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Also known as: 1971920-73-6, Prn2246, C]pyridin-2-one, Sar442168, Tolebrutinib [inn], Tolebrutinib [usan]

Molecular Formula

C₂₆H₂₅N₅O₃

Molecular Weight

455.5 g/mol

InChI Key

KOEUOFPEZFUWRF-LJQANCHMSA-N

FDA UNII

8CZ82ZYY9X

Tolebrutinib is an orally bioavailable, brain-penetrant, selective, small molecule inhibitor of Bruton's tyrosine kinase (BTK), with potential immunomodulatory and anti-inflammatory activities. Upon oral administration, tolebrutinib is able to cross the blood-brain barrier and inhibits the activity of BTK both peripherally and in the central nervous system (CNS). This prevents the activation of the B-cell antigen receptor (BCR) signaling pathway, and the resulting immune activation and inflammation. The inhibition of BTK activity also prevents microglial inflammatory signaling in the CNS, and the resulting immune activation, neuroinflammation and neurodegeneration. BTK, a cytoplasmic tyrosine kinase and member of the Tec family of kinases, plays an important role in B lymphocyte development, activation, signaling, proliferation and survival. In addition to B cells, BTK is also expressed in innate immune cells, including macrophages and microglia, and plays an important role in the regulation of microglial inflammatory signaling.

1 2D Structure

Tolebrutinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-amino-3-(4-phenoxyphenyl)-1-[(3R)-1-prop-2-enoylpiperidin-3-yl]imidazo[4,5-c]pyridin-2-one

2.1.2 InChI

InChI=1S/C26H25N5O3/c1-2-23(32)29-16-6-7-19(17-29)30-22-14-15-28-25(27)24(22)31(26(30)33)18-10-12-21(13-11-18)34-20-8-4-3-5-9-20/h2-5,8-15,19H,1,6-7,16-17H2,(H2,27,28)/t19-/m1/s1

2.1.3 InChI Key

KOEUOFPEZFUWRF-LJQANCHMSA-N

2.1.4 Canonical SMILES

C=CC(=O)N1CCCC(C1)N2C3=C(C(=NC=C3)N)N(C2=O)C4=CC=C(C=C4)OC5=CC=CC=C5

2.1.5 Isomeric SMILES

C=CC(=O)N1CCC[C@H](C1)N2C3=C(C(=NC=C3)N)N(C2=O)C4=CC=C(C=C4)OC5=CC=CC=C5

2.2 Other Identifiers

2.2.1 UNII

8CZ82ZYY9X

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 1971920-73-6

2. Prn2246

3. C]pyridin-2-one

4. Sar442168

5. Tolebrutinib [inn]

6. Tolebrutinib [usan]

7. 8cz82zyy9x

8. Prn-2246

9. 4-amino-3-(4-phenoxyphenyl)-1-[(3r)-1-prop-2-enoylpiperidin-3-yl]imidazo[4,5-c]pyridin-2-one

10. (r)-1-(1-acryloylpiperidin-3-yl)-4-amino-3-(4-phenoxyphenyl)-1h-imidazo[4,5-c]pyridin-2(3h)-one

11. 4-amino-3-(4-phenoxyphenyl)-1-[(3r)-1-(prop-2-

12. Enoyl)piperidin-3-yl]-1,3-dihydro-2h-imidazo[4,5-

13. 2h-imidazo(4,5-c)pyridin-2-one, 4-amino-1,3-dihydro-1-((3r)-1-(1-oxo-2-propen-1-yl)-3-piperidinyl)-3-(4-phenoxyphenyl)-

14. 4-amino-1,3-dihydro-1-((3r)-1-(1-oxo-2-propen-1-yl)-3-piperidinyl)-3-(4-phenoxyphenyl)-2h-imidazo(4,5-c)pyridin-2-one

15. Unii-8cz82zyy9x

16. Tolebrutinib [who-dd]

17. Chembl4650323

18. Schembl18285621

19. Gtpl10625

20. Btk'168

21. Ex-a4699

22. Bdbm50557487

23. Who 11268

24. Sar-442168

25. Example 3 [wo2016196840a1]

26. Sar442168; Prn2246

27. Hy-109192

28. Cs-0119132

2.4 Create Date

2017-02-18

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₅N₅O₃
Molecular Weight	455.5 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Exact Mass	455.19573968 g/mol
Monoisotopic Mass	455.19573968 g/mol
Topological Polar Surface Area	92 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	749
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