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Sotorasib

Sotorasib

Synopsis, Chemistry

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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

Sotorasib

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 Formula	C₃₀H₃₀F₂N₆O₃
Molecular Weight	560.6 g/mol
XLogP3	4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	5
Exact Mass	560.23474516 g/mol
Monoisotopic Mass	560.23474516 g/mol
Topological Polar Surface Area	102 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	1030
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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 C_max of 7.50 g/mL, with a median T_max of 2.0 hours, and an AUC_0-24h 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.