ARQ 531

Synopsis, Chemistry

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Also known as: Arq 531, 2095393-15-8, Arq-531, Nemtabrutinib, Jtz51lixn4, Arq531

Molecular Formula

C₂₅H₂₃ClN₄O₄

Molecular Weight

478.9 g/mol

InChI Key

JSFCZQSJQXFJDS-QAPCUYQASA-N

FDA UNII

JTZ51LIXN4

Nemtabrutinib is an orally available reversible inhibitor of Bruton's tyrosine kinase (BTK; Bruton agammaglobulinemia tyrosine kinase), with potential antineoplastic activity. Upon administration, nemtabrutinib non-covalently binds to and inhibits the activity of both the wild-type and the C481S mutated form of BTK, a resistance mutation in the BTK active site in which cysteine is substituted for serine at residue 481. This prevents the activation of the B-cell antigen receptor (BCR) signaling pathway and BTK-mediated activation of downstream survival pathways. This leads to an inhibition of the growth of malignant B-cells that overexpress BTK. Compared to other BTK inhibitors, nemtabrutinib does not require interaction with the BTK C481 site and inhibits the proliferation of cells harboring the BTK C481S mutation. BTK, a member of the Src-related BTK/Tec family of cytoplasmic tyrosine kinases, is overexpressed or mutated in B-cell malignancies; it plays an important role in the development, activation, signaling, proliferation and survival of B-lymphocytes.

1 2D Structure

ARQ 531

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2-chloro-4-phenoxyphenyl)-[4-[[(3R,6S)-6-(hydroxymethyl)oxan-3-yl]amino]-7H-pyrrolo[2,3-d]pyrimidin-5-yl]methanone

2.1.2 InChI

InChI=1S/C25H23ClN4O4/c26-21-10-17(34-16-4-2-1-3-5-16)8-9-19(21)23(32)20-11-27-24-22(20)25(29-14-28-24)30-15-6-7-18(12-31)33-13-15/h1-5,8-11,14-15,18,31H,6-7,12-13H2,(H2,27,28,29,30)/t15-,18+/m1/s1

2.1.3 InChI Key

JSFCZQSJQXFJDS-QAPCUYQASA-N

2.1.4 Canonical SMILES

C1CC(OCC1NC2=NC=NC3=C2C(=CN3)C(=O)C4=C(C=C(C=C4)OC5=CC=CC=C5)Cl)CO

2.1.5 Isomeric SMILES

C1C[C@H](OC[C@@H]1NC2=NC=NC3=C2C(=CN3)C(=O)C4=C(C=C(C=C4)OC5=CC=CC=C5)Cl)CO

2.2 Other Identifiers

2.2.1 UNII

JTZ51LIXN4

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (2-chloro-4-phenoxyphenyl)(4-(((3r,6s)-6-(hydroxymethyl)tetrahydro-2h-pyran-3-yl)amino)-7h-pyrrolo(2,3-d)pyrimidin-5-yl)methanone

2. Arq-531

3. Arq531

2.3.2 Depositor-Supplied Synonyms

1. Arq 531

2. 2095393-15-8

3. Arq-531

4. Nemtabrutinib

5. Jtz51lixn4

6. Arq531

7. Mk1026

8. Mk-1026

9. (2-chloro-4-phenoxyphenyl)-[4-[[(3r,6s)-6-(hydroxymethyl)oxan-3-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone

10. (2-chloro-4-phenoxyphenyl)(4-(((3r,6s)-6-(hydroxymethyl)tetrahydro-2h-pyran-3-yl)amino)-7h-pyrrolo(2,3-d)pyrimidin-5-yl)methanone

11. 1,5-anhydro-2-{[5-(2-chloro-4-phenoxybenzene-1-carbonyl)-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino}-2,3,4-trideoxy-d-erythro-hexitol

12. Arqule 531

13. Unii-jtz51lixn4

14. Nemtabrutinib [inn]

15. Nemtabrutinib [who-dd]

16. Chembl4756476

17. Schembl18756744

18. Schembl18770934

19. Gtpl11413

20. Arq531; Arq 531

21. Bdbm499811

22. Bcp29029

23. Ex-a2727

24. Vid39315

25. Mfcd31692379

26. Nsc830201

27. S8711

28. At10312

29. Ccg-269533

30. Nsc-830201

31. Us11020398, Compound I-123

32. Ac-36883

33. As-79762

34. Hy-112215

35. Cs-0044154

36. (2-chloro-4-phenoxyphenyl)(4-(((3r,6s)-6-(hydroxymethyl)tetrahydro-2h-pyran-3-yl)amino)-3h-pyrrolo[2,3-d]pyrimidin-5-yl)methanone

37. D-erythro-hexitol, 1,5-anhydro-2-((5-(2-chloro-4-phenoxybenzoyl)-7h-pyrrolo(2,3-d)pyrimidin-4-yl)amino)-2,3,4-trideoxy-

38. Hra

2.4 Create Date

2017-08-04

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₂₃ClN₄O₄
Molecular Weight	478.9 g/mol
XLogP3	4.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	7
Exact Mass	478.1407829 g/mol
Monoisotopic Mass	478.1407829 g/mol
Topological Polar Surface Area	109 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	681
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1