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Technical details about Lifirafenib, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
1. Also known as: Lifirafenib, Bgb-283, 1446090-77-2, 1446090-79-4, Bgb283, Lifirafenib [usan]
Molecular Formula
C25H17F3N4O3
Molecular Weight
478.4  g/mol
InChI Key
NGFFVZQXSRKHBM-FKBYEOEOSA-N
FDA UNII
8762XZS5ZF

Lifirafenib is an inhibitor of the serine/threonine protein kinase B-raf (BRAF) and epidermal growth factor receptor (EGFR), with potential antineoplastic activity. Lifirafenib selectively binds to and inhibits the activity of BRAF and certain BRAF mutant forms, and EGFR. This prevents BRAF- and EGFR-mediated signaling and inhibits the proliferation of tumor cells that either contain a mutated BRAF gene or express over-activated EGFR. In addition, BGB-283 inhibits mutant forms of the Ras proteins K-RAS and N-RAS. BRAF and EGFR are mutated or upregulated in many tumor cell types.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-[[(1R,1aS,6bR)-1-[6-(trifluoromethyl)-1H-benzimidazol-2-yl]-1a,6b-dihydro-1H-cyclopropa[b][1]benzofuran-5-yl]oxy]-3,4-dihydro-1H-1,8-naphthyridin-2-one
2.1.2 InChI
InChI=1S/C25H17F3N4O3/c26-25(27,28)11-1-4-15-16(9-11)31-24(30-15)21-20-14-10-12(2-5-17(14)35-22(20)21)34-18-7-8-29-23-13(18)3-6-19(33)32-23/h1-2,4-5,7-10,20-22H,3,6H2,(H,30,31)(H,29,32,33)/t20-,21-,22-/m0/s1
2.1.3 InChI Key
NGFFVZQXSRKHBM-FKBYEOEOSA-N
2.1.4 Canonical SMILES
C1CC(=O)NC2=NC=CC(=C21)OC3=CC4=C(C=C3)OC5C4C5C6=NC7=C(N6)C=C(C=C7)C(F)(F)F
2.1.5 Isomeric SMILES
C1CC(=O)NC2=NC=CC(=C21)OC3=CC4=C(C=C3)O[C@H]5[C@@H]4[C@@H]5C6=NC7=C(N6)C=C(C=C7)C(F)(F)F
2.2 Other Identifiers
2.2.1 UNII
8762XZS5ZF
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 5-((1-(6-(trifluoromethyl)-1h-benzo(d)imidazol-2-yl)-1a,6b-dihydro-1h-cyclopropa(b)benzofuran-5-yl)oxy)-3,4-dihydro-1,8-naphthyrdin-2(1h)-one

2. Bgb-283

3. Lifrafenib

2.3.2 Depositor-Supplied Synonyms

1. Lifirafenib

2. Bgb-283

3. 1446090-77-2

4. 1446090-79-4

5. Bgb283

6. Lifirafenib [usan]

7. 5-(((1r,1as,6br)-1-(6-(trifluoromethyl)-1h-benzo[d]imidazol-2-yl)-1a,6b-dihydro-1h-cyclopropa[b]benzofuran-5-yl)oxy)-3,4-dihydro-1,8-naphthyridin-2(1h)-one

8. Bgb 283

9. 8762xzs5zf

10. 5-(((1r,1as,6br)-1-(6-(trifluoromethyl)-1h-benzimidazol-2-yl)-1a,6b-dihydro-1h-cyclopropa(b)benzofuran-5-yl)oxy)-3,4-dihydro-1h-1,8-naphthyridin-2-one

11. 5-[[(1r,1as,6br)-1-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]-1a,6b-dihydro-1h-cyclopropa[b][1]benzofuran-5-yl]oxy]-3,4-dihydro-1h-1,8-naphthyridin-2-one

12. 1,8-naphthyridin-2(1h)-one, 5-(((1r,1as,6br)-1a,6b-dihydro-1-(6-(trifluoromethyl)-1h-benzimidazol-2-yl)-1h-cyclopropa(b)benzofuran-5-yl)oxy)-3,4-dihydro-

13. 5-({(1r,1as,6br)-1-[5-(trifluoromethyl)-1h-benzimidazol-2-yl]-1a,6b-dihydro-1h-cyclopropa[b][1]benzofuran-5-yl}oxy)-3,4-dihydro-1,8-naphthyridin-2(1h)-one

14. Compound 2.2b

15. 5-{{(1r,1as,6br)-1-[5-(trifluoromethyl)-1h-benzimidazol-2-yl]-1a,6b-dihydro-1h-cyclopropa[b][1]benzofuran-5-yl}oxy}-3,4-dihydro-1,8-naphthyridin-2(1h)-one

16. Lifirafenib [inn]

17. Lifirafenib (usan/inn)

18. Unii-8762xzs5zf

19. Bgb-283;beigene-283

20. Lifirafenib [who-dd]

21. Gtpl8958

22. Chembl4209157

23. Schembl15085288

24. Bdbm372968

25. Ex-a1473

26. Us9895376, Compound 2.2b

27. Whc09077

28. Whc09079

29. Lifirafenib;bgb-283;beigene-283

30. Bdbm50453816

31. Who 10554

32. Zinc68764621

33. Cs-6308

34. Db14773

35. Ac-35880

36. Ac-36373

37. Hy-18957

38. D11410

39. A900647

40. Q27075193

41. 3k3

2.4 Create Date
2015-02-13
3 Chemical and Physical Properties
Molecular Weight 478.4 g/mol
Molecular Formula C25H17F3N4O3
XLogP33.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count3
Exact Mass478.12527490 g/mol
Monoisotopic Mass478.12527490 g/mol
Topological Polar Surface Area89.1 Ų
Heavy Atom Count35
Formal Charge0
Complexity845
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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