Also known as: Apr-246, 5291-32-7, Eprenetapopt, 2-(hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one, Apr 246, 2-(hydroxymethyl)-2-(methoxymethyl)quinuclidin-3-one

Molecular Formula

C₁₀H₁₇NO₃

Molecular Weight

199.25 g/mol

InChI Key

BGBNULCRKBVAKL-UHFFFAOYSA-N

FDA UNII

Z41TGB4080

Eprenetapopt is a methylated derivative and structural analog of PRIMA-1 (p53 re-activation and induction of massive apoptosis), with potential antineoplastic activity. Upon administration, eprenetapopt covalently modifies the core domain of mutated forms of cellular tumor antigen p53 (p53) through the alkylation of thiol groups. These modifications restore both the wild-type conformation and function to mutant p53, which reconstitutes endogenous p53 activity, leading to cell cycle arrest and apoptosis in tumor cells. This agent may work synergistically with other antineoplastic agents. p53, a tumor suppressor and transcription factor normally activated upon DNA damage, is frequently mutated and overexpressed in cancer cells; it plays a key role in both DNA repair and the induction of apoptosis.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one

2.1.2 InChI

InChI=1S/C10H17NO3/c1-14-7-10(6-12)9(13)8-2-4-11(10)5-3-8/h8,12H,2-7H2,1H3

2.1.3 InChI Key

BGBNULCRKBVAKL-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COCC1(C(=O)C2CCN1CC2)CO

2.2 Other Identifiers

2.2.1 UNII

Z41TGB4080

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-hydroxymethyl-2-methoxymethylazabicyclo(2.2.2)octan-3-one

2. Apr-246

3. Eprenetapopt

4. Prima-1(met)

2.3.2 Depositor-Supplied Synonyms

1. Apr-246

2. 5291-32-7

3. Eprenetapopt

4. 2-(hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one

5. Apr 246

6. 2-(hydroxymethyl)-2-(methoxymethyl)quinuclidin-3-one

7. Eprenetapopt [usan]

8. Z41tgb4080

9. 3-quinuclidinone, 2-(hydroxymethyl)-2-(methoxymethyl)-

10. 1-azabicyclo(2.2.2)octan-3-one, 2-(hydroxymethyl)-2-(methoxymethyl)-

11. Prima 1met

12. Unii-z41tgb4080

13. Eprenetapopt [inn]

14. Mls006010767

15. Eprenetapopt [who-dd]

16. Apr246

17. Schembl2228161

18. Chembl3186011

19. Schembl21636035

20. Prima-1met(apr-246)

21. Apr-246 (prima-1met)

22. Dtxsid401164013

23. Bcp20294

24. Ex-a2772

25. Mfcd20620963

26. Nsc791496

27. S7724

28. Who 11387

29. Akos024457764

30. Ccg-266578

31. Cs-7614

32. Db11684

33. Nsc-791496

34. Sb19737

35. Ncgc00346881-01

36. Ac-32964

37. As-72033

38. Ba176962

39. Hy-19980

40. Smr004701457

41. A901731

42. Q27294965

43. 2-hydroxymethyl-2-methoxymethyl-1-azabicyclo[2.2.2]octan-3-one

2.4 Create Date

2011-06-02

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₇NO₃
Molecular Weight	199.25 g/mol
XLogP3	-0.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	199.12084340 g/mol
Monoisotopic Mass	199.12084340 g/mol
Topological Polar Surface Area	49.8 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	236
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

APR 246

APR 246

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