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Chemistry

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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

Lifirafenib

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 Formula	C₂₅H₁₇F₃N₄O₃
Molecular Weight	478.4 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	3
Exact Mass	478.12527490 g/mol
Monoisotopic Mass	478.12527490 g/mol
Topological Polar Surface Area	89.1 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	845
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1