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Also known as: Edo-s101, 1236199-60-2, Minomustine, Edo-s 101, Edo-s-101, Tinostamustine [usan]

Molecular Formula

C₁₉H₂₈Cl₂N₄O₂

Molecular Weight

415.4 g/mol

InChI Key

GISXTRIGVCKQBX-UHFFFAOYSA-N

FDA UNII

29DKI2H2NY

Tinostamustine is an alkylating histone-deacetylase inhibitor (HDACi) fusion molecule composed of the alkylating agent bendamustine fused to the pan-HDACi vorinostat, with potential bi-functional antineoplastic activity. Upon administration of tinostamustine the vorinostat moiety targets and binds to HDACs. This leads to an accumulation of highly acetylated histones, which results in an induction of chromatin remodeling, a modulation of gene expression, an inhibition of tumor cell division and the induction of tumor cell apoptosis. The bendamustine moiety binds to, alkylates and crosslinks macromolecules, inhibiting DNA, RNA and protein synthesis, which also results in tumor cell apoptosis. Thus, tinostamustine shows superior efficacy compared to the activity of either agent alone. In addition, the inhibition of HDAC6 activity by tinostamustine induces the activation of inositol-requiring enzyme 1 (IRE-1), the key regulatory protein for the unfolded protein response (UPR). Induction of the UPR increases the sensitivity of certain cancer cell types to certain chemotherapeutic agents, such as proteasome inhibitors. Therefore, tinostamustine may work synergistically with proteasome inhibitors. HDACs, enzymes that deacetylate chromatin histone proteins, are overexpressed in various cancers and play a key role in proliferation and resistance of tumor cells.

1 2D Structure

Tinostamustine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

7-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]-N-hydroxyheptanamide

2.1.2 InChI

InChI=1S/C19H28Cl2N4O2/c1-24-17-9-8-15(25(12-10-20)13-11-21)14-16(17)22-18(24)6-4-2-3-5-7-19(26)23-27/h8-9,14,27H,2-7,10-13H2,1H3,(H,23,26)

2.1.3 InChI Key

GISXTRIGVCKQBX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1C2=C(C=C(C=C2)N(CCCl)CCCl)N=C1CCCCCCC(=O)NO

2.2 Other Identifiers

2.2.1 UNII

29DKI2H2NY

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Edo-s101

2.3.2 Depositor-Supplied Synonyms

1. Edo-s101

2. 1236199-60-2

3. Minomustine

4. Edo-s 101

5. Edo-s-101

6. Tinostamustine [usan]

7. Tinostamustine(edo-s101)

8. 29dki2h2ny

9. 7-(5-(bis(2-chloroethyl)amino)-1-methyl-1h-benzo[d]imidazol-2-yl)-n-hydroxyheptanamide

10. 7-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]-n-hydroxyheptanamide

11. 1h-benzimidazole-2-heptanamide, 5-[bis(2-chloroethyl)amino]-n-hydroxy-1-methyl-

12. 1h-benzimidazole-2-heptanamide, 5-(bis(2-chloroethyl)amino)-n-hydroxy-1-methyl-

13. Starbld0018955

14. Unii-29dki2h2ny

15. Tinostamustine (usan/inn)

16. Tinostamustine [inn]

17. Schembl7915449

18. Tinostamustine [who-dd]

19. Chembl3989941

20. Bcp20331

21. Ex-a1322

22. Bdbm50569838

23. Zinc68244536

24. Cs-6484

25. Db15147

26. Sb19172

27. Be170657

28. Hy-101780

29. S8769

30. D11182

31. E76854

32. 7-(5-(bis(2-chloroethyl)amino)-1-methyl-1h-benzimidazol-2-yl)-n-hydroxyheptanamide

2.4 Create Date

2010-08-09

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₈Cl₂N₄O₂
Molecular Weight	415.4 g/mol
XLogP3	3.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	12
Exact Mass	414.1589315 g/mol
Monoisotopic Mass	414.1589315 g/mol
Topological Polar Surface Area	70.4 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	438
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