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Also known as: 1655504-04-3, Icp-022, Orelabrutinib [inn], Orelabrutinib [usan], Wja5uo9e10, Icp022

Molecular Formula

C₂₆H₂₅N₃O₃

Molecular Weight

427.5 g/mol

InChI Key

MZPVEMOYADUARK-UHFFFAOYSA-N

FDA UNII

WJA5UO9E10

Orelabrutinib is a small molecule inhibitor of Bruton's tyrosine kinase (BTK; Bruton agammaglobulinemia tyrosine kinase) with potential antineoplastic activity. Upon administration, orelabrutinib binds to and inhibits the activity of BTK. This prevents both the activation of the B-cell antigen receptor (BCR) signaling pathway and BTK-mediated activation of downstream survival pathways, inhibiting 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 or mutated in B-cell malignancies; it plays an important role in the development, activation, signaling, proliferation and survival of B-lymphocytes.

1 2D Structure

Orelabrutinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(4-phenoxyphenyl)-6-(1-prop-2-enoylpiperidin-4-yl)pyridine-3-carboxamide

2.1.2 InChI

InChI=1S/C26H25N3O3/c1-2-24(30)29-16-14-18(15-17-29)23-13-12-22(26(27)31)25(28-23)19-8-10-21(11-9-19)32-20-6-4-3-5-7-20/h2-13,18H,1,14-17H2,(H2,27,31)

2.1.3 InChI Key

MZPVEMOYADUARK-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C=CC(=O)N1CCC(CC1)C2=NC(=C(C=C2)C(=O)N)C3=CC=C(C=C3)OC4=CC=CC=C4

2.2 Other Identifiers

2.2.1 UNII

WJA5UO9E10

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 1655504-04-3

2. Icp-022

3. Orelabrutinib [inn]

4. Orelabrutinib [usan]

5. Wja5uo9e10

6. Icp022

7. 6-[1-(1-oxo-2-propen-1-yl)-4-piperidinyl]-2-(4-phenoxyphenyl)-3-pyridinecarboxamide

8. 6-(1-acryloylpiperidin-4-yl)-2-(4-phenoxyphenyl)nicotinamide

9. 2-(4-phenoxyphenyl)-6-(1-prop-2-enoylpiperidin-4-yl)pyridine-3-carboxamide

10. 3-pyridinecarboxamide, 6-(1-(1-oxo-2-propen-1-yl)-4-piperidinyl)-2-(4-phenoxyphenyl)-

11. 6-(1-(1-oxo-2-propen-1-yl)-4-piperidinyl)-2-(4-phenoxyphenyl)-3-pyridinecarboxamide

12. Innobruka

13. Unii-wja5uo9e10

14. Orelabrutinib [who-dd]

15. Chembl4650321

16. Schembl16597834

17. Us9951056, Example 3

18. Gtpl10629

19. Icp-022icp-022

20. Bdbm389631

21. Ex-a3442

22. Nsc826039

23. S9600

24. Who 11190

25. Nsc-826039

26. Example 3 [wo2015048662a2]

27. Ac-36680

28. Db-091042

29. Hy-129390

30. Cs-0105163

2.4 Create Date

2015-04-13

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₅N₃O₃
Molecular Weight	427.5 g/mol
XLogP3	3.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Exact Mass	427.18959167 g/mol
Monoisotopic Mass	427.18959167 g/mol
Topological Polar Surface Area	85.5 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	647
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	1