Fenebrutinib

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Also known as: Gdc-0853, 1434048-34-6, Rg7845, Gdc0853, Rg-7845, Fenebrutinib [inn]

Molecular Formula

C₃₇H₄₄N₈O₄

Molecular Weight

664.8 g/mol

InChI Key

WNEODWDFDXWOLU-QHCPKHFHSA-N

FDA UNII

E9L2885WUL

Fenebrutinib is an orally available inhibitor of Bruton's tyrosine kinase (BTK) with potential antineoplastic activity. Upon administration, fenebrutinib inhibits the activity of BTK and prevents the activation of the B-cell antigen receptor (BCR) signaling pathway. This prevents both B-cell activation and BTK-mediated activation of downstream survival pathways, which leads to the inhibition of the growth of malignant B-cells that overexpress BTK. BTK, a member of the Src-related BTK/Tec family of cytoplasmic tyrosine kinases, is overexpressed in B-cell malignancies; it plays an important role in B-lymphocyte development, activation, signaling, proliferation and survival.

1 2D Structure

Fenebrutinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

10-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2S)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-9-one

2.1.2 InChI

InChI=1S/C37H44N8O4/c1-23-18-42(27-21-49-22-27)9-10-43(23)26-5-6-33(39-17-26)40-30-13-25(19-41(4)35(30)47)28-7-8-38-34(29(28)20-46)45-12-11-44-31(36(45)48)14-24-15-37(2,3)16-32(24)44/h5-8,13-14,17,19,23,27,46H,9-12,15-16,18,20-22H2,1-4H3,(H,39,40)/t23-/m0/s1

2.1.3 InChI Key

WNEODWDFDXWOLU-QHCPKHFHSA-N

2.1.4 Canonical SMILES

CC1CN(CCN1C2=CN=C(C=C2)NC3=CC(=CN(C3=O)C)C4=C(C(=NC=C4)N5CCN6C7=C(CC(C7)(C)C)C=C6C5=O)CO)C8COC8

2.1.5 Isomeric SMILES

C[C@H]1CN(CCN1C2=CN=C(C=C2)NC3=CC(=CN(C3=O)C)C4=C(C(=NC=C4)N5CCN6C7=C(CC(C7)(C)C)C=C6C5=O)CO)C8COC8

2.2 Other Identifiers

2.2.1 UNII

E9L2885WUL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(3'-(hydroxymethyl)-1-methyl-5-((5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)amino)-6-oxo-1,6-dihydro-(3,4'-bipyridin)-2'-yl)-7,7-dimethyl-3,4,7,8-tetrahydro-2h-cyclopenta(4,5)pyrrolo(1,2-a)pyrazin-1(6h)-one

2. Gdc-0853

2.3.2 Depositor-Supplied Synonyms

1. Gdc-0853

2. 1434048-34-6

3. Rg7845

4. Gdc0853

5. Rg-7845

6. Fenebrutinib [inn]

7. Fenebrutinib [usan]

8. Ro7010939

9. E9l2885wul

10. (s)-2-(3'-(hydroxymethyl)-1-methyl-5-((5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)amino)-6-oxo-1,6-dihydro-[3,4'-bipyridin]-2'-yl)-7,7-dimethyl-3,4,7,8-tetrahydro-2h-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1(6h)-one

11. Chembl4065122

12. G02599853

13. Ro-7010939

14. G-02599853

15. 10-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-9-one

16. 2-[3'-(hydroxymethyl)-1-methyl-5-({5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl}amino)-6-oxo[1,6-dihydro[3,4'-bipyridine]]-2'-yl]-7,7-dimethyl-3,4,7,8-tetrahydro-2h-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1(6h)-one

17. Fenebrutinib (usan/inn)

18. Fenebrutinib [usan:inn]

19. Unii-e9l2885wul

20. Fenebrutinib (gdc-0853)

21. Fenebrutinib [who-dd]

22. Gtpl9299

23. Schembl14912882

24. Bcp19175

25. Ex-a1308

26. Gdc 0853

27. Gdc-0853gdc-0853

28. Bdbm50244440

29. Nsc798202

30. S8421

31. Zinc220197997

32. Cs-5927

33. Db14785

34. Gdc-0853(rg7845)

35. Nsc-798202

36. Ac-32585

37. Bs-15120

38. Hy-19834

39. Rg-7845 (gdc-0853)

40. Example 130 [us20140194408]

41. J3.615.209e

42. A16339

43. D11457

44. A904370

45. Q23304817

46. (s)-2-(3'-(hydroxymethyl)-1-methyl-5-((5-(2-methyl- 4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)amino)-6-oxo-1,6-dihydro-(3,4'-bipyridin)-2'-yl)-7,7-dimethyl-2,3,4,6,7,8-hexahydro-1h-cyclopenta (4,5)pyrrolo(1,2-a)pyrazin-1-one

47. 2-(3'-(hydroxymethyl)-1-methyl-5-((5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-yl)amino)-6-oxo-1,6-dihydro-(3,4'-bipyridin)-2'-yl)-7,7-dimethyl-3,4,7,8-tetrahydro-2h-cyclopenta(4,5)pyrrolo(1,2-a)pyrazin-1(6h)-one

48. 2h-cyclopenta(4,5)pyrrolo(1,2-a)pyrazin-1(6h)-one, 2-(1,6-dihydro-3'-(hydroxymethyl)-1-methyl-5-((5-((2s)-2-methyl-4-(3-oxetanyl)-1-piperazinyl)-2-pyridinyl)amino)-6-oxo(3,4'-bipyridin)-2'-yl)-3,4,7,8-tetrahydro-7,7-dimethyl-

49. 2h-cyclopenta(4,5)pyrrolo(1,2-a)pyrazin-1(6h)-one, 2-(1,6-dihydro-3'-(hydroxymethyl)-1-methyl-5-((5-((2s)-2-methyl-4-(3-oxetanyl)-1-piperazinyl)-2-pyridinyl)amino)-6-oxo(3,4'-bipyridin)-2'-yl)3,4,7,8-tetrahydro-7,7-dimethyl-

50. 9aj

2.4 Create Date

2015-01-20

3 Chemical and Physical Properties

Molecular Formula	C₃₇H₄₄N₈O₄
Molecular Weight	664.8 g/mol
XLogP3	2.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	7
Exact Mass	664.34855191 g/mol
Monoisotopic Mass	664.34855191 g/mol
Topological Polar Surface Area	119 Å²
Heavy Atom Count	49
Formal Charge	0
Complexity	1340
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