Also known as: Kb-0742, 2416873-83-9, Chembl5199065, Kb0742, Istisociclib (usan), Istisociclib [usan]

Molecular Formula

C₁₆H₂₅N₅

Molecular Weight

287.40 g/mol

InChI Key

VYKCLMALANGCDF-STQMWFEESA-N

FDA UNII

F7J6KSY5I8

Istisociclib is an orally bioavailable, selective inhibitor of the serine/threonine cyclin-dependent kinase 9 (CDK9), the catalytic subunit of the RNA polymerase II (RNA Pol II) elongation factor positive transcription elongation factor b (PTEF-b; PTEFb), with potential antineoplastic activity. Upon oral administration, istisociclib targets, binds to and blocks the phosphorylation and kinase activity of CDK9, thereby preventing PTEFb-mediated activation of RNA Pol II, leading to the inhibition of gene transcription of various anti-apoptotic proteins and oncogenic transcription factors including MYC and androgen receptor (AR). This induces cell cycle arrest and apoptosis and prevents tumor cell proliferation. CDK9 regulates elongation of transcription through phosphorylation of RNA Pol II at serine 2 (p-Ser2-RNAPII), and is an important cofactor for various oncogenic transcription factors. It is upregulated in various tumor cell types and plays a key role in the regulation of Pol II-mediated transcription of anti-apoptotic proteins. Tumor cells are dependent on anti-apoptotic proteins for their survival.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S,3S)-3-N-(5-pentan-3-ylpyrazolo[1,5-a]pyrimidin-7-yl)cyclopentane-1,3-diamine

2.1.2 InChI

InChI=1S/C16H25N5/c1-3-11(4-2)14-10-16(19-13-6-5-12(17)9-13)21-15(20-14)7-8-18-21/h7-8,10-13,19H,3-6,9,17H2,1-2H3/t12-,13-/m0/s1

2.1.3 InChI Key

VYKCLMALANGCDF-STQMWFEESA-N

2.2 Other Identifiers

2.2.1 UNII

F7J6KSY5I8

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Kb-0742

2. 2416873-83-9

3. Chembl5199065

4. Kb0742

5. Istisociclib (usan)

6. Istisociclib [usan]

7. (1s,3s)-3-n-(5-pentan-3-ylpyrazolo[1,5-a]pyrimidin-7-yl)cyclopentane-1,3-diamine

8. (1s,3s)-n1-(5-(pentan-3-yl)pyrazolo[1,5-a]pyrimidin-7-yl)cyclopentane-1,3-diamine

9. Istisociclib [inn]

10. F7j6ksy5i8

11. Kb0742 2hcl

12. Orb1089900

13. Kb-0742 Hcl?

14. Schembl21877722

15. Gtpl13068

16. Ex-a6433

17. Bdbm50593922

18. Nsc834161

19. Nsc-834161

20. Compound 28 [pmid: 37967851]

21. Ub-18422

22. Hy-137478

23. Kb-130742

24. Cs-0139025

25. Kb-00130742

26. D12868

27. (1s,3s)-3-amino-1-[5-(1-ethylpropyl)-1,4,7a-triazainden-7-ylamino]cyclopentane

28. (1s,3s)-n1-[5-(1-ethylpropyl)pyrazolo[1,5-a]pyrimidin-7-yl]-1,3-cyclopentanediamine

29. 1,3-cyclopentanediamine, N1-[5-(1-ethylpropyl)pyrazolo[1,5-a]pyrimidin-7-yl]-, (1s,3s)-

2.4 Create Date

2020-06-27

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₅N₅
Molecular Weight	287.40 g/mol
XLogP3	2.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	68.2
Heavy Atom Count	21
Formal Charge	0
Complexity	333
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

Istisociclib

Istisociclib

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