Also known as: Azd4635, 1321514-06-0, Imaradenant, Azd-4635, Htl-1071, Htl1071

Molecular Formula

C₁₅H₁₁ClFN₅

Molecular Weight

315.73 g/mol

InChI Key

NCWQLHHDGDXIJN-UHFFFAOYSA-N

FDA UNII

770140J08A

Imaradenant is an orally bioavailable antagonist of the adenosine A2A receptor (A2AR; ADORA2A), with potential immunomodulating and antineoplastic activities. Upon administration, imaradenant selectively binds to and inhibits A2AR expressed on T-lymphocytes. This blocks tumor-released adenosine from interacting with A2AR and prevents the adenosine/A2AR-mediated inhibition of T-lymphocytes. This results in the proliferation and activation of T-lymphocytes, and stimulates a T-cell-mediated immune response against tumor cells. A2AR, a G protein-coupled receptor, is highly expressed on the cell surfaces of T-cells and, upon activation by adenosine, inhibits T-cell proliferation and activation. Adenosine is often overproduced by cancer cells and plays a key role in immunosuppression.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

6-(2-chloro-6-methylpyridin-4-yl)-5-(4-fluorophenyl)-1,2,4-triazin-3-amine

2.1.2 InChI

InChI=1S/C15H11ClFN5/c1-8-6-10(7-12(16)19-8)14-13(20-15(18)22-21-14)9-2-4-11(17)5-3-9/h2-7H,1H3,(H2,18,20,22)

2.1.3 InChI Key

NCWQLHHDGDXIJN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC(=CC(=N1)Cl)C2=C(N=C(N=N2)N)C3=CC=C(C=C3)F

2.2 Other Identifiers

2.2.1 UNII

770140J08A

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Azd4635

2. 1321514-06-0

3. Imaradenant

4. Azd-4635

5. Htl-1071

6. Htl1071

7. Imaradenant [inn]

8. Azd 4635

9. 770140j08a

10. 1,2,4-triazin-3-amine, 6-(2-chloro-6-methyl-4-pyridinyl)-5-(4-fluorophenyl)-

11. 6-(2-chloranyl-6-methyl-pyridin-4-yl)-5-(4-fluorophenyl)-1,2,4-triazin-3-amine

12. Imaradenant [who-dd]

13. Schembl2320714

14. Chembl4594442

15. Gtpl11153

16. Azd 4635 [who-dd]

17. Bdbm493757

18. Unii-770140j08a

19. Amy16806

20. Bcp25990

21. Ex-a1681

22. Nsc802101

23. Us10988455, Example 1(xcv)

24. Akos037515559

25. Azd4635 (htl1071)

26. Nsc-802101

27. Ac-30333

28. Bs-15183

29. Hy-101980

30. Cs-0022379

31. S8720

32. A16820

33. C72299

34. A902721

35. 5-(4-fluorophenyl)-6-(2-chloro-6-methyl-pyridin-4-yl)-1,2,4-triazin-3-amine

36. F9q

2.4 Create Date

2015-02-02

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₁ClFN₅
Molecular Weight	315.73 g/mol
XLogP3	2.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	315.0687012 g/mol
Monoisotopic Mass	315.0687012 g/mol
Topological Polar Surface Area	77.6 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	366
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

AZD4635

AZD4635

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