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Chemistry

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Also known as: 1800046-95-0, Gs-syk, Lanraplenib [inn], Lanraplenib [usan], Lanraplenib (gs-9876), A6u64ou57e

Molecular Formula

C₂₃H₂₅N₉O

Molecular Weight

443.5 g/mol

InChI Key

XCIGZBVOUQVIPI-UHFFFAOYSA-N

FDA UNII

A6U64OU57E

Lanraplenib is an orally available inhibitor of spleen tyrosine kinase (Syk), with potential immunomodulating and antineoplastic activities. Upon oral administration, lanraplenib binds to and inhibits the activity of Syk. This inhibits B-cell receptor (BCR) signaling, which leads to the inhibition of B-cell activation, and prevents tumor cell activation, migration, adhesion and proliferation. Syk, a non-receptor cytoplasmic, BCR-associated tyrosine kinase, is expressed in hematopoietic tissues and is often overexpressed in hematopoietic malignancies; it plays a key role in B-cell receptor signaling.

1 2D Structure

Lanraplenib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

6-(6-aminopyrazin-2-yl)-N-[4-[4-(oxetan-3-yl)piperazin-1-yl]phenyl]imidazo[1,2-a]pyrazin-8-amine

2.1.2 InChI

InChI=1S/C23H25N9O/c24-21-12-25-11-19(28-21)20-13-32-6-5-26-23(32)22(29-20)27-16-1-3-17(4-2-16)30-7-9-31(10-8-30)18-14-33-15-18/h1-6,11-13,18H,7-10,14-15H2,(H2,24,28)(H,27,29)

2.1.3 InChI Key

XCIGZBVOUQVIPI-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CN(CCN1C2COC2)C3=CC=C(C=C3)NC4=NC(=CN5C4=NC=C5)C6=CN=CC(=N6)N

2.2 Other Identifiers

2.2.1 UNII

A6U64OU57E

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 1800046-95-0

2. Gs-syk

3. Lanraplenib [inn]

4. Lanraplenib [usan]

5. Lanraplenib (gs-9876)

6. A6u64ou57e

7. 6-(6-aminopyrazin-2-yl)-n-[4-[4-(oxetan-3-yl)piperazin-1-yl]phenyl]imidazo[1,2-a]pyrazin-8-amine

8. Gs-9876

9. 6-(6-amino-2-pyrazinyl)-n-[4-[4-(3-oxetanyl)-1-piperazinyl]phenyl]-imidazo[1,2-a]

10. 6-(6-aminopyrazin-2-yl)-n-(4-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)imidazo[1,2-a]pyrazin-8-amine

11. 6-(6-amino-2-pyrazinyl)-n-(4-(4-(3-oxetanyl)-1-piperazinyl)phenyl)imidazo(1,2-a)pyrazin-8-amine

12. Imidazo(1,2-a)pyrazin-8-amine, 6-(6-amino-2-pyrazinyl)-n-(4-(4-(3-oxetanyl)-1-piperazinyl)phenyl)-

13. 6-(6-aminopyrazin-2-yl)-n-{4-[4-(oxetan-3-yl)piperazin-1-yl]phenyl}imidazo[1,2-a]pyrazin-8-amine

14. Gs-syk?

15. Lanraplenib (usan/inn)

16. Lanraplenib [usan:inn]

17. Unii-a6u64ou57e

18. Lanraplenib [who-dd]

19. Gtpl9764

20. Chembl3986824

21. Schembl16820581

22. Example 2 [us9290505]

23. Bdbm212271

24. Bcp30292

25. Ex-a3747

26. Gs9876

27. S9715

28. Who 10601

29. Db14770

30. Gs-9876gs-9876

31. Ex.-2, Us9290505

32. Us9290505, Ex.-2

33. Compound 39 [pmid: 32292557]

34. Ac-36571

35. Hy-109091

36. Cs-0039383

37. C92666

38. D11596

39. Gs-9876; Gs9876; Gs 9876

40. 6-(6-aminopyrazin-2-yl)-n-(4-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)imidazol[1,2-a]pyrazin-8-amine

2.4 Create Date

2016-02-23

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₅N₉O
Molecular Weight	443.5 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	5
Exact Mass	443.21820645 g/mol
Monoisotopic Mass	443.21820645 g/mol
Topological Polar Surface Area	110 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	635
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