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Also known as: 2098191-53-6, Eft226, Eft-226, Zotatifin [inn], Zotatifin [usan], 2ewn8z05cn

Molecular Formula

C₂₈H₂₉N₃O₅

Molecular Weight

487.5 g/mol

InChI Key

QYCXWOACFWMQFO-WZWZCULESA-N

FDA UNII

2EWN8Z05CN

Zotatifin is a selective inhibitor of the eukaryotic translation initiation factor 4A (eIF4A), with potential antineoplastic activity. Upon administration of zotatifin, this agent targets and binds to elF4A, and promotes eIF4A binding to mRNA with specific polypurine motifs within their 5'-untranslated region (5'-UTR), leading to the formation of a stable sequence-specific ternary complex with eIF4A and mRNA (elF4A- zotatifin-mRNA). This results in the translational repression of key oncogenes and anti-apoptotic proteins involved in tumor cell proliferation, survival and metastasis, such as KRAS, Myc, myeloid cell leukemia-1 (Mcl-1), B-cell lymphoma 2 (Bcl-2), cyclin-dependent kinase (CDK) 4 and 6, cyclin D, fibroblast growth factor receptor (FGFR) 1 and 2, human epidermal growth factor receptor 2 (HER2; ERBB2), and beta-catenin. The inhibition of the expression of these oncogenes leads to the inhibition of various oncogenic signal transduction pathways. This inhibits proliferation and induces apoptosis in tumor cells. eIF4A, a RNA helicase and the rate-limiting component of the eukaryotic translation initiation complex, catalyzes the ATP-dependent unwinding of RNA duplexes and facilitates 43S ribosome scanning within the 5'-UTR. elF4A is activated by various oncogenic signaling pathways, including RAS/mitogen-activated protein kinase (MAPK) and phosphatidylinositide 3-kinase (PI3K)/AKT pathways, and regulates the translation of oncogenes and tumor survival factors with complex secondary structures within the 5'-UTRs that are required for tumor cell proliferation, survival and metastasis.

1 2D Structure

Zotatifin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[(2S,3R,4S,5S,6R)-4-[(dimethylamino)methyl]-2,3-dihydroxy-10,12-dimethoxy-5-phenyl-7-oxa-11-azatricyclo[6.4.0.02,6]dodeca-1(12),8,10-trien-6-yl]benzonitrile

2.1.2 InChI

InChI=1S/C28H29N3O5/c1-31(2)16-20-23(18-8-6-5-7-9-18)28(19-12-10-17(15-29)11-13-19)27(33,25(20)32)24-21(36-28)14-22(34-3)30-26(24)35-4/h5-14,20,23,25,32-33H,16H2,1-4H3/t20-,23-,25-,27+,28+/m1/s1

2.1.3 InChI Key

QYCXWOACFWMQFO-WZWZCULESA-N

2.1.4 Canonical SMILES

CN(C)CC1C(C2(C(C1O)(C3=C(N=C(C=C3O2)OC)OC)O)C4=CC=C(C=C4)C#N)C5=CC=CC=C5

2.1.5 Isomeric SMILES

CN(C)C[C@@H]1[C@H]([C@]2([C@@]([C@@H]1O)(C3=C(N=C(C=C3O2)OC)OC)O)C4=CC=C(C=C4)C#N)C5=CC=CC=C5

2.2 Other Identifiers

2.2.1 UNII

2EWN8Z05CN

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 2098191-53-6

2. Eft226

3. Eft-226

4. Zotatifin [inn]

5. Zotatifin [usan]

6. 2ewn8z05cn

7. 4-((5ar,6s,7s,8r,8as)-7-((dimethylamino)methyl)-8,8a-dihydroxy-1,3-dimethoxy-6-phenyl-6,7,8,8a-tetrahydro-5ah-cyclopenta[4,5]furo[3,2-c]pyridin-5a-yl)benzonitrile

8. 4-((5ar,6s,7s,8r,8as)-7-((dimethylamino)methyl)-8,8a-dihydroxy-1,3-dimethoxy-6-phenyl-6,7,8,8a-tetrahydro-5ah-cyclopenta(4,5)furo(3,2-c)pyridin-5a-yl)benzonitrile

9. Benzonitrile, 4-((5ar,6s,7s,8r,8as)-7-((dimethylamino)methyl)-6,7,8,8a-tetrahydro-8,8a-dihydroxy-1,3-dimethoxy-6-phenyl-5ah-cyclopenta(4,5)furo(3,2-c)pyridin-5a-yl)-

10. Zotafin

11. Rel-zotatifin

12. Zotatifin (usan/inn)

13. Unii-2ewn8z05cn

14. Zotatifin [who-dd]

15. Chembl4303782

16. Schembl18864788

17. Dtxsid001022536

18. Ex-a4623

19. Bdbm50540861

20. Nsc818001

21. Nsc828584

22. Who 10998

23. Nsc-818001

24. Nsc-828584

25. Hy-112163

26. Cs-0043584

27. D11837

28. A937238

29. 4-[(2s,3r,4s,5s,6r)-4-[(dimethylamino)methyl]-2,3-dihydroxy-10,12-dimethoxy-5-phenyl-7-oxa-11-azatricyclo[6.4.0.02,6]dodeca-1(12),8,10-trien-6-yl]benzonitrile

2.4 Create Date

2017-08-04

3 Chemical and Physical Properties

Molecular Formula	C₂₈H₂₉N₃O₅
Molecular Weight	487.5 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	6
Exact Mass	487.21072103 g/mol
Monoisotopic Mass	487.21072103 g/mol
Topological Polar Surface Area	108 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	819
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1