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    Naquotinib

    DEVELOPMENTS

    PharmaCompass
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    2D Structure
    Also known as: 1448232-80-1, Asp8273, Naquotinib [usan], Asp-8273, 2-pyrazinecarboxamide, 6-ethyl-3-[[4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]amino]-5-[[(3r)-1-(1-oxo-2-propen-1-yl)-3-pyrrolidinyl]oxy]-, 47dd4548pb
    Molecular Formula
    C30H42N8O3
    Molecular Weight
    562.7  g/mol
    InChI Key
    QKDCLUARMDUUKN-XMMPIXPASA-N
    FDA UNII
    47DD4548PB
    Naquotinib is an orally available, irreversible, third-generation, mutant-selective, epidermal growth factor receptor (EGFR) inhibitor, with potential antineoplastic activity. Upon oral administration, ASP8273 covalently binds to and inhibits the activity of mutant forms of EGFR, including the T790M EGFR mutant, 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. ASP8273 preferentially inhibits mutated forms of EGFR including T790M, a secondarily acquired resistance mutation, and may have therapeutic benefits in tumors with T790M-mediated resistance when compared to other EGFR tyrosine kinase inhibitors. As this agent is selective towards mutant forms of EGFR, its toxicity profile may be reduced as 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
    6-ethyl-3-[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino]-5-[(3R)-1-prop-2-enoylpyrrolidin-3-yl]oxypyrazine-2-carboxamide
    2.1.2 InChI
    InChI=1S/C30H42N8O3/c1-4-25-30(41-24-12-15-38(20-24)26(39)5-2)34-29(27(33-25)28(31)40)32-21-6-8-22(9-7-21)36-13-10-23(11-14-36)37-18-16-35(3)17-19-37/h5-9,23-24H,2,4,10-20H2,1,3H3,(H2,31,40)(H,32,34)/t24-/m1/s1
    2.1.3 InChI Key
    QKDCLUARMDUUKN-XMMPIXPASA-N
    2.1.4 Canonical SMILES
    CCC1=C(N=C(C(=N1)C(=O)N)NC2=CC=C(C=C2)N3CCC(CC3)N4CCN(CC4)C)OC5CCN(C5)C(=O)C=C
    2.1.5 Isomeric SMILES
    CCC1=C(N=C(C(=N1)C(=O)N)NC2=CC=C(C=C2)N3CCC(CC3)N4CCN(CC4)C)O[C@@H]5CCN(C5)C(=O)C=C
    2.2 Other Identifiers
    2.2.1 UNII
    47DD4548PB
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Asp-8273

    2. Asp8273

    2.3.2 Depositor-Supplied Synonyms

    1. 1448232-80-1

    2. Asp8273

    3. Naquotinib [usan]

    4. Asp-8273

    5. 2-pyrazinecarboxamide, 6-ethyl-3-[[4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]amino]-5-[[(3r)-1-(1-oxo-2-propen-1-yl)-3-pyrrolidinyl]oxy]-

    6. 47dd4548pb

    7. 6-ethyl-3-[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino]-5-[(3r)-1-prop-2-enoylpyrrolidin-3-yl]oxypyrazine-2-carboxamide

    8. (r)-5-((1-acryloylpyrrolidin-3-yl)oxy)-6-ethyl-3-((4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)amino)pyrazine-2-carboxamide

    9. 2-pyrazinecarboxamide, 6-ethyl-3-((4-(4-(4-methyl-1-piperazinyl)-1-piperidinyl)phenyl)amino)-5-(((3r)-1-(1-oxo-2-propen-1-yl)-3-pyrrolidinyl)oxy)-

    10. E-2-carboxamide

    11. Naquotinib [inn]

    12. Naquotinib (usan/inn)

    13. Asp8273 (naquotinib)

    14. Naquotinib; Asp-8273

    15. Naquotinib [who-dd]

    16. Unii-47dd4548pb

    17. Gtpl9248

    18. Chembl3663929

    19. Schembl16196078

    20. Bdbm170514

    21. Ex-a2669

    22. Yhc23280

    23. Nsc793322

    24. S8412

    25. Zinc205341959

    26. Ccg-270060

    27. Cs-5469

    28. Db12036

    29. Nsc-793322

    30. Ac-35709

    31. As-75247

    32. Hy-19729

    33. J3.496.214f

    34. A14408

    35. C91356

    36. D10958

    37. Us9085540, 54

    38. A857977

    39. Q27074546

    40. 5-[[(3r)-1-acryloylpyrrolidine-3-yl]oxy]-6-ethyl-3-[4-[4-(4-methylpiperazine-1-yl)piperidino]anilino]pyrazine-2-carboxamide

    41. 6-ethyl-3-((4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)amino)-5-(((3r)-1-(1-oxoprop-2-en-1-yl)pyrrolidin-3-yl)oxy)pyrazine-2-carboxamide

    42. 6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)-5-{[(3r)-1-(prop-2-enoyl)pyrrolidin-3-yl]oxy}pyrazine-2-carboxamide

    43. 6-ethyl-3-(4-(4-(4-methylpiperazin-1-yl)piperidin- 1-yl)anilino)-5-(((3r)-1-(prop-2-enoyl)pyrrolidin- 3-yl)oxy)pyrazine-2-carboxamide

    44. 6-ethyl-3-(4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)anilino)-5-(((3r)-1-(prop-2-enoyl)pyrrolidin-3-yl)oxy)pyrazine-2-carboxamide

    45. 6-ethyl-3-[[4-[4-(4-methyl-1-piperazinyl)-1-piperidinyl]phenyl]amino]-5-[[(3r)-1-(1-oxo-2-propen-1-yl)-3-pyrrolidinyl]oxy]-2-pyrazinecarboxamide

    46. 6-ethyl-3-[[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]amino]-5-[(3r)-1-prop-2-enoylpyrrolidin-3-yl]oxy-pyrazin

    2.4 Create Date
    2013-09-02
    3 Chemical and Physical Properties
    Molecular Weight 562.7 g/mol
    Molecular Formula C30H42N8O3
    XLogP33.4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count9
    Exact Mass562.33798723 g/mol
    Monoisotopic Mass562.33798723 g/mol
    Topological Polar Surface Area120 Ų
    Heavy Atom Count41
    Formal Charge0
    Complexity883
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 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.)

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