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Also known as: Mpt0e028, 1338320-94-7, T65l58fi65, (e)-3-[1-(benzenesulfonyl)-2,3-dihydroindol-5-yl]-n-hydroxyprop-2-enamide, 2-propenamide, 3-(2,3-dihydro-1-(phenylsulfonyl)-1h-indol-5-yl)-n-hydroxy-, Imofinostat

Molecular Formula

C₁₇H₁₆N₂O₄S

Molecular Weight

344.4 g/mol

InChI Key

MGTIFSBCGGAZDB-VQHVLOKHSA-N

FDA UNII

T65L58FI65

Imofinostat is an orally bioavailable N-hydroxyacrylamide-derived inhibitor of both human pan-histone deacetylase (HDAC) enzymes and the serine/threonine protein kinase Akt (protein kinase B), with potential antineoplastic activity. Upon administration, imofinostat selectively binds to and inhibits HDACs, which inhibits deacetylation of histone proteins and leads to the accumulation of highly acetylated histones. This may result in both an induction of chromatin remodeling, and the selective transcription of tumor suppressor genes. This prevents cell division and induces both cell cycle arrest and apoptosis, which may inhibit the proliferation of susceptible tumor cells. In addition, imofinostat inhibits the phosphorylation and activation of Akt, which prevents the activation of downstream signaling pathways, independent of its HDAC inhibitory activity. HDACs, upregulated in many tumor cell types, are a family of enzymes that deacetylate histone proteins. Akt, overexpressed in many tumor cell types, plays a key role in tumor cell proliferation and survival.

1 2D Structure

Imofinostat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(E)-3-[1-(benzenesulfonyl)-2,3-dihydroindol-5-yl]-N-hydroxyprop-2-enamide

2.1.2 InChI

InChI=1S/C17H16N2O4S/c20-17(18-21)9-7-13-6-8-16-14(12-13)10-11-19(16)24(22,23)15-4-2-1-3-5-15/h1-9,12,21H,10-11H2,(H,18,20)/b9-7+

2.1.3 InChI Key

MGTIFSBCGGAZDB-VQHVLOKHSA-N

2.2 Other Identifiers

2.2.1 UNII

T65L58FI65

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Mpt0e028

2. 1338320-94-7

3. T65l58fi65

4. (e)-3-[1-(benzenesulfonyl)-2,3-dihydroindol-5-yl]-n-hydroxyprop-2-enamide

5. 2-propenamide, 3-(2,3-dihydro-1-(phenylsulfonyl)-1h-indol-5-yl)-n-hydroxy-

6. Imofinostat

7. Unii-t65l58fi65

8. Imofinostat [inn]

9. Orb1706952

10. Schembl2511433

11. Mgtifsbcggazdb-vqhvlokhsa-n

12. Glxc-04031

13. Akos040742169

14. Ms-25283

15. Sy461501

16. Hy-124295

17. Cs-0086144

18. G16985

19. Q27289720

20. (e)-n-hydroxy-3-[1-(phenylsulfonyl)indolin-5-yl]acrylamide

21. (2e)-3-[1-(benzenesulfonyl)-2,3-dihydro-1h-indol-5-yl]-n-hydroxyprop-2-enamide

2.4 Create Date

2011-10-31

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₆N₂O₄S
Molecular Weight	344.4 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	95.1
Heavy Atom Count	24
Formal Charge	0
Complexity	578
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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Imofinostat

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