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Also known as: Ab928, 2239273-34-6, Ab-928, Etrumadenant, 3-(2-amino-6-(1-((6-(2-hydroxypropan-2-yl)pyridin-2-yl)methyl)-1h-1,2,3-triazol-4-yl)pyrimidin-4-yl)-2-methylbenzonitrile, Etrumadenant [usan]

Molecular Formula

C₂₃H₂₂N₈O

Molecular Weight

426.5 g/mol

InChI Key

BUXIAWLTBSXYSW-UHFFFAOYSA-N

FDA UNII

W0ZE0NT8IF

Etrumadenant is an orally bioavailable antagonist of both the immunomodulatory checkpoint molecules adenosine A2A receptor (A2AR; ADORA2A) and A2B receptor (A2BR; ADORA2B), with potential immunomodulating and antineoplastic activities. Upon administration, etrumadenant competes with tumor-released adenosine for binding to A2AR and A2BR expressed on numerous intra-tumoral immune cells, such as dendritic cells (DCs), natural killer (NK) cells, macrophages and T-lymphocytes. The binding of AB928 to A2AR and A2BR inhibits A2AR/A2BR activity and prevents adenosine-A2AR/A2BR-mediated signaling. A2AR/A2BR inhibition activates and enhances the proliferation of various immune cells, abrogates the adenosine-mediated immunosuppression in the tumor microenvironment (TME) and activates the immune system to exert anti-tumor immune responses against cancer cells, which leads to tumor cell killing. A2AR and A2BR, G protein-coupled signaling receptors, are expressed on the cell surfaces of numerous immune cells. Adenosine is often overproduced by tumor cells and plays a key role in immunosuppression and tumor cell proliferation.

1 2D Structure

Etrumadenant

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[2-amino-6-[1-[[6-(2-hydroxypropan-2-yl)pyridin-2-yl]methyl]triazol-4-yl]pyrimidin-4-yl]-2-methylbenzonitrile

2.1.2 InChI

InChI=1S/C23H22N8O/c1-14-15(11-24)6-4-8-17(14)18-10-19(28-22(25)27-18)20-13-31(30-29-20)12-16-7-5-9-21(26-16)23(2,3)32/h4-10,13,32H,12H2,1-3H3,(H2,25,27,28)

2.1.3 InChI Key

BUXIAWLTBSXYSW-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(C=CC=C1C2=CC(=NC(=N2)N)C3=CN(N=N3)CC4=NC(=CC=C4)C(C)(C)O)C#N

2.2 Other Identifiers

2.2.1 UNII

W0ZE0NT8IF

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Ab928

2. 2239273-34-6

3. Ab-928

4. Etrumadenant

5. 3-(2-amino-6-(1-((6-(2-hydroxypropan-2-yl)pyridin-2-yl)methyl)-1h-1,2,3-triazol-4-yl)pyrimidin-4-yl)-2-methylbenzonitrile

6. Etrumadenant [usan]

7. W0ze0nt8if

8. 3-[2-amino-6-[1-[[6-(1-hydroxy-1-methylethyl)-2-pyridinyl]methyl]-1h-1,2,3-triazol-4-yl]-4-pyrimidinyl]-2-methylbenzonitrile

9. Trumadenant

10. Unii-w0ze0nt8if

11. A2ar/a2br Antagonist-1

12. Etrumadenant [inn]

13. Etrumadenant [who-dd]

14. Chembl4740383

15. Schembl20401465

16. Gtpl11154

17. Bcp33220

18. Ex-a3172

19. Mfcd32263040

20. Nsc823658

21. S9608

22. Who 11620

23. Zb1610

24. Akos037649091

25. Ab928 ; Ab 928

26. Nsc-823658

27. Ac-36346

28. Bs-16547

29. Hy-129393

30. Cs-0105184

31. D81385

32. Q66977586

33. Benzonitrile, 3-[2-amino-6-[1-[[6-(1-hydroxy-1-methylethyl)-2-pyridinyl]methyl]-1h-1,2,3-triazol-4-yl]-4-pyrimidinyl]-2-methyl-

2.4 Create Date

2018-12-15

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₂N₈O
Molecular Weight	426.5 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Exact Mass	426.19165736 g/mol
Monoisotopic Mass	426.19165736 g/mol
Topological Polar Surface Area	139 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	680
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