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Also known as: Mrtx1719, 2630904-44-6, Benzonitrile, 2-(4-(4-(aminomethyl)-1,2-dihydro-1-oxo-6-phthalazinyl)-1-methyl-1h-pyrazol-5-yl)-4-chloro-6-(cyclopropyloxy)-3-fluoro-, (2s)-, (m)-27, 2-[4-[4-(aminomethyl)-1-oxo-2h-phthalazin-6-yl]-2-methylpyrazol-3-yl]-4-chloro-6-cyclopropyloxy-3-fluorobenzonitrile, 2-(4-(4-(aminomethyl)-1-oxo-2h-phthalazin-6-yl)-2-methylpyrazol-3-yl)-4-chloro-6-cyclopropyloxy-3-fluorobenzonitrile

Molecular Formula

C₂₃H₁₈ClFN₆O₂

Molecular Weight

464.9 g/mol

InChI Key

BZKIOORWZAXIBA-UHFFFAOYSA-N

FDA UNII

UHN5PKM648

PRMT5 Inhibitor BMS-986504 is an orally bioavailable methylthioadenosine (MTA)-selective inhibitor of the protein arginine methyltransferase 5 (PRMT5), with potential antineoplastic activity. Upon oral administration, PRMT5 inhibitor BMS-986504 targets, binds to and inhibits PRMT5 that is bound to MTA, a complex that is elevated in methylthioadenosine phosphorylase (MTAP)-deleted cancer cells, thereby specifically inhibiting the function of PRMT5 solely within MTAP-deleted cancer cells and not in normal, healthy cells. By inhibiting the methyltransferase activity of PRMT5, levels of both monomethylated and dimethylated arginine residues in histones H2A, H3 and H4 are decreased. This modulates the expression of genes involved in several cellular processes, including cellular proliferation. This may increase the expression of antiproliferative genes and/or decrease the expression of genes that promote cell proliferation, which may lead to decreased growth of rapidly proliferating cancer cells. BMS-986504 also causes dysregulated RNA splicing and decreased retinoblastoma protein (pRb). Together, this decreases proliferation and increases apoptosis specifically in MTAP-deleted cancer cells. PRMT5, a type II methyltransferase that catalyzes the formation of both omega-N monomethylarginine (MMA) and symmetric dimethylarginine (sDMA) on histones and a variety of other protein substrates involved in signal transduction and cellular transcription, is essential for the viability of cancer and normal cells. It is overexpressed in several neoplasms. Elevated levels are associated with decreased patient survival. MTAP is deleted in certain cancer cells leading to an accumulation of the metabolite MTA; MTA binds to and partially inhibits the activity of PRMT5.

1 2D Structure

Mrtx-1719

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[4-[4-(aminomethyl)-1-oxo-2H-phthalazin-6-yl]-1-methylpyrazol-5-yl]-4-chloro-6-cyclopropyloxy-3-fluorobenzonitrile

2.1.2 InChI

InChI=1S/C23H18ClFN6O2/c1-31-22(20-15(8-26)19(33-12-3-4-12)7-17(24)21(20)25)16(10-28-31)11-2-5-13-14(6-11)18(9-27)29-30-23(13)32/h2,5-7,10,12H,3-4,9,27H2,1H3,(H,30,32)

2.1.3 InChI Key

BZKIOORWZAXIBA-UHFFFAOYSA-N

2.2 Other Identifiers

2.2.1 UNII

UHN5PKM648

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Mrtx1719

2. 2630904-44-6

3. Benzonitrile, 2-(4-(4-(aminomethyl)-1,2-dihydro-1-oxo-6-phthalazinyl)-1-methyl-1h-pyrazol-5-yl)-4-chloro-6-(cyclopropyloxy)-3-fluoro-, (2s)-

4. (m)-27

5. 2-[4-[4-(aminomethyl)-1-oxo-2h-phthalazin-6-yl]-2-methylpyrazol-3-yl]-4-chloro-6-cyclopropyloxy-3-fluorobenzonitrile

