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Also known as: Azd-5153, Azd5153, 1869912-39-9, C7c7u6yeao, Chembl4078100, Azd 5153 [who-dd]

Molecular Formula

C₂₅H₃₃N₇O₃

Molecular Weight

479.6 g/mol

InChI Key

RSMYFSPOTCDHHJ-GOSISDBHSA-N

FDA UNII

C7C7U6YEAO

Bivalent BRD4 Inhibitor AZD5153 is an orally bioavailable bivalent inhibitor of bromodomain-containing protein 4 (BRD4), with potential antineoplastic activity. Upon oral administration, the BRD4 inhibitor AZD5153 selectively binds to the acetylated lysine recognition motifs in two bromodomains in the BRD4 protein, thereby preventing the binding of BRD4 to acetylated lysines on histones. This disrupts chromatin remodeling and dysregulates expression of target genes, which leads to the downregulation of the expression of certain growth-promoting genes, induces apoptosis and inhibits the proliferation of BRD4-overexpressing tumor cells. BRD4, a member of the human bromodomain and extra-terminal (BET) family of proteins, is a transcriptional regulator that is overexpressed in certain tumor cells and plays an important role in cellular proliferation.

1 2D Structure

AZD5153

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3R)-4-[2-[4-[1-(3-methoxy-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl]phenoxy]ethyl]-1,3-dimethylpiperazin-2-one

2.1.2 InChI

InChI=1S/C25H33N7O3/c1-18-24(33)29(2)14-15-30(18)16-17-35-21-6-4-19(5-7-21)20-10-12-31(13-11-20)23-9-8-22-26-27-25(34-3)32(22)28-23/h4-9,18,20H,10-17H2,1-3H3/t18-/m1/s1

2.1.3 InChI Key

RSMYFSPOTCDHHJ-GOSISDBHSA-N

2.1.4 Canonical SMILES

CC1C(=O)N(CCN1CCOC2=CC=C(C=C2)C3CCN(CC3)C4=NN5C(=NN=C5OC)C=C4)C

2.1.5 Isomeric SMILES

C[C@@H]1C(=O)N(CCN1CCOC2=CC=C(C=C2)C3CCN(CC3)C4=NN5C(=NN=C5OC)C=C4)C

2.2 Other Identifiers

2.2.1 UNII

C7C7U6YEAO

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-(2-(4-(1-(3-methoxy-(1,2,4)triazolo(4,3-b)pyridazin-6-yl)-4-piperidyl)phenoxy)ethyl)-1,3-dimethylpiperazin-2-one

2. Azd 5153

3. Azd-5153

4. Azd5153

2.3.2 Depositor-Supplied Synonyms

1. Azd-5153

2. Azd5153

3. 1869912-39-9

4. C7c7u6yeao

5. Chembl4078100

6. Azd 5153 [who-dd]

7. Azd 5153

8. 1869912-39-9 (free Base)

9. (r)-4-(2-(4-(1-(3-methoxy-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl)phenoxy)ethyl)-1,3-dimethylpiperazin-2-one

10. 2-piperazinone, 4-(2-(4-(1-(3-methoxy-1,2,4-triazolo(4,3-b)pyridazin-6-yl)-4-piperidinyl)phenoxy)ethyl)-1,3-dimethyl-, (3r)-

11. Unii-c7c7u6yeao

12. Schembl17477306

13. Amy16812

14. Bcp20057

15. Ex-a1317

16. Azd5153, 6-hydroxy-2-naphthoate

17. Bdbm50260093

18. Mfcd30530420

19. Nsc797938

20. Akos030627661

21. Azd-5153, 6-hydroxy-2-naphthoate

22. Zinc575441177

23. Nsc-797938

24. Ac-31599

25. As-35242

26. J3.544.368a

27. Q27467599

28. (3r)-4-[2-[4-[1-(3-methoxy-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-4-piperidyl]phenoxy]ethyl]-1,3-dimethyl-piperazin-2-one

29. (3r)-4-[2-[4-[1-(3-methoxy-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperidin-4-yl]phenoxy]ethyl]-1,3-dimethylpiperazin-2-one

30. Xnh

2.4 Create Date

2016-02-23

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₃₃N₇O₃
Molecular Weight	479.6 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Exact Mass	479.26448794 g/mol
Monoisotopic Mass	479.26448794 g/mol
Topological Polar Surface Area	88.3 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	699
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