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    Adagrasib

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: Mrtx849, 2326521-71-3, Mrtx-849, Adagrasib [usan], Kras g12c inhibitor mrtx849, 8eoo6hqf8y
    Molecular Formula
    C32H35ClFN7O2
    Molecular Weight
    604.1  g/mol
    InChI Key
    PEMUGDMSUDYLHU-ZEQRLZLVSA-N
    FDA UNII
    8EOO6HQF8Y
    Adagrasib is an orally available, small molecule inhibitor that targets the oncogenic KRAS substitution mutation, G12C, with potential antineoplastic activity. Upon oral administration adagrasib covalently binds to cytosine 12 within the switch II pocket of GDP-bound KRAS G12C, thereby inhibiting mutant KRAS-dependent signaling. KRAS, a member of the RAS family of oncogenes, serves an important role in cell signaling, division and differentiation. Mutations of KRAS may induce constitutive signal transduction leading to tumor cell growth, proliferation, invasion, and metastasis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[(2S)-4-[7-(8-chloronaphthalen-1-yl)-2-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]-6,8-dihydro-5H-pyrido[3,4-d]pyrimidin-4-yl]-1-(2-fluoroprop-2-enoyl)piperazin-2-yl]acetonitrile
    2.1.2 InChI
    InChI=1S/C32H35ClFN7O2/c1-21(34)31(42)41-17-16-40(18-23(41)11-13-35)30-25-12-15-39(28-10-4-7-22-6-3-9-26(33)29(22)28)19-27(25)36-32(37-30)43-20-24-8-5-14-38(24)2/h3-4,6-7,9-10,23-24H,1,5,8,11-12,14-20H2,2H3/t23-,24-/m0/s1
    2.1.3 InChI Key
    PEMUGDMSUDYLHU-ZEQRLZLVSA-N
    2.1.4 Canonical SMILES
    CN1CCCC1COC2=NC3=C(CCN(C3)C4=CC=CC5=C4C(=CC=C5)Cl)C(=N2)N6CCN(C(C6)CC#N)C(=O)C(=C)F
    2.1.5 Isomeric SMILES
    CN1CCC[C@H]1COC2=NC3=C(CCN(C3)C4=CC=CC5=C4C(=CC=C5)Cl)C(=N2)N6CCN([C@H](C6)CC#N)C(=O)C(=C)F
    2.2 Other Identifiers
    2.2.1 UNII
    8EOO6HQF8Y
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-((s)-4-(7-(8-chloronaphthalen-1-yl)-2-(((s)-1-methylpyrrolidin-2-yl)methoxy)-5,6,7,8-tetrahydropyrido(3,4-d)pyrimidin-4-yl)-1-(2-fluoroacryloyl)piperazin-2-yl)acetonitrile

    2. 2-piperazineacetonitrile, 4-(7-(8-chloro-1-naphthalenyl)-5,6,7,8-tetrahydro-2-(((2s)-1-methyl-2-pyrrolidinyl)methoxy)pyrido(3,4-d)pyrimidin-4-yl)-1-(2-fluoro-1-oxo-2-propen-1-yl)-, (2s)-

    3. Mrtx-849

    4. Mrtx849

    2.3.2 Depositor-Supplied Synonyms

    1. Mrtx849

    2. 2326521-71-3

    3. Mrtx-849

    4. Adagrasib [usan]

    5. Kras G12c Inhibitor Mrtx849

    6. 8eoo6hqf8y

    7. 2-((s)-4-(7-(8-chloronaphthalen-1-yl)-2-(((s)-1-methylpyrrolidin-2-yl)methoxy)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-1-(2-fluoroacryloyl)piperazin-2-yl)acetonitrile

    8. 2-[(2s)-4-[7-(8-chloronaphthalen-1-yl)-2-[[(2s)-1-methylpyrrolidin-2-yl]methoxy]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-4-yl]-1-(2-fluoroprop-2-enoyl)piperazin-2-yl]acetonitrile

    9. 2-piperazineacetonitrile, 4-[7-(8-chloro-1-naphthalenyl)-5,6,7,8-tetrahydro-2-[[(2s)-1-methyl-2-pyrrolidinyl]methoxy]pyrido[3,4-d]pyrimidin-4-yl]-1-(2-fluoro-1-oxo-2-propen-1-yl)-, (2s)-

    10. 2-piperazineacetonitrile, 4-(7-(8-chloro-1-naphthalenyl)-5,6,7,8-tetrahydro-2-(((2s)-1-methyl-2-pyrrolidinyl)methoxy)pyrido(3,4-d)pyrimidin-4-yl)-1-(2-fluoro-1-oxo-2-propen-1-yl)-, (2s)-

    11. Adagrasib [inn]

    12. Unii-8eoo6hqf8y

    13. Adagrasib [who-dd]

    14. Chembl4594350

    15. Schembl20974691

    16. Gtpl10888

    17. Dtxsid801336759

    18. Bcp31538

    19. Ex-a3258

    20. Mrtx-849; Mrtx 849

    21. Bdbm50539763

    22. Mfcd32263433

    23. Nsc831453

    24. S8884

    25. Who 11519

    26. Akos037648997

    27. At23561

    28. Nsc-831453

    29. Compound 20 [pmid: 32250617]

    30. Ac-35659

    31. Bm177692

    32. Bs-16211

    33. Hy-130149

    34. Cs-0105265

    35. A936721

    36. ((2s)-4-(7-(8-chloronaphthalen-1-yl)-2-(((2s)-1- Methylpyrrolidin-2-yl)methoxy)-5,6,7,8- Tetrahydropyrido(3,4-d)pyrimidin-4-yl)-1-(2-fluoroprop2-enoyl)piperazin-2-yl)acetonitrile

    37. [(2s)-4-[7-(8-chloro-1-naphthyl)-2-{[(2s)-1-methyl-2-pyrrolidinyl]methoxy}-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl]-1-(2-fluoroacryloyl)-2-piperazinyl]acetonitrile

    2.4 Create Date
    2019-07-20
    3 Chemical and Physical Properties
    Molecular Weight 604.1 g/mol
    Molecular Formula C32H35ClFN7O2
    XLogP35
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count7
    Exact Mass603.2524792 g/mol
    Monoisotopic Mass603.2524792 g/mol
    Topological Polar Surface Area88.8 Ų
    Heavy Atom Count43
    Formal Charge0
    Complexity1060
    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

    MRTX849 is an experimental KRAS inhibitor being investigated for the treatment of KRAS G12C mutant lung and colon adenocarcinomas.

    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.)

    5.2 Mechanism of Action

    Normally GTP binds to KRAS, activating the protein and promoting effectors to the MAP kinase pathway. GTP is hydrolyzed to GDP, and KRAS is inactivated. KRAS G12C mutations impair hydrolysis of GTP, leaving it in the active form. MRTX849 inhibits KRAS in these types of cancers. This mutation is present in 13% of non small cell lung cancer, 3% of colorectal and appendix cancer, and 1-3% of solid tumors.