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2D Structure
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

2D Structure

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 Weight 443.5 g/mol
Molecular Formula C23H25N9O
XLogP31.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count5
Exact Mass443.21820645 g/mol
Monoisotopic Mass443.21820645 g/mol
Topological Polar Surface Area110 Ų
Heavy Atom Count33
Formal Charge0
Complexity635
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1