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Chemistry

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Also known as: 1357470-29-1, On123300, On-123300, Narazaciclib, Qj8ro3296g, Chembl3115681

Molecular Formula

C₂₄H₂₇N₇O

Molecular Weight

429.5 g/mol

InChI Key

VADOZMZXXRBXNY-UHFFFAOYSA-N

FDA UNII

QJ8RO3296G

Narazaciclib is an orally bioavailable inhibitor of NUAK family SNF1-like kinase 1 (AMPK-related protein kinase 5; ARK5), and the cyclin-dependent kinases 4 (CDK4) and 6 (CDK6), with potential antineoplastic activity. Upon oral administration,narazaciclib specifically binds to and inhibits ARK5, which interferes with the activation of ARK5-mediated signal transduction pathways and reduces cell proliferation in cancer cells that overexpress ARK5. In addition, ON 123300 inhibits CDK4 and 6 and prevents the phosphorylation of retinoblastoma (Rb) protein in early G1. Inhibition of Rb phosphorylation prevents CDK-mediated G1-S phase transition, which causes G1 phase cell cycle arrest, suppresses DNA synthesis and inhibits cancer cell growth. ARK5, a member of the AMP-activated protein kinase (AMPK) family, is associated with tumor growth and invasion. Overexpression of CDK4/6, which is seen in certain types of cancer, causes cell cycle deregulation.

1 2D Structure

Narazaciclib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

8-cyclopentyl-2-[4-(4-methylpiperazin-1-yl)anilino]-7-oxopyrido[2,3-d]pyrimidine-6-carbonitrile

2.1.2 InChI

InChI=1S/C24H27N7O/c1-29-10-12-30(13-11-29)20-8-6-19(7-9-20)27-24-26-16-18-14-17(15-25)23(32)31(22(18)28-24)21-4-2-3-5-21/h6-9,14,16,21H,2-5,10-13H2,1H3,(H,26,27,28)

2.1.3 InChI Key

VADOZMZXXRBXNY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1CCN(CC1)C2=CC=C(C=C2)NC3=NC=C4C=C(C(=O)N(C4=N3)C5CCCC5)C#N

2.2 Other Identifiers

2.2.1 UNII

QJ8RO3296G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. On123300

2.3.2 Depositor-Supplied Synonyms

1. 1357470-29-1

2. On123300

3. On-123300

4. Narazaciclib

5. Qj8ro3296g

6. Chembl3115681

7. Pyrido(2,3-d)pyrimidine-6-carbonitrile, 8-cyclopentyl-7,8-dihydro-2-((4-(4-methyl-1-piperazinyl)phenyl)amino)-7-oxo-

8. 8-cyclopentyl-2-[4-(4-methylpiperazin-1-yl)anilino]-7-oxopyrido[2,3-d]pyrimidine-6-carbonitrile

9. Unii-qj8ro3296g

10. On 123300

11. Narazaciclib [inn]

12. Schembl10050883

13. Gtpl11879

14. Bcp19186

15. Ex-a1111

16. Bdbm50447512

17. Mfcd28411414

18. Nsc802100

19. S8161

20. Akos030526450

21. Zinc103269269

22. Ccg-268995

23. Cs-5570

24. Nsc-802100

25. Sb16989

26. Compound 7x [pmid: 24417566]

27. Ac-35541

28. As-35286

29. Hy-12624

30. Db-100781

31. A857300

32. Q27287291

33. 8-cyclopentyl-2-((4-(4-methylpiperazin-1-yl)phenyl)amino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile;on 123300

34. 8-cyclopentyl-2-[4-(4-methyl-piperazine-1-yl)-phenylamino]-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile

2.4 Create Date

2012-03-02

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₂₇N₇O
Molecular Weight	429.5 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	429.22770851 g/mol
Monoisotopic Mass	429.22770851 g/mol
Topological Polar Surface Area	88.4 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	754
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