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Perifosine

Perifosine

Synopsis, Chemistry

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Also known as: 157716-52-4, Krx-0401, 1,1-dimethylpiperidin-1-ium-4-yl octadecyl phosphate, Perifosine (krx-0401), (1,1-dimethylpiperidin-1-ium-4-yl) octadecyl phosphate, Nsc 639966

Molecular Formula

C₂₅H₅₂NO₄P

Molecular Weight

461.7 g/mol

InChI Key

SZFPYBIJACMNJV-UHFFFAOYSA-N

FDA UNII

2GWV496552

Perifosine is a novel alkylphospholipid with antiproliferative properties attributed to protein kinase B inhibition.

1 2D Structure

Perifosine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1,1-dimethylpiperidin-1-ium-4-yl) octadecyl phosphate

2.1.2 InChI

InChI=1S/C25H52NO4P/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-24-29-31(27,28)30-25-20-22-26(2,3)23-21-25/h25H,4-24H2,1-3H3

2.1.3 InChI Key

SZFPYBIJACMNJV-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCCCCCCCCCCCCCCCCOP(=O)([O-])OC1CC[N+](CC1)(C)C

2.2 Other Identifiers

2.2.1 UNII

2GWV496552

2.3 Synonyms

2.3.1 MeSH Synonyms

1. D 21266

2. D-21266

3. Octadecyl-(1,1-dimethyl-4-piperidylio)phosphate

2.3.2 Depositor-Supplied Synonyms

1. 157716-52-4

2. Krx-0401

3. 1,1-dimethylpiperidin-1-ium-4-yl Octadecyl Phosphate

4. Perifosine (krx-0401)

5. (1,1-dimethylpiperidin-1-ium-4-yl) Octadecyl Phosphate

6. Nsc 639966

7. Perifosine [inn]

8. D 21266

9. Nsc-639966

10. 1,1-dimethylpiperidinium-4-yl Octadecyl Phosphate

11. Krx 0401

12. Nsc639966

13. D-21266

14. Chebi:67272

15. 2gwv496552

16. Ncgc00187909-01

17. Piperidinium, 4-[[hydroxy(octadecyloxy)phosphinyl]oxy]-1,1-dimethyl-, Inner Salt

18. 1,1-dimethylpiperidin-1-ium-4-yl Octadecyl Phosphate.

19. Piperidinium, 4-((hydroxy(octadecyloxy)phosphinyl)oxy)-1,1-dimethyl-, Inner Salt

20. Nka17

21. Unii-2gwv496552

22. Octadecyl-(1,1-dimethyl-4-piperidylio)phosphate

23. 4-((hydroxy(octadecyloxy)phosphinyl)oxy)-1,1-dimethylpiperidinium Inner Salt

24. Perifosine [mi]

25. Dsstox_cid_28872

26. Dsstox_rid_83141

27. Perifosine [who-dd]

28. Dsstox_gsid_48946

29. Schembl93872

30. Chembl372764

31. Gtpl7424

32. Dtxsid3048946

33. Bcp00245

34. Ex-a2229

35. Yhi-1003

36. Tox21_113365

37. Bdbm50431630

38. Mfcd00927554

39. Nsc800842

40. S1037

41. Piperidinium,1-dimethyl-, Inner Salt

42. Akos005146344

43. Ccg-269358

44. Cs-0209

45. Db06641

46. Ex-3388

47. Gs-3834

48. Nsc-800842

49. Ncgc00187909-02

50. Ncgc00187909-13

51. Ac-25019

52. Am808092

53. Hy-50909

54. Cas-157716-52-4

55. Ft-0651459

56. P2831

57. A23834

58. D21266

59. Octadecyl-(1,1-dimethyl-4-piperidylio) Phosphate

60. J-500086

61. Q3411917

62. Perifosine; Krx-0401; Nsc 639966; D21266

63. 1,1-dimethylpiperidinium-4-yl Octadecyl Phosphate, Inner Salt

64. 4-hydroxy-1,1-dimethylpiperidinium Hydroxide, Octadecyl Hydrogen Phosphate, Inner Salt

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₅₂NO₄P
Molecular Weight	461.7 g/mol
XLogP3	8.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	20
Exact Mass	461.36339614 g/mol
Monoisotopic Mass	461.36339614 g/mol
Topological Polar Surface Area	58.6 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	454
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

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in solid tumors, multiple myeloma, leukemia (unspecified), lung cancer, and brain cancer.

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

Targeting cellular membranes, perifosine modulates membrane permeability, membrane lipid composition, phospholipid metabolism, and mitogenic signal transduction, resulting in cell differentiation and inhibition of cell growth. This agent also inhibits the anti-apoptotic mitogen-activated protein kinase (MAPK) pathway and modulates the balance between the MAPK and pro-apoptotic stress-activated protein kinase (SAPK/JNK) pathways, thereby inducing apoptosis.