Also known as: 1015474-32-4, Cc-122, 3-(5-amino-2-methyl-4-oxoquinazolin-3(4h)-yl)piperidine-2,6-dione, Cc122, Cc 122, Avadomide [usan]

Molecular Formula

C₁₄H₁₄N₄O₃

Molecular Weight

286.29 g/mol

InChI Key

RSNPAKAFCAAMBH-UHFFFAOYSA-N

FDA UNII

28DZS29F59

Avadomide is a novel, small molecule cereblon-modulating agent with potential antineoplastic, antiangiogenic and immunomodulatory activities. Upon oral administration, avadomide binds to and modulates cereblon to promote recruitment of the hematopoietic transcription factors Aiolos and Ikaros to the Cullin-4 RING E3 ubiquitin ligase complex. This binding results in the ubiquitination and rapid proteasomal degradation of Aiolos and Ikaros and the derepression of interferon (IFN)-stimulated genes, including DDX58 and IRF7, leading to apoptosis of certain tumor cells. Additionally, Aiolos degredation leads to derepression of the IL2 gene, thereby enhancing interleukin-2 production, costimulation of T-lymphocytes and IL-2-induced T-cell proliferation. Avadomide may also promote the activation of natural killer (NK) cells, potentially enhancing tumor cell killing. Aiolos and Ikaros are transcriptional repressors known to play an important role in normal B- and T-cell function.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-(5-amino-2-methyl-4-oxoquinazolin-3-yl)piperidine-2,6-dione

2.1.2 InChI

InChI=1S/C14H14N4O3/c1-7-16-9-4-2-3-8(15)12(9)14(21)18(7)10-5-6-11(19)17-13(10)20/h2-4,10H,5-6,15H2,1H3,(H,17,19,20)

2.1.3 InChI Key

RSNPAKAFCAAMBH-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=NC2=CC=CC(=C2C(=O)N1C3CCC(=O)NC3=O)N

2.2 Other Identifiers

2.2.1 UNII

28DZS29F59

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-(5-amino-2-methyl-4-oxoquinazolin-3(4h)-yl)piperidine-2,6-dione

2. Cc-122

2.3.2 Depositor-Supplied Synonyms

1. 1015474-32-4

2. Cc-122

3. 3-(5-amino-2-methyl-4-oxoquinazolin-3(4h)-yl)piperidine-2,6-dione

4. Cc122

5. Cc 122

6. Avadomide [usan]

7. Avadomide(cc-122)

8. 28dzs29f59

9. 3-(5-amino-2-methyl-4-oxoquinazolin-3-yl)piperidine-2,6-dione

10. 3-(5-amino-2-methyl-4-oxo-4h-quinazolin-3-yl)-piperidine-2,6-dione

11. 3-(5-amino-2-methyl-4-oxo-4h-quinazolin-3-yl)piperidine-2,6-dione

12. 2,6-piperidinedione, 3-(5-amino-2-methyl-4-oxo-3(4h)-quinazolinyl)-

13. 2,6-piperidinedione, 3-(5-amino-2-methyl-4-oxo-3(4h)-quinazolinyl)-;2,6-piperidinedione, 3-(5-amino-2-methyl-4-oxo-3(4h)-quinazolinyl)-

14. Cc-122avadomide

15. Avadomide [inn]

16. Avadomide (usan/inn)

17. Avadomide [who-dd]

18. Cc-112

19. Schembl282749

20. Unii-28dzs29f59

21. Us9694015, Compound A

22. Cc-122;cc 122;avadomide

23. Chembl3989934

24. Bdbm76986

25. Gtpl10522

26. Amy16366

27. Bcp15938

28. Ex-a1191

29. S7892

30. Ccg-267340

31. Cs-5995

32. Db14857

33. Sb18829

34. Compound A [wo2014039960a1]

35. Ac-33084

36. As-55858

37. Bp-27973

38. Db-112299

39. Hy-100507

40. C71075

41. D11132

42. A921203

43. 3-(5-amino-2-methy-4-oxo-4h-quinazolin-3-yl)-piperidine-2,6-dione

44. 3-(5-amino-2-methyl-4-oxoquinazolin-3 (4h)-yl)piperidine-2,6-dione

45. Rac-(3r)-3-(5-amino-2-methyl-4-oxoquinazolin-3(4h)-yl)piperidine-2,6-dione

2.4 Create Date

2008-10-20

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₁₄N₄O₃
Molecular Weight	286.29 g/mol
XLogP3	0
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	1
Exact Mass	286.10659032 g/mol
Monoisotopic Mass	286.10659032 g/mol
Topological Polar Surface Area	105 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	530
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Treatment of mature B-cell neoplasms

Avadomide

Avadomide

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