Pirtobrutinib

Synopsis, Chemistry

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Also known as: Loxo-305, 2101700-15-4, Pirtobrutinib [usan], Jna39i7zvb, (s)-5-amino-3-(4-((5-fluoro-2-methoxybenzamido)methyl)phenyl)-1-(1,1,1-trifluoropropan-2-yl)-1h-pyrazole-4-carboxamide, Ly3527727

Molecular Formula

C₂₂H₂₁F₄N₅O₃

Molecular Weight

479.4 g/mol

InChI Key

FWZAWAUZXYCBKZ-NSHDSACASA-N

FDA UNII

JNA39I7ZVB

Pirtobrutinib is an orally available, selective, non-covalent Bruton's tyrosine kinase (BTK) inhibitor with potential antineoplastic activity. Upon oral administration, pirtobrutinib selectively and reversibly binds to BTK. This prevents both the activation of the B-cell antigen receptor (BCR) signaling pathway and BTK-mediated activation of downstream survival pathways, thereby inhibiting the growth of malignant B-cells that overexpress BTK. Reversible binding of LOXO-305 may preserve antitumor activity in the presence of certain acquired resistance mutations, including C481 mutated BTK, and limit toxicity associated with inhibition of other non-BTK kinases. 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

Pirtobrutinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-amino-3-[4-[[(5-fluoro-2-methoxybenzoyl)amino]methyl]phenyl]-1-[(2S)-1,1,1-trifluoropropan-2-yl]pyrazole-4-carboxamide

2.1.2 InChI

InChI=1S/C22H21F4N5O3/c1-11(22(24,25)26)31-19(27)17(20(28)32)18(30-31)13-5-3-12(4-6-13)10-29-21(33)15-9-14(23)7-8-16(15)34-2/h3-9,11H,10,27H2,1-2H3,(H2,28,32)(H,29,33)/t11-/m0/s1

2.1.3 InChI Key

FWZAWAUZXYCBKZ-NSHDSACASA-N

2.1.4 Canonical SMILES

CC(C(F)(F)F)N1C(=C(C(=N1)C2=CC=C(C=C2)CNC(=O)C3=C(C=CC(=C3)F)OC)C(=O)N)N

2.1.5 Isomeric SMILES

C[C@@H](C(F)(F)F)N1C(=C(C(=N1)C2=CC=C(C=C2)CNC(=O)C3=C(C=CC(=C3)F)OC)C(=O)N)N

2.2 Other Identifiers

2.2.1 UNII

JNA39I7ZVB

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-amino-3-(4-(((5-fluoro-2-methoxybenzoyl)amino)methyl)phenyl)-1-((2s)-1,1,1-trifluoropropan-2-yl)pyrazole-4-carboxamide

2. Loxo-305

2.3.2 Depositor-Supplied Synonyms

1. Loxo-305

2. 2101700-15-4

3. Pirtobrutinib [usan]

4. Jna39i7zvb

5. (s)-5-amino-3-(4-((5-fluoro-2-methoxybenzamido)methyl)phenyl)-1-(1,1,1-trifluoropropan-2-yl)-1h-pyrazole-4-carboxamide

6. Ly3527727

7. Rxc-005

8. Ly-3527727

9. 1h-pyrazole-4-carboxamide, 5-amino-3-(4-(((5-fluoro-2-methoxybenzoyl)amino)methyl)phenyl)-1-((1s)-2,2,2-trifluoro-1-methylethyl)-

10. 1h-pyrazole-4-carboxamide, 5-amino-3-[4-[[(5-fluoro-2-methoxybenzoyl)amino]methyl]phenyl]-1-[(1s)-2,2,2-trifluoro-1-methylethyl]-

11. Btk Inhibitor 16

12. Unii-jna39i7zvb

13. Pirtobrutinib [inn]

14. Pirtobrutinib [jan]

15. Loxo305

16. Pirtobrutinib (loxo-305)

17. Pirtobrutinib [who-dd]

18. Chembl4650485

19. Schembl19014257

20. Gtpl11628

21. Glxc-25733

22. Ex-a5016

23. Who 11681

24. Bl180882

25. Hy-131328

26. Cs-0133286

27. Loxo-305;ly 3527727; Rxc-005

28. 5-amino-3-(4-((5-fluoro-2-methoxybenzamido)methyl)phenyl)-1-((2s)-1,1,1-trifluoropropan-2-yl)-1h-pyrazole-4-carboxamide

29. 5-amino-3-[4-[[(5-fluoro-2-methoxybenzoyl)amino]methyl]phenyl]-1-[(2s)-1,1,1-trifluoropropan-2-yl]pyrazole-4-carboxamide

2.4 Create Date

2017-08-04

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₁F₄N₅O₃
Molecular Weight	479.4 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	7
Exact Mass	479.15805220 g/mol
Monoisotopic Mass	479.15805220 g/mol
Topological Polar Surface Area	125 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	719
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1