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Chemistry

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Also known as: Pf-03084014, 1290543-63-3, Pf-3084014, 865773-15-5, Pf 3084014, Nirogacestat [usan]
Molecular Formula
C27H41F2N5O
Molecular Weight
489.6  g/mol
InChI Key
VFCRKLWBYMDAED-REWPJTCUSA-N
FDA UNII
QZ62892OFJ

Nirogacestat Hydrobromide
Nirogacestat is a selective gamma secretase (GS) inhibitor with potential antitumor activity. Nirogacestat binds to GS, blocking proteolytic activation of Notch receptors; Notch signaling pathway inhibition may follow, which may result in the induction of apoptosis in tumor cells that overexpress Notch. The integral membrane protein GS is a multi-subunit protease complex that cleaves single-pass transmembrane proteins, such as Notch receptors, at residues within their transmembrane domains. Overexpression of the Notch signaling pathway has been correlated with increased tumor cell growth and survival.
1 2D Structure

Nirogacestat Hydrobromide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2-[[(2S)-6,8-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl]amino]-N-[1-[1-(2,2-dimethylpropylamino)-2-methylpropan-2-yl]imidazol-4-yl]pentanamide
2.1.2 InChI
InChI=1S/C27H41F2N5O/c1-7-8-23(32-20-10-9-18-11-19(28)12-22(29)21(18)13-20)25(35)33-24-14-34(17-31-24)27(5,6)16-30-15-26(2,3)4/h11-12,14,17,20,23,30,32H,7-10,13,15-16H2,1-6H3,(H,33,35)/t20-,23-/m0/s1
2.1.3 InChI Key
VFCRKLWBYMDAED-REWPJTCUSA-N
2.1.4 Canonical SMILES
CCCC(C(=O)NC1=CN(C=N1)C(C)(C)CNCC(C)(C)C)NC2CCC3=C(C2)C(=CC(=C3)F)F
2.1.5 Isomeric SMILES
CCC[C@@H](C(=O)NC1=CN(C=N1)C(C)(C)CNCC(C)(C)C)N[C@H]2CCC3=C(C2)C(=CC(=C3)F)F
2.2 Other Identifiers
2.2.1 UNII
QZ62892OFJ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-3-ylamino)-n-(1-(2-methyl-1-(neopentylamino)propan-2-yl)-1h-imidazol-4-yl)pentanamide

2. Pf 03084014

3. Pf 3084014

4. Pf-03084014

5. Pf-3084014

6. Pf03084014

7. Pf3084014

2.3.2 Depositor-Supplied Synonyms

1. Pf-03084014

2. 1290543-63-3

3. Pf-3084014

4. 865773-15-5

5. Pf 3084014

6. Nirogacestat [usan]

7. Pf 03084014

8. Pf3084014

9. Qz62892ofj

10. (s)-2-(((s)-6,8-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)amino)-n-(1-(2-methyl-1-(neopentylamino)propan-2-yl)-1h-imidazol-4-yl)pentanamide

11. (2s)-2-[[(2s)-6,8-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl]amino]-n-[1-[1-(2,2-dimethylpropylamino)-2-methylpropan-2-yl]imidazol-4-yl]pentanamide

12. Pf-03084014 (pf-3084014)

13. (s)-2-((s)-6,8-difluoro-1,2,3,4-tetrahydronaphthalen-2-ylamino)-n-(1-(2-methyl-1-(neopentylamino)propan-2-yl)-1h-imidazol-4-yl)pentanamide

14. Unii-qz62892ofj

15. Nirogacestat (usan/inn)

16. Nirogacestat [inn]

17. Z-3181

18. Nirogacestat [who-dd]

19. Gtpl7746

20. Chembl1770916

21. Schembl13184754

22. Dtxsid60235679

23. Ex-a855

24. Pf-3084014 (y-secratase)

25. Hms3886p21

26. Bdbm50458159

27. Mfcd19980705

28. Nsc754348

29. S8018

30. Zinc38217837

31. Akos030526383

32. Ccg-269609

33. Cs-1689

34. Db12005

35. Nsc-754348

36. Ncgc00378713-01

37. 2-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-3-ylamino)-n-(1-(2-methyl-1-(neopentylamino)propan-2-yl)-1h-imidazol-4-yl)pentanamide

38. Ac-36191

39. As-56178

40. Hy-15185

41. Pf-03084014-pf-3084014

42. A11993

43. D10960

44. F17429

45. A910640

46. Nirogacestat (pf-03084014, Pf-3084014)

47. Q27088329

48. Pf-03084014;pf-3084014;865773-15-5;

49. (2s)-2-(((2s)-6,8-difluoro-1,2,3,4-tetrahydro-2-naphthalenyl)amino)-n-(1-(2-((2,2-dimethylpropyl)amino)-1,1-dimethylethyl)-1h-imidazol-4-yl)pentanamide

50. (2s)-2-{[(2s)-6,8-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl]amino}-n-(1-{1-[(2,2-dimethylpropyl)amino]-2-methylpropan-2-yl}-1h-imidazol-4-yl)pentanamide

51. Pentanamide, 2-(((2s)-6,8-difluoro-1,2,3,4-tetrahydro-2-naphthalenyl)amino)-n-(1-(2-((2,2-dimethylpropyl)amino)-1,1-dimethylethyl)-1h-imidazol-4-yl)-, (2s)-

52. Pentanamide, 2-((6,8-difluoro-1,2,3,4-tetrahydro-2-naphthalenyl)amino)-n-(1-(2-((2,2-dimethylpropyl)amino)-1,1-dimethylethyl)-1h-imidazol-4-yl)-, (2s)-

53. Pentanamide, 2-[(6,8-difluoro-1,2,3,4-tetrahydro-2-naphthalenyl)amino]-n-[1-[2-[(2,2-dimethylpropyl)amino]-1,1-dimethylethyl]-1h-imidazol-4-yl]-, (2s)

2.4 Create Date
2010-07-06
3 Chemical and Physical Properties
Molecular Weight 489.6 g/mol
Molecular Formula C27H41F2N5O
XLogP34.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count11
Exact Mass489.32791727 g/mol
Monoisotopic Mass489.32791727 g/mol
Topological Polar Surface Area71 Ų
Heavy Atom Count35
Formal Charge0
Complexity685
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Gamma Secretase Inhibitors and Modulators

Agents that suppress GAMMA-SECRETASE by inhibiting or modulating its activities. Targeted enzymatic activities include its involvement in accumulation of toxic AMYLOID BETA-PEPTIDES (e.g., Aβ42) in ALZHEIMER DISEASE and activation of NOTCH RECEPTOR mediated SIGNAL PATHWAYS in certain cancer types. (See all compounds classified as Gamma Secretase Inhibitors and Modulators.)


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