.3.2 Depositor-Supplied Synonyms

    1. 1223405-08-0

    2. Loxo-101 Sulfate

    3. Arry-470 Sulfate

    4. Loxo-101 (sulfate)

    5. (s)-n-(5-((r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide Sulfate

    6. Rdf76r62id

    7. Larotrectinib Sulfate [usan]

    8. Vitrakvi

    9. (3s)-n-[5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxypyrrolidine-1-carboxamide;sulfuric Acid

    10. 1-pyrrolidinecarboxamide, N-(5-((2r)-2-(2,5-difluorophenyl)-1-pyrrolidinyl)pyrazolo(1,5-a)pyrimidin-3-yl)-3-hydroxy-, (3s)-, Sulfate (1:1)

    11. Vitrakvi (tn)

    12. 1-pyrrolidinecarboxamide, N-[5-[(2r)-2-(2,5-difluorophenyl)-1-pyrrolidinyl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxy-, (3s)-, Sulfate (1:1)

    13. Larotrectinib (loxo-101) Sulfate

    14. Larotrectinib Sulphate

    15. Loxo-101(sulfate)

    16. Arry-470 (sulfate)

    17. Unii-rdf76r62id

    18. Schembl2239598

    19. Chembl3989939

    20. Ex-a1981a

    21. Dtxsid401026485

    22. Hms3886n19

    23. Larotrectinib Sulfate (jan/usan)

    24. Larotrectinib Sulfate [mi]

    25. Larotrectinib Sulfate [jan]

    26. Amy12423

    27. Larotrectinib (loxo-101 Sulfate)

    28. Hy-12866a

    29. Mfcd29472286

    30. S7960

    31. Larotrectinib Sulfate [who-dd]

    32. Ccg-269890

    33. Cs-5314

    34. Ac-30671

    35. Bl161518

    36. Larotrectinib Sulfate [orange Book]

    37. D11138

    38. (3s)-n-(5-((2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo(1,5-a)pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide Sulfate (1:1)

    39. (s)-n-(5-((r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide Hydrogen Sulfate

    2.4 Create Date
    2012-11-30
    3 Chemical and Physical Properties
    Molecular Weight 526.5 g/mol
    Molecular Formula C21H24F2N6O6S
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count3
    Exact Mass526.14461000 g/mol
    Monoisotopic Mass526.14461000 g/mol
    Topological Polar Surface Area169 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity741
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Indication

    Vitrakvi as monotherapy is indicated for the treatment of adult and paediatric patients with solid tumours that display a Neurotrophic Tyrosine Receptor Kinase (NTRK) gene fusion,

    - who have a disease that is locally advanced, metastatic or where surgical resection is likely to result in severe morbidity, and

    - who have no satisfactory treatment options.

    5 Pharmacology and Biochemistry
    5.1 ATC Code

    L01XE53