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26 US Patents
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2 Health Canada Patents

Egis Osimertinib Mesylate

Synopsis

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Chemistry

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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

Osimertinib Mesylate

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 Formula	C₂₉H₃₇N₇O₅S
Molecular Weight	595.7 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	10
Exact Mass	595.25768848 g/mol
Monoisotopic Mass	595.25768848 g/mol
Topological Polar Surface Area	150 Å²
Heavy Atom Count	42
Formal Charge	0
Complexity	845
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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

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