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    Osimertinib

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 1421373-66-1, Azd-9291 mesylate, Azd9291 mesylate, Azd-9291 (mesylate), Mereletinib mesylate, Tagrisso
    Molecular Formula
    C29H37N7O5S
    Molecular Weight
    595.7  g/mol
    InChI Key
    FUKSNUHSJBTCFJ-UHFFFAOYSA-N
    FDA UNII
    RDL94R2A16
    Osimertinib Mesylate is the mesylate salt form of osimertinib, a third-generation, orally available, irreversible, mutant-selective, epidermal growth factor receptor (EGFR) inhibitor, with potential antineoplastic activity. Upon oral administration, osimertinib covalently binds to and inhibits the activity of numerous mutant forms of EGFR, including the secondarily-acquired resistance mutation T790M, L858R, and exon 19 deletions, thereby preventing EGFR-mediated signaling. This may both induce cell death and inhibit tumor growth in EGFR-overexpressing tumor cells. EGFR, a receptor tyrosine kinase mutated in many tumor cell types, plays a key role in tumor cell proliferation and tumor vascularization. As this agent is selective towards mutant forms of EGFR, its toxicity profile may be reduced when compared to non-selective EGFR inhibitors which also inhibit wild-type EGFR.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[2-[2-(dimethylamino)ethyl-methylamino]-4-methoxy-5-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]phenyl]prop-2-enamide;methanesulfonic acid
    2.1.2 InChI
    InChI=1S/C28H33N7O2.CH4O3S/c1-7-27(36)30-22-16-23(26(37-6)17-25(22)34(4)15-14-33(2)3)32-28-29-13-12-21(31-28)20-18-35(5)24-11-9-8-10-19(20)24;1-5(2,3)4/h7-13,16-18H,1,14-15H2,2-6H3,(H,30,36)(H,29,31,32);1H3,(H,2,3,4)
    2.1.3 InChI Key
    FUKSNUHSJBTCFJ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1C=C(C2=CC=CC=C21)C3=NC(=NC=C3)NC4=C(C=C(C(=C4)NC(=O)C=C)N(C)CCN(C)C)OC.CS(=O)(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    RDL94R2A16
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Azd-9291

    2. Azd-9291 Mesylate

    3. Azd9291

    4. Azd9291 Mesylate

    5. Mereletinib

    6. Mereletinib Mesilate

    7. Mereletinib Mesylate

    8. N-(2-((2-(dimethylamino)ethyl)methylamino)-4-methoxy-5-((4-(1-methyl-1h-indol-3-yl)-2-pyrimidinyl)amino)phenyl)-2-propenamide

    9. N-(2-((2-(dimethylamino)ethyl)methylamino)-4-methoxy-5-((4-(1-methyl-1h-indol-3-yl)-2-pyrimidinyl)amino)phenyl)-2-propenamide Methanesulfonate (1:1)

    10. Osimertinib

    11. Osimertinib Mesilate

    12. Tagrisso

    2.3.2 Depositor-Supplied Synonyms

    1. 1421373-66-1

    2. Azd-9291 Mesylate

    3. Azd9291 Mesylate

    4. Azd-9291 (mesylate)

    5. Mereletinib Mesylate

    6. Tagrisso

    7. Osimertinib Mesilate

    8. Mereletinib Mesilate

    9. Osimertinib Mesylate [usan]

    10. Rdl94r2a16

    11. N-[2-[2-(dimethylamino)ethyl-methylamino]-4-methoxy-5-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]phenyl]prop-2-enamide;methanesulfonic Acid

    12. N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-4-methoxy-5-((4-(1-methyl-1h-indol-3-yl)pyrimidin-2-yl)amino)phenyl)acrylamide Methanesulfonate

    13. Osimertinib Mesilate (jan)

    14. Osimertinib Mesylate (usan)

    15. 2-propenamide, N-(2-((2-(dimethylamino)ethyl)methylamino)-4-methoxy-5-((4-(1-methyl-1h-indol-3-yl)-2-pyrimidinyl)amino)phenyl)-, Methanesulfonate (1:1)

    16. Osimertinib Mesilate [jan]

    17. 2-propenamide, N-[2-[[2-(dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(1-methyl-1h-indol-3-yl)-2-pyrimidinyl]amino]phenyl]-, Compd. With Methanesulfonate (1:2)

    18. Unii-rdl94r2a16

    19. Tagrisso (tn)

    20. Osimertinib Monomesylate

    21. Azd 9291 Mesylate

    22. Osimertinib Methanesulfonate

    23. Amy226

    24. Chembl3545063

    25. Schembl14661152

    26. Chebi:90948

    27. Osimertinib Mesylate [mi]

    28. Dtxsid101027822

    29. Bcp09934

    30. Ex-a1577

    31. Hy-15772a

    32. Mfcd28137994

    33. Osimertinib Mesilate [who-dd]

    34. Akos026673944

    35. Ds-9913

    36. Sb22953

    37. Ac-29022

    38. Da-35303

    39. Osimertinib Mesylate [orange Book]

    40. Azd-9291 Mesylate (osimertinibmereletinib)

    41. Ft-0699962

    42. S5078

    43. D10766

    44. Q27162942

    45. Azd9291 Ms Salt, Osimertinib Ms Salt; Mereletinib Ms Salt

    46. N-(2-{[2-(dimethylamino)ethyl](methyl)amino}-4-methoxy-5-{[4-(1-methyl-1h-indol-3-yl)pyrimidin-2-yl]amino}phenyl)prop-2-enamide Methanesulfonate

    47. N-[2-[[2-(dimethylamino)ethyl]methylamino]-4-methoxy-5-[[4-(1-methyl-1h-indol-3-yl)-2-pyrimidinyl]amino]phenyl]-2-propenamide Methanesulfonate

    2.3.3 Other Synonyms

    1. Osimertinib

    2.4 Create Date
    2014-10-10
    3 Chemical and Physical Properties
    Molecular Weight 595.7 g/mol
    Molecular Formula C29H37N7O5S
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count10
    Exact Mass595.25768848 g/mol
    Monoisotopic Mass595.25768848 g/mol
    Topological Polar Surface Area150 Ų
    Heavy Atom Count42
    Formal Charge0
    Complexity845
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    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

    TAGRISSO as monotherapy is indicated for:

    -the adjuvant treatment after complete tumour resection in adult patients with stage IB-IIIA non-small cell lung cancer (NSCLC) whose tumours have epidermal growth factor receptor (EGFR) exon 19 deletions or exon 21 (L858R) substitution mutations

    - the first-line treatment of adult patients NSCLC with activating EGFR mutations.

    - the treatment of adult patients with locally advanced or metastatic EGFR T790M mutation-positive NSCLC.

    TAGRISSO as monotherapy is indicated for:

    - the adjuvant treatment after complete tumour resection in adult patients with stage IB-IIIA non-small cell lung cancer (NSCLC) whose tumours have epidermal growth factor receptor (EGFR) exon 19 deletions or exon 21 (L858R) substitution mutations.

    - the first-line treatment of adult patients with locally advanced or metastatic NSCLC with activating EGFR mutations.

    - the treatment of adult patients with locally advanced or metastatic EGFR T790M mutation-positive NSCLC.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    Protein Kinase Inhibitors

    Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)

    5.2 ATC Code

    L01XE