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    Sotorasib

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: Amg-510, Amg510, 2296729-00-3, Lumakras, Amg-510 racemate, Amg 510
    Molecular Formula
    C30H30F2N6O3
    Molecular Weight
    560.6  g/mol
    InChI Key
    NXQKSXLFSAEQCZ-SFHVURJKSA-N
    FDA UNII
    2B2VM6UC8G
    Sotorasib is an orally available inhibitor of the specific KRAS mutation, p.G12C, with potential antineoplastic activity. Upon oral administration, sotorasib selectively targets, binds to and inhibits the activity of the KRAS p.G12C mutant. This may inhibit growth in KRAS p.G12C-expressing tumor cells. The KRAS p.G12C mutation is seen in some tumor cell types and plays a key role in tumor cell proliferation.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(4-methyl-2-propan-2-ylpyridin-3-yl)-4-[(2S)-2-methyl-4-prop-2-enoylpiperazin-1-yl]pyrido[2,3-d]pyrimidin-2-one
    2.1.2 InChI
    InChI=1S/C30H30F2N6O3/c1-6-23(40)36-12-13-37(18(5)15-36)28-19-14-21(32)26(24-20(31)8-7-9-22(24)39)34-29(19)38(30(41)35-28)27-17(4)10-11-33-25(27)16(2)3/h6-11,14,16,18,39H,1,12-13,15H2,2-5H3/t18-/m0/s1
    2.1.3 InChI Key
    NXQKSXLFSAEQCZ-SFHVURJKSA-N
    2.1.4 Canonical SMILES
    CC1CN(CCN1C2=NC(=O)N(C3=NC(=C(C=C32)F)C4=C(C=CC=C4F)O)C5=C(C=CN=C5C(C)C)C)C(=O)C=C
    2.1.5 Isomeric SMILES
    C[C@H]1CN(CCN1C2=NC(=O)N(C3=NC(=C(C=C32)F)C4=C(C=CC=C4F)O)C5=C(C=CN=C5C(C)C)C)C(=O)C=C
    2.2 Other Identifiers
    2.2.1 UNII
    2B2VM6UC8G
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(4-methyl-2-propan-2-ylpyridin-3-yl)-4-((2s)-2-methyl-4-prop-2-enoylpiperazin-1-yl)pyrido(2,3-d)pyrimidin-2-one

    2. Amg 510

    3. Amg-510

    4. Amg510

    5. Lumakras

    2.3.2 Depositor-Supplied Synonyms

    1. Amg-510

    2. Amg510

    3. 2296729-00-3

    4. Lumakras

    5. Amg-510 Racemate

    6. Amg 510

    7. 2252403-56-6

    8. Kras G12c Inhibitor 9

    9. Sotorasib [inn]

    10. Sotorasib [usan]

    11. Kras Mutant-targeting Amg 510

    12. 4-((s)-4-acryloyl-2-methylpiperazin-1-yl)-6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(2-isopropyl-4-methylpyridin-3-yl)pyrido[2,3-d]pyrimidin-2(1h)-one

    13. 2b2vm6uc8g

    14. Chembl4535757

    15. 2296729-00-3 (racemate)

    16. 6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(4-methyl-2-propan-2-ylpyridin-3-yl)-4-[(2s)-2-methyl-4-prop-2-enoylpiperazin-1-yl]pyrido[2,3-d]pyrimidin-2-one

    17. (1m)-6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(4-methyl-2-(propan-2-yl)pyridin-3-yl)-4-((2s)-2-methyl-4-(prop-2-enoyl)piperazin-1-yl)pyrido(2,3-d)pyrimidin-2(1h)-one

    18. (1s)-4-((s)-4-acryloyl-2-methylpiperazin-1-yl)-6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(2-isopropyl-4-methylpyridin-3-yl)pyrido[2,3-d]pyrimidin-2(1h)-one

    19. 2296729-66-1

    20. 6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(4-methyl-2-propan-2-ylpyridin-3-yl)-4-((2s)-2-methyl-4-prop-2-enoylpiperazin-1-yl)pyrido(2,3-d)pyrimidin-2-one

    21. Pyrido(2,3-d)pyrimidin-2(1h)-one, 6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(4-methyl-2-(1-methylethyl)-3-pyridinyl)-4-((2s)-2-methyl-4-(1-oxo-2-propen-1-yl)-1-piperazinyl)-

    22. Sotorasibum

    23. Lumykras

    24. Pyrido(2,3-d)pyrimidin-2(1h)-one, 6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(4-methyl-2-(1-methylethyl)-3-pyridinyl)-4-((2s)-2-methyl-4-(1-oxo-2-propen-1-yl)-1-piperazinyl)-, (1r)-

    25. Pyrido[2,3-d]pyrimidin-2(1h)-one, 6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-[4-methyl-2-(1-methylethyl)-3-pyridinyl]-4-[(2s)-2-methyl-4-(1-oxo-2-propen-1-yl)-1-piperazinyl]-, (1r)-

