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Also known as: Ch5132799, 1007207-67-1, Ch-5132799, Ch 5132799, Izorlisib, Chembl1684984

Molecular Formula

C₁₅H₁₉N₇O₃S

Molecular Weight

377.4 g/mol

InChI Key

JEGHXKRHKHPBJD-UHFFFAOYSA-N

FDA UNII

JCL936W835

Izorlisib is an orally bioavailable inhibitor of the class I phosphatidylinositol-4,5-bisphosphate 3-kinase (PI3K) catalytic subunit alpha (PIK3CA), with potential antineoplastic activity. Upon administration, izorlisib selectively binds to and inhibits PIK3CA and its mutated forms in the PI3K/Akt (protein kinase B)/mammalian target of rapamycin (mTOR) pathway. This results in both apoptosis and growth inhibition in PIK3CA-expressing tumor cells. By specifically targeting PIK3CA, izorlisib may be more efficacious and less toxic than pan-PI3K inhibitors. In addition, izorlisib also targets mutated forms of PI3K gamma (PI3Kg). It may also stimulate the immune system to restore CD8+ T-cell activation and cytotoxicity. Dysregulation of the PI3K/Akt/mTOR pathway is often found in solid tumors and results in the promotion of tumor cell growth, survival, and resistance to chemo- and radio-therapy. PIK3CA, one of the most frequently mutated oncogenes, encodes the p110-alpha catalytic subunit of the class I PI3K. In most solid tumors, the activation of the PI3K pathway is induced by mutations of PIK3CA.

1 2D Structure

MEN1611

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-(7-methylsulfonyl-2-morpholin-4-yl-5,6-dihydropyrrolo[2,3-d]pyrimidin-4-yl)pyrimidin-2-amine

2.1.2 InChI

InChI=1S/C15H19N7O3S/c1-26(23,24)22-3-2-11-12(10-8-17-14(16)18-9-10)19-15(20-13(11)22)21-4-6-25-7-5-21/h8-9H,2-7H2,1H3,(H2,16,17,18)

2.1.3 InChI Key

JEGHXKRHKHPBJD-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CS(=O)(=O)N1CCC2=C(N=C(N=C21)N3CCOCC3)C4=CN=C(N=C4)N

2.2 Other Identifiers

2.2.1 UNII

JCL936W835

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ch 5132799

2. Ch-5132799

3. Ch5132799

2.3.2 Depositor-Supplied Synonyms

1. Ch5132799

2. 1007207-67-1

3. Ch-5132799

4. Ch 5132799

5. Izorlisib

6. Chembl1684984

7. Ch5132799 (pa-799)

8. Jcl936w835

9. Pa799

10. Pa-799

11. 5-(7-methanesulfonyl-2-morpholin-4-yl-6,7-dihydro-5h-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-ylamine

12. (5-(7-methylsulfonyl-2-(morpholin-4-yl)-6,7-dihydro-5h-pyrrolo(2,3-d)pyrimidin-4-yl)pyrimidin-2-yl)amine

13. Unii-jcl936w835

14. 5-(7-methylsulfonyl-2-morpholin-4-yl-5,6-dihydropyrrolo[2,3-d]pyrimidin-4-yl)pyrimidin-2-amine

15. Izorlisib [inn]

16. Mls006010989

17. Gtpl7743

18. Schembl2377154

19. Dtxsid40678540

20. Ex-a997

21. Men1611

22. Hms3656h15

23. Hms3750i19

24. Bcp02894

25. Men-1611

26. Bdbm50338197

27. Mfcd22419020

28. Nsc762382

29. Nsc800984

30. S2699

31. Zinc66074200

32. Akos025404886

33. Bcp9000513

34. Ccg-264982

35. Cs-0981

36. Db13051

37. Nsc-762382

38. Nsc-800984

39. Sb20410

40. Ncgc00346650-01

41. Ncgc00346650-06

42. 5-[7-(methanesulfonyl)-2-(morpholin-4-yl)-6,7-dihydro-5h-pyrrolo[2,3-d]pyrimidin-4-yl]pyrimidin-2-amine

43. Ac-28422

44. As-16285

45. Hy-15466

46. Smr004702790

47. Bcp0726000261

48. Sw220190-1

49. J-000203

50. Q27075949

51. 2-pyrimidinamine, 5-[6,7-dihydro-7-(methylsulfonyl)-2-(4-morpholinyl)-5h-pyrrolo[2,3-d]pyrimidin-4-yl]-

52. 5-[7-(methylsulfonyl)-2-(morpholin-4-yl)-6,7-dihydro-5h-pyrrolo[2,3-d]pyrimidin-4-yl]pyrimidin-2-amine

53. 5-[7-methanesulfonyl-2-(morpholin-4-yl)-5h,6h,7h-pyrrolo[2,3-d]pyrimidin-4-yl]pyrimidin-2-amine

2.4 Create Date

2010-12-06

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₉N₇O₃S
Molecular Weight	377.4 g/mol
XLogP3	-0.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	3
Exact Mass	377.12700867 g/mol
Monoisotopic Mass	377.12700867 g/mol
Topological Polar Surface Area	136 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	587
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