Also known as: 1401066-79-2, Bms 906024, Osugacestat, Osugacestat [usan], Al101, Drl23n424r

Molecular Formula

C₂₆H₂₆F₆N₄O₃

Molecular Weight

556.5 g/mol

InChI Key

AYOUDDAETNMCBW-GSHUGGBRSA-N

FDA UNII

DRL23N424R

Osugacestat is a small-molecule gamma secretase (GS) and pan-Notch inhibitor, with potential antineoplastic activity. Upon intravenous administration, osugacestat binds to GS and blocks activation of Notch receptors, which may inhibit the proliferation of tumor cells with an overly-active Notch pathway. 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 that lead to their activation. Overactivation of the Notch signaling pathway, often triggered by activating mutations, has been correlated with increased cellular proliferation and poor prognosis in certain tumor types.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,3R)-N'-[(3S)-1-methyl-2-oxo-5-phenyl-3H-1,4-benzodiazepin-3-yl]-2,3-bis(3,3,3-trifluoropropyl)butanediamide

2.1.2 InChI

InChI=1S/C26H26F6N4O3/c1-36-19-10-6-5-9-18(19)20(15-7-3-2-4-8-15)34-22(24(36)39)35-23(38)17(12-14-26(30,31)32)16(21(33)37)11-13-25(27,28)29/h2-10,16-17,22H,11-14H2,1H3,(H2,33,37)(H,35,38)/t16-,17+,22+/m0/s1

2.1.3 InChI Key

AYOUDDAETNMCBW-GSHUGGBRSA-N

2.1.4 Canonical SMILES

CN1C2=CC=CC=C2C(=NC(C1=O)NC(=O)C(CCC(F)(F)F)C(CCC(F)(F)F)C(=O)N)C3=CC=CC=C3

2.1.5 Isomeric SMILES

CN1C2=CC=CC=C2C(=N[C@@H](C1=O)NC(=O)[C@H](CCC(F)(F)F)[C@H](CCC(F)(F)F)C(=O)N)C3=CC=CC=C3

2.2 Other Identifiers

2.2.1 UNII

DRL23N424R

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 1401066-79-2

2. Bms 906024

3. Osugacestat

4. Osugacestat [usan]

5. Al101

6. Drl23n424r

7. (2r,3s)-n1-((s)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1h-benzo[e][1,4]diazepin-3-yl)-2,3-bis(3,3,3-trifluoropropyl)succinamide

8. Al-101

9. Bm0018

10. Bm-0018

11. (2s,3r)-n'-[(3s)-1-methyl-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl]-2,3-bis(3,3,3-trifluoropropyl)butanediamide

12. Unii-drl23n424r

13. Osugacestat [inn]

14. Chembl4297269

15. Schembl12543868

16. Dtxsid30161234

17. Chebi:131164

18. Mfcd24849414

19. Nsc780812

20. Who 11648

21. Bms 906024 [who-dd]

22. Zinc100285156

23. Db12006

24. Nsc-780812

25. Bb162475

26. Hy-15670

27. Cs-0008191

28. Bms-906024, >=98% (hplc)

29. Q15408421

30. (2r,3s)-n1 -((3s)-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1h-1,4- Benzodiazepin-3-yl)-2,3-bis(3,3,3-trifluoropropyl)butanediamide

31. Butanediamide, N1-((3s)-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1h-1,4-benzodiazepin-3-yl)-2,3-bis(3,3,3-trifluorophenyl)-, (2r,3s)-

32. Butanediamide, N1-((3s)-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1h-1,4-benzodiazepin-3-yl)-2,3-bis(3,3,3-trifluoropropyl)-, (2r,3s)-

2.4 Create Date

2012-10-30

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₆F₆N₄O₃
Molecular Weight	556.5 g/mol
XLogP3	4.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	9
Exact Mass	556.19090968 g/mol
Monoisotopic Mass	556.19090968 g/mol
Topological Polar Surface Area	105 Å²
Heavy Atom Count	39
Formal Charge	0
Complexity	916
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

AL101

AL101

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