    26. Amg510 Racemate

    27. Amg 510 Racemate

    28. Amg-510(racemate)

    29. Sotorasib [jan]

    30. Sotorasib Racemate

    31. Unii-2b2vm6uc8g

    32. Sotorasib [who-dd]

    33. Sotorasib [orange Book]

    34. Schembl20560375

    35. Gtpl10678

    36. Chebi:178199

    37. Amg 510 Pound>>amg-510

    38. Dtxsid001099260

    39. Glxc-25372

    40. Amy16918

    41. Bcp30452

    42. Bcp33368

    43. Ex-a3538

    44. Bdbm50514402

    45. Nsc818433

    46. S8830

    47. Who 11370

    48. Akos037649138

    49. Db15569

    50. Nsc-818433

    51. Ac-35168

    52. Ba172505

    53. Ba172506

    54. Bs-16684

    55. Hy-114277

    56. Cs-0081316

    57. Compound (r)-38 [pmid: 31820981]

    58. D70074

    59. D77975

    60. A930071

    61. A934531

    62. Amg510 ; Amg 510; Amg-510; Amg510

    63. (1r)-4-((s)-4-acryloyl-2-methylpiperazin-1-yl)-6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-(2-isopropyl-4-methylpyridin-3-yl)pyrido[2,3-d]pyrimidin-2(1h)-one

    64. (1ra)-6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-4-((2s)-2-methyl-4-(1-oxoprop-2-en-1-yl)piperazin-1-yl)-1-(4-methyl-2-(propan-2-yl)pyridin-3-yl)pyrido(2,3-d)pyrimidin-2(1h)-one

    65. 6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-(1m)-1-(4-methyl-2-(propan-2-yl)pyridin-3-yl)-4-((2s)-2-methyl-4-(prop-2-enoyl)piperazin-1-yl)pyrido(2,3-d)pyrimidin-2(1h)-one

    66. 6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-[4-methyl-2-(2-propanyl)-3-pyridinyl]-4-[(2s)-2-methyl-4-(2-propenoyl)-1-piperazinyl]pyrido[2,3-d]pyrimidin-2(1h)-one

    67. 6-fluoro-7-(2-fluoro-6-hydroxyphenyl)-1-[4-methyl-2-(propan-2-yl)pyridin-3-yl]-4-[(2s)-2-methyl-4-(prop-2-enoyl)piperazin-1-yl]pyrido[2,3-d]pyrimidin-2(1h)-one

    2.4 Create Date
    2019-01-26
    3 Chemical and Physical Properties
    Molecular Weight 560.6 g/mol
    Molecular Formula C30H30F2N6O3
    XLogP34
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count5
    Exact Mass560.23474516 g/mol
    Monoisotopic Mass560.23474516 g/mol
    Topological Polar Surface Area102 Ų
    Heavy Atom Count41
    Formal Charge0
    Complexity1030
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    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

    Sotorasib is indicated in the treatment of adults with KRAS G12C mutant non small cell lung cancer.

    Lumykras as monotherapy is indicated for the treatment of adults with advanced non-small cell lung cancer (NSCLC) with KRAS G12C mutation and who have progressed after at least one prior line of systemic therapy.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Sotorasib is indicated in the treatment of adults with KRAS G12C mutant non small cell lung cancer. It has a moderate duration of action as it is given daily. Patients should be counselled regarding the risks of hepatotoxicity, interstitial lung disease and pneumonitis; and to avoid breastfeeding during treatment and up to 1 week after the last dose.

    5.2 MeSH Pharmacological Classification

    Immune Checkpoint Inhibitors

    Drugs that block negative regulator IMMUNE CHECKPOINT proteins (e.g., PD-1 RECEPTOR and CTLA-4 ANTIGEN) thereby increasing suppressed immune activation in immunotherapies. (See all compounds classified as Immune Checkpoint Inhibitors.)

    5.3 ATC Code

    L01XX73

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01X - Other antineoplastic agents

    L01XX - Other antineoplastic agents

    L01XX73 - Sotorasib

    5.4 Absorption, Distribution and Excretion

    Absorption

    A 960 mg once daily dose of sotorasib reaches a Cmax of 7.50 g/mL, with a median Tmax of 2.0 hours, and an AUC0-24h of 65.3 h\*g/mL.

    Route of Elimination

    Sotorasib is 74% eliminated in the feces and 6% eliminated in the urine. 53% of the dose recovered in the feces and 1% of the dose recovered in the urine is in the form of the unchanged parent compound.

    Volume of Distribution

    The volume of distribution of sotorasib is 211 L.

    Clearance

    Sotorasib has an apparent clearance at steady state of 26.2 L/h.

    5.5 Metabolism/Metabolites

    Sotorasib is predominantly metabolized through conjugation or by CYP3As.

    5.6 Biological Half-Life

    Sotorasib has a terminal elimination half life of 5.5 1.8 hours.

    5.7 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. Sotorasib binds to the cysteine residue in KRAS G12C mutations, holding the protein in its inactive form. The cysteine residue that sotorasib targets is not present in the wild type KRAS, which prevents off-target effects. This mutation is present in 13% of non small cell lung cancer, 3% of colorectal and appendix cancer, and 1-3% of solid tumors.