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Also known as: Tvb-2640, 1399177-37-7, Denifanstat [inn], Denifanstat [usan], Fasn-in-2, 4gf95b2lza

Molecular Formula

C₂₇H₂₉N₅O

Molecular Weight

439.6 g/mol

InChI Key

BBGOSBDSLYHMRA-UHFFFAOYSA-N

FDA UNII

4GF95B2LZA

Denifanstat is an orally bioavailable fatty acid synthase (FASN) inhibitor, with potential antineoplastic activity. Upon administration, denifanstat binds to and blocks FASN, which prevents the synthesis of palmitate needed for tumor cell growth and survival. This leads to a reduction in cell signaling, an induction of tumor cell apoptosis and the inhibition of cell proliferation in susceptible tumor cells. FASN, an enzyme responsible for the de novo synthesis of palmitic acid, is overexpressed in tumor cells and plays a key role in tumor metabolism, lipid signaling, tumor cell survival and drug resistance; tumor cells are dependent on increased fatty acid production for their enhanced metabolic needs and rapid growth.

1 2D Structure

Denifanstat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[1-[4-cyclobutyl-2-methyl-5-(5-methyl-1H-1,2,4-triazol-3-yl)benzoyl]piperidin-4-yl]benzonitrile

2.1.2 InChI

InChI=1S/C27H29N5O/c1-17-14-24(22-4-3-5-22)25(26-29-18(2)30-31-26)15-23(17)27(33)32-12-10-21(11-13-32)20-8-6-19(16-28)7-9-20/h6-9,14-15,21-22H,3-5,10-13H2,1-2H3,(H,29,30,31)

2.1.3 InChI Key

BBGOSBDSLYHMRA-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC(=C(C=C1C(=O)N2CCC(CC2)C3=CC=C(C=C3)C#N)C4=NNC(=N4)C)C5CCC5

2.2 Other Identifiers

2.2.1 UNII

4GF95B2LZA

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-(1-(4-cyclobutyl-2-methyl-5-(5-methyl-1h-1,2,4-triazol-3-yl)benzoyl)piperidin-4-yl)benzonitrile

2. Tvb-2640

2.3.2 Depositor-Supplied Synonyms

1. Tvb-2640

2. 1399177-37-7

3. Denifanstat [inn]

4. Denifanstat [usan]

5. Fasn-in-2

6. 4gf95b2lza

7. Tvb 2640 [who-dd]

8. 4-(1-(4-cyclobutyl-2-methyl-5-(3-methyl-1h-1,2,4-triazol-5-yl)benzoyl)piperidin-4-yl)benzonitrile

9. 4-(1-(4-cyclobutyl-2-methyl-5-(5-methyl-4h-1,2,4-triazol-3- Yl)benzoyl)piperidin-4-yl)benzonitrile

10. 4-(1-(4-cyclobutyl-2-methyl-5-(5-methyl-4h-1,2,4-triazol-3-yl)benzoyl)piperidin-4-yl)benzonitrile

11. Us8871790, 480

12. 4-[1-[4-cyclobutyl-2-methyl-5-(5-methyl-1h-1,2,4-triazol-3-yl)benzoyl]piperidin-4-yl]benzonitrile

13. 4-{1-[4-cyclobutyl-2-methyl-5-(5-methyl-1h-1,2,4-triazol-3-yl)benzoyl]piperidin-4-yl}benzonitrile

14. Benzonitrile, 4-(1-(4-cyclobutyl-2-methyl-5-(3-methyl-1h-1,2,4-triazol-5-yl)benzoyl)-4-piperidinyl)-

15. Benzonitrile, 4-[1-[4-cyclobutyl-2-methyl-5-(3-methyl-1h-1,2,4-triazol-5-yl)benzoyl]-4-piperidinyl]-

16. Unii-4gf95b2lza

17. Asc-40

18. Chembl3661754

19. Schembl12488853

20. Bdbm137084

21. Bcp30428

22. Ex-a3643

23. S9714

24. Who 11784

25. Zinc150188638

26. Ac-35714

27. Hy-112829

28. Cs-0066310

29. Tvb2640; Tvb 2640;fasn-in-2

30. A937502

31. Us8871790, 152

2.4 Create Date

2012-10-30

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₂₉N₅O
Molecular Weight	439.6 g/mol
XLogP3	5.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	439.23721057 g/mol
Monoisotopic Mass	439.23721057 g/mol
Topological Polar Surface Area	85.7 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	728
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