6. 2-(4-(4-(aminomethyl)-1-oxo-2h-phthalazin-6-yl)-2-methylpyrazol-3-yl)-4-chloro-6-cyclopropyloxy-3-fluorobenzonitrile

7. Refchem:201848

8. Mrtx 1719

9. Prmt5-mta Inhibitor Mrtx1719

10. Prmt5-mta Complex Inhibitor Mrtx1719

11. Mta-cooperative Prmt5 Inhibitor Mrtx1719

12. 2630904-45-7

13. (s)-mrtx-1719

14. Navlimetostat

15. Ay4a8wd6js

16. Unii-ay4a8wd6js

17. (2r)-2-(4-(4-(aminomethyl)-1-oxo-1,2-dihydrophthalazin-6-yl)-1-methyl-1h-pyrazol-5-yl)-4-chloro-6-cyclopropoxy-3-fluorobenzonitrile

18. 2-(4-(4-(aminomethyl)-1-oxo-1,2-dihydrophthalazin-6-yl)-1-methyl-1h-pyrazol-5-yl)-4-chloro-6-cyclopropoxy-3-fluorobenzonitrile

19. 2629314-96-9

20. Benzonitrile, 2-(4-(4-(aminomethyl)-1,2-dihydro-1-oxo-6-phthalazinyl)-1-methyl-1h-pyrazol-5-yl)-4-chloro-6-(cyclopropyloxy)-3-fluoro-, (2r)-

21. Benzonitrile, 2-[4-[4-(aminomethyl)-1,2-dihydro-1-oxo-6-phthalazinyl]-1-methyl-1h-pyrazol-5-yl]-4-chloro-6-(cyclopropyloxy)-3-fluoro-, (2r)-

22. Navlimetostat [inn]

23. Mrtx1719 Racemate

24. Mrtx1719 Hcl

25. Uhn5pkm648

26. C23h18clfn6o2

27. Mrtx-1719 Hcl

28. Orb1303284

29. Chembl5075255

30. Schembl23087302

31. Schembl29735316

32. Ex-a5505a

33. Ex-a5505b

34. Gtpl12116

35. Wlz3536

36. Glxc-25300

37. Mrtx-1719?

38. Ex-a5505

39. Mfcd34604075

40. Nsc840578

41. Nsc841295

42. Akos040757913

43. Hy-139611b

44. Nsc-840578

45. Nsc-841295

46. Ac-36984

47. Da-69270

48. Da-75760

49. Ms-28566

50. Sy310874

51. Hy-139611

52. Cs-0226219

53. Cs-0343422

54. F78345

55. (2m)-2-(4-(4-(aminomethyl)-1-oxo-1,2-dihydrophthalazin-6-yl)-1-methyl-1h-pyrazol-5-yl)-4-chloro-6-cyclopropoxy-3-fluorobenzonitrile

56. 2-[4-[4-(aminomethyl)-1-oxo-1,2-dihydrophthalazin-6-yl]-1-methyl-5-pyrazolyl]-4-chloro-6-cyclopropoxy-3-fluorobenzonitrile

57. 2-[4-[4-(aminomethyl)-1-oxo-2h-phthalazin-6-yl]-2-methyl-pyrazol-3-yl]-4-chloro-6-(cyclopropoxy)-3-fluoro-benzonitrile

58. Benzonitrile, 2-[4-[4-(aminomethyl)-1,2-dihydro-1-oxo-6-phthalazinyl]-1-methyl-1h-pyrazol-5-yl]-4-chloro-6-(cyclopropyloxy)-3-fluoro-

2.4 Create Date

2021-08-21

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₁₈ClFN₆O₂
Molecular Weight	464.9 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	5
Exact Mass	Da
Monoisotopic Mass	Da
Topological Polar Surface Area	118
Heavy Atom Count	33
Formal Charge	0
Complexity	846
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

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