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Also known as: 1510829-06-7, Biib-062, Bsk-4841, Fp0182, Vecabrutinib [inn], Vecabrutinib [usan]

Molecular Formula

C₂₂H₂₄ClF₄N₇O₂

Molecular Weight

529.9 g/mol

InChI Key

QLRRJMOBVVGXEJ-XHSDSOJGSA-N

FDA UNII

PQ7O0OB5GU

Vecabrutinib is an orally available second-generation, reversible inhibitor of Bruton's tyrosine kinase (BTK; Bruton agammaglobulinemia tyrosine kinase), with potential antineoplastic activity. Upon administration, vecabrutinib non-covalently binds to and inhibits the activity of both wild-type and the C481S mutated form of BTK, a resistance mutation in the BTK active site in which cysteine is substituted for serine at residue 481. This prevents the activation of the B-cell antigen receptor (BCR) signaling pathway and BTK-mediated activation of downstream survival pathways. This leads to an inhibition of the growth of malignant B-cells that overexpress BTK. Compared to other BTK inhibitors, SNS-062 does not require interaction with the BTK C481 site and inhibits the proliferation of cells harboring the BTK C481S mutation. Other irreversible BTK inhibitors covalently bind to the C481 site to inhibit BTK's activity; the C481S mutation prevents that binding. 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 the development, activation, signaling, proliferation and survival of B-lymphocytes.

1 2D Structure

Vecabrutinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3R,4S)-1-(6-amino-5-fluoropyrimidin-4-yl)-3-[(3R)-3-[3-chloro-5-(trifluoromethyl)anilino]-2-oxopiperidin-1-yl]piperidine-4-carboxamide

2.1.2 InChI

InChI=1S/C22H24ClF4N7O2/c23-12-6-11(22(25,26)27)7-13(8-12)32-15-2-1-4-34(21(15)36)16-9-33(5-3-14(16)19(29)35)20-17(24)18(28)30-10-31-20/h6-8,10,14-16,32H,1-5,9H2,(H2,29,35)(H2,28,30,31)/t14-,15+,16-/m0/s1

2.1.3 InChI Key

QLRRJMOBVVGXEJ-XHSDSOJGSA-N

2.1.4 Canonical SMILES

C1CC(C(=O)N(C1)C2CN(CCC2C(=O)N)C3=NC=NC(=C3F)N)NC4=CC(=CC(=C4)C(F)(F)F)Cl

2.1.5 Isomeric SMILES

C1C[C@H](C(=O)N(C1)[C@H]2CN(CC[C@@H]2C(=O)N)C3=NC=NC(=C3F)N)NC4=CC(=CC(=C4)C(F)(F)F)Cl

2.2 Other Identifiers

2.2.1 UNII

PQ7O0OB5GU

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 1510829-06-7

2. Biib-062

3. Bsk-4841

4. Fp0182

5. Vecabrutinib [inn]

6. Vecabrutinib [usan]

7. Pq7o0ob5gu

8. Fp-0182

9. Sns062

10. (3r,3'r,4's)-1'-(6-amino-5-fluoropyrimidin-4-yl)-3-[3-chloro-5-(trifluoromethyl)anilino]-2-oxo[1,3'-bipiperidine]-4'-carboxamide

11. (3r,3'r,4's)-1'-(6-amino-5-fluoropyrimidin-4-yl)-3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-2-oxo-(1,3'-bipiperidine)-4'-carboxamide

12. (3r,3'r,4's)-1'-(6-amino-5-fluoropyrimidin-4-yl)-3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-2-oxo-[1,3'-bipiperidine]-4'-carboxamide

13. Unii-pq7o0ob5gu

14. Vecabrutinib (usan/inn)

15. Vecabrutinib [usan:inn]

16. Biib062

17. Vecabrutinib [who-dd]

18. Chembl4297640

19. Schembl16765727

20. Gtpl10231

21. Bcp29646

22. Ex-a3159

23. Bdbm50546200

24. Fp-182

25. Nsc810114

26. Who 10643

27. Zb1596

28. Nsc-810114

29. Ac-36339

30. Hy-109078

31. Cs-0033553

32. D11428

33. (1,3'-bipiperidine)-4'-carboxamide, 1'-(6-amino-5-fluoro-4-pyrimidinyl)-3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-2-oxo-, (3r,3'r,4's)-

34. (3r,4s)-1-(6-amino-5-fluoropyrimidin-4-yl)-3-[(3r)-3-[3-chloro-5-(trifluoromethyl)anilino]-2-oxopiperidin-1-yl]piperidine-4-carboxamide

2.4 Create Date

2014-01-06

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₄ClF₄N₇O₂
Molecular Weight	529.9 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	5
Exact Mass	529.1616134 g/mol
Monoisotopic Mass	529.1616134 g/mol
Topological Polar Surface Area	131 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	809
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