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Also known as: 1000023-04-0, Voruciclib [inn], P1446a-05, W66xp666am, 2-[2-chloro-4-(trifluoromethyl)phenyl]-5,7-dihydroxy-8-[(2r,3s)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl]chromen-4-one, Chembl3905910

Molecular Formula

C₂₂H₁₉ClF₃NO₅

Molecular Weight

469.8 g/mol

InChI Key

MRPGRAKIAJJGMM-OCCSQVGLSA-N

FDA UNII

W66XP666AM

Voruciclib is a cyclin-dependent kinase (CDK) inhibitor with potential antineoplastic activity. Upon administration, voruciclib selectively inhibits cyclin-dependent kinase 4 (CDK4) and 6 (CDK6). This inhibits retinoblastoma (Rb) protein phosphorylation early in the G1 phase, which prevents CDK-mediated G1-S phase transition and leads to cell cycle arrest. This suppresses DNA replication and decreases tumor cell proliferation. CDK4 and 6 are serine/threonine kinases that are upregulated in many tumor cell types and play a key role in the regulation of cell cycle progression.

1 2D Structure

Voruciclib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[2-chloro-4-(trifluoromethyl)phenyl]-5,7-dihydroxy-8-[(2R,3S)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl]chromen-4-one

2.1.2 InChI

InChI=1S/C22H19ClF3NO5/c1-27-5-4-12(14(27)9-28)19-15(29)7-16(30)20-17(31)8-18(32-21(19)20)11-3-2-10(6-13(11)23)22(24,25)26/h2-3,6-8,12,14,28-30H,4-5,9H2,1H3/t12-,14+/m1/s1

2.1.3 InChI Key

MRPGRAKIAJJGMM-OCCSQVGLSA-N

2.1.4 Canonical SMILES

CN1CCC(C1CO)C2=C(C=C(C3=C2OC(=CC3=O)C4=C(C=C(C=C4)C(F)(F)F)Cl)O)O

2.1.5 Isomeric SMILES

CN1CC[C@H]([C@@H]1CO)C2=C(C=C(C3=C2OC(=CC3=O)C4=C(C=C(C=C4)C(F)(F)F)Cl)O)O

2.2 Other Identifiers

2.2.1 UNII

W66XP666AM

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(2-chloro-4-(trifluoromethyl) Phenyl)-5, 7-dihydroxy-8-((2r, 3s)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl)-4h-1-benzopyran-4-one

2.3.2 Depositor-Supplied Synonyms

1. 1000023-04-0

2. Voruciclib [inn]

3. P1446a-05

4. W66xp666am

5. 2-[2-chloro-4-(trifluoromethyl)phenyl]-5,7-dihydroxy-8-[(2r,3s)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl]chromen-4-one

6. Chembl3905910

7. 2-(2-chloro-4-(trifluoromethyl)phenyl)-5,7-dihydroxy-8-((2r,3s)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl)-4h-1-benzopyran-4-one

8. 4h-1-benzopyran-4-one, 2-(2-chloro-4-(trifluoromethyl)phenyl)-5,7-dihydroxy-8-((2r,3s)-2-(hydroxymethyl)-1-methyl-3-pyrrolidinyl)-

9. Unii-w66xp666am

10. Voruciclib [who-dd]

11. Gtpl9923

12. Schembl3108205

13. Ex-a1056

14. Bdbm50193104

15. Nsc784284

16. P1446a

17. Db15157

18. Nsc-784284

19. Ncgc00387877-01

20. Ac-31553

21. As-82346

22. Hy-12422

23. Cs-0011273

24. Q27292377

25. 2-(2-chloro-4-(trifluoromethyl)phenyl)-5,7-dihydroxy-8-((2r,3s)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl)-4h-chromen-4-one

26. 2-[2-chloro-4-(trifluoromethyl)phenyl]-5,7-dihydroxy-8-[(2r,3s)-2-(hydroxymethyl)-1-methyl-3-pyrrolidinyl]-4h-1-benzopyran-4-one

2.4 Create Date

2012-11-30

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₁₉ClF₃NO₅
Molecular Weight	469.8 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	3
Exact Mass	469.0903849 g/mol
Monoisotopic Mass	469.0903849 g/mol
Topological Polar Surface Area	90.2 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	750
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