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Also known as: Ipi-549, 1693758-51-8, Eganelisib [usan], Pi3k-gamma inhibitor ipi-549, Fof5155fmz, Ipi549

Molecular Formula

C₃₀H₂₄N₈O₂

Molecular Weight

528.6 g/mol

InChI Key

XUMALORDVCFWKV-IBGZPJMESA-N

FDA UNII

FOF5155FMZ

Eganelisib is an orally bioavailable, highly selective small molecule inhibitor of the gamma isoform of phosphoinositide-3 kinase (PI3K-gamma) with potential immunomodulating and antineoplastic activities. Upon administration, eganelisib prevents the activation of the PI3K-gamma-mediated signaling pathways, which may lead to a reduction in cellular proliferation in PI3K-gamma-expressing tumor cells. In addition, this agent is able to modulate anti-tumor immune responses and inhibit tumor-mediated immunosuppression. Unlike other isoforms of PI3K, the gamma isoform is overexpressed in certain tumor cell types and immune cells; its expression increases tumor cell proliferation and survival. By selectively targeting the gamma isoform, PI3K signaling in normal, non-neoplastic cells is minimally or not affected, which results in a reduced side effect profile.

1 2D Structure

Eganelisib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-amino-N-[(1S)-1-[8-[2-(1-methylpyrazol-4-yl)ethynyl]-1-oxo-2-phenylisoquinolin-3-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

2.1.2 InChI

InChI=1S/C30H24N8O2/c1-19(34-29(39)26-27(31)35-37-15-7-14-32-28(26)37)24-16-22-9-6-8-21(13-12-20-17-33-36(2)18-20)25(22)30(40)38(24)23-10-4-3-5-11-23/h3-11,14-19H,1-2H3,(H2,31,35)(H,34,39)/t19-/m0/s1

2.1.3 InChI Key

XUMALORDVCFWKV-IBGZPJMESA-N

2.1.4 Canonical SMILES

CC(C1=CC2=C(C(=CC=C2)C#CC3=CN(N=C3)C)C(=O)N1C4=CC=CC=C4)NC(=O)C5=C6N=CC=CN6N=C5N

2.1.5 Isomeric SMILES

C[C@@H](C1=CC2=C(C(=CC=C2)C#CC3=CN(N=C3)C)C(=O)N1C4=CC=CC=C4)NC(=O)C5=C6N=CC=CN6N=C5N

2.2 Other Identifiers

2.2.1 UNII

FOF5155FMZ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-amino-n-((1s)-1-(8-((1-methyl-1h-pyrazol-4-yl)ethynyl)-1-oxo-2-phenyl-1,2-dihydro-3-isoquinolinyl)ethyl)pyrazolo(1,5-a)pyrimidine-3-carboxamide

2. Ipi-549

2.3.2 Depositor-Supplied Synonyms

1. Ipi-549

2. 1693758-51-8

3. Eganelisib [usan]

4. Pi3k-gamma Inhibitor Ipi-549

5. Fof5155fmz

6. Ipi549

7. Chembl3984425

8. 2-amino-n-[(1s)-1-[8-[2-(1-methylpyrazol-4-yl)ethynyl]-1-oxo-2-phenylisoquinolin-3-yl]ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

9. (s)-2-amino-n-(1-(8-((1-methyl-1h-pyrazol-4-yl)ethynyl)-1-oxo-2-phenyl-1,2- Dihydroisoquinolin-3-yl)ethyl)pyrazolo(1,5-a)pyrimidine-3-carboxamide

10. 2-amino-n-[(1s)-1-{8-[(1-methyl-1h-pyrazol-4-yl)ethynyl]-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl}ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

11. Pyrazolo(1,5-a)pyrimidine-3-carboxamide, 2-amino-n-((1s)-1-(1,2-dihydro-8-(2-(1-methyl-1h-pyrazol-4-yl)ethynyl)-1-oxo-2-phenyl-3-isoquinolinyl)ethyl)-

12. Pyrazolo[1,5-a]pyrimidine-3-carboxamide, 2-amino-n-[(1s)-1-[1,2-dihydro-8-[2-(1-methyl-1h-pyrazol-4-yl)ethynyl]-1-oxo-2-phenyl-3-isoquinolinyl]ethyl]-

13. Eganelisib [inn]

14. Unii-fof5155fmz

15. Eganelisib [who-dd]

16. Gtpl9563

17. Schembl16629991

18. Dtxsid301336580

19. Ipi-549(ipi549)

20. Amy16733

21. Ex-a1057

22. V7y

23. Bdbm50192880

24. Mfcd30533720

25. Nsc795067

26. Nsc801002

27. S8330

28. Who 11571

29. Zinc584906867

30. Ccg-269905

31. Cs-6106

32. Nsc-795067

33. Nsc-801002

34. Compound 26 [pmid: 27660692]

35. Ac-29898

36. As-55938

37. Hy-100716

38. A16332

39. 2-amino-n-((1s)-1-(8-((1-methyl-1h-pyrazol-4-yl)ethynyl)-1-oxo-2-phenyl-1,2-dihydro-3-isoquinolinyl)ethyl)pyrazolo(1,5-a)pyrimidine-3-carboxamide

40. 2-amino-n-[(1s)-1-{8-[2-(1-methyl-1h-pyrazol-4-yl)ethynyl]-1-oxo-2-phenyl- 1,2-dihydroisoquinolin-3-yl}ethyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

2.4 Create Date

2015-10-12

3 Chemical and Physical Properties

Molecular Formula	C₃₀H₂₄N₈O₂
Molecular Weight	528.6 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	528.20222204 g/mol
Monoisotopic Mass	528.20222204 g/mol
Topological Polar Surface Area	123 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	1060
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