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Zanubrutinib

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Chemistry

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Also known as: 1691249-45-2, Brukinsa, Bgb-3111, Zanubrutinib [inn], Zanubrutinib [usan], Ag9mhg098z

Molecular Formula

C₂₇H₂₉N₅O₃

Molecular Weight

471.5 g/mol

InChI Key

RNOAOAWBMHREKO-QFIPXVFZSA-N

FDA UNII

AG9MHG098Z

Zanubrutinib is an inhibitor of Bruton's tyrosine kinase (BTK) with potential antineoplastic activity. Upon administration, zanubrutinib inhibits the activity of BTK and prevents the activation of the B-cell antigen receptor (BCR) signaling pathway. This prevents both B-cell activation and BTK-mediated activation of downstream survival pathways, which leads to the inhibition of the growth of malignant B-cells that overexpress BTK. BTK, a member of the Src-related BTK/Tec family of cytoplasmic tyrosine kinases, is overexpressed in B-cell malignancies; it plays an important role in B-lymphocyte development, activation, signaling, proliferation and survival.

Zanubrutinib is a Kinase Inhibitor. The mechanism of action of zanubrutinib is as a Bruton's Tyrosine Kinase Inhibitor.

1 2D Structure

Zanubrutinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(7S)-2-(4-phenoxyphenyl)-7-(1-prop-2-enoylpiperidin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

2.1.2 InChI

InChI=1S/C27H29N5O3/c1-2-23(33)31-16-13-18(14-17-31)22-12-15-29-27-24(26(28)34)25(30-32(22)27)19-8-10-21(11-9-19)35-20-6-4-3-5-7-20/h2-11,18,22,29H,1,12-17H2,(H2,28,34)/t22-/m0/s1

2.1.3 InChI Key

RNOAOAWBMHREKO-QFIPXVFZSA-N

2.1.4 Canonical SMILES

C=CC(=O)N1CCC(CC1)C2CCNC3=C(C(=NN23)C4=CC=C(C=C4)OC5=CC=CC=C5)C(=O)N

2.1.5 Isomeric SMILES

C=CC(=O)N1CCC(CC1)[C@@H]2CCNC3=C(C(=NN23)C4=CC=C(C=C4)OC5=CC=CC=C5)C(=O)N

2.2 Other Identifiers

2.2.1 UNII

AG9MHG098Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (7s)-2-(4-phenoxyphenyl)-7-(1-(prop-2-enoyl)piperidin-4-yl)-4,5,6,7-tetrahydropyrazolo(1,5-a)pyrimidine-3-carboxamide

2. 7-(1-acryloyl-4-piperidinyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo(1,5-a)pyrimidine-3-carboxamide

3. Bgb-3111

4. Brukinsa

2.3.2 Depositor-Supplied Synonyms

1. 1691249-45-2

2. Brukinsa

3. Bgb-3111

4. Zanubrutinib [inn]

5. Zanubrutinib [usan]

6. Ag9mhg098z

7. 1691249-45-2 (s-isomer)

8. (7s)-2-(4-phenoxyphenyl)-7-(1-(prop-2-enoyl)piperidin-4-yl)-4,5,6,7-tetrahydropyrazolo(1,5-a)pyrimidine-3-carboxamide

9. Bgb3111

10. (7s)-2-(4-phenoxyphenyl)-7-(1-prop-2-enoylpiperidin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

11. (7s)-4,5,6,7-tetrahydro-7-[1-(1-oxo-2-propen-1-yl)-4-piperidinyl]-2-(4-phenoxyphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

12. (s)-7-(1-acryloylpiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide

13. Pyrazolo(1,5-a)pyrimidine-3-carboxamide, 4,5,6,7-tetrahydro-7-(1-(1-oxo-2-propen-1-yl)-4-piperidinyl)-2-(4-phenoxyphenyl)-, (7s)-

14. Brukinsa (tn)

15. Zanubrutinib [mi]

16. Zanubrutinib (usan/inn)

17. Zanubrutinib [usan:inn]

18. Unii-ag9mhg098z

19. Bgb-3111(zanubrutinib)

20. Zanubrutinib (bgb-3111)

21. Zanubrutinib [who-dd]

22. Gtpl9861

23. Chembl3936761

24. Schembl17842597

25. Bdbm250082

26. Dtxsid701026208

27. Zanubrutinib [orange Book]

28. Compound 27b [us9447106]

29. Bcp29110

30. Ex-a3602

31. Nsc823807

32. S8791

33. Zinc584641430

34. At18252

35. Db15035

36. Hy-101474a

37. Nsc-823807

38. Us9447106, 27b (peak 2)

39. Bs-15529

40. Bz168474

41. Cs-0021869

42. D11422

43. Bgb-3111; Bgb 3111; Bgb3111

44. A934931

45. 1651179-04-2

46. 7-(1-acryloyl-4-piperidinyl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo(1,5-a)pyrimidine-3-carboxamide

2.4 Create Date

2019-01-15

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₂₉N₅O₃
Molecular Weight	471.5 g/mol
XLogP3	3.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Exact Mass	471.22703980 g/mol
Monoisotopic Mass	471.22703980 g/mol
Topological Polar Surface Area	103 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	756
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

4 Drug and Medication Information

4.1 Drug Indication

Zanubrutinib is indicated for the treatment of adult patients with mantle cell lymphoma (MCL) who have received at least one prior therapy. It is used to treat Waldenstrms macroglobulinemia in adults. Zanubrutinib is also indicated for the treatment of relapsed or refractory marginal zone lymphoma (MZL) in adults who have received at least one anti-CD20-based regimen.

Brukinsa as monotherapy is indicated for the treatment of adult patients with Waldenstrms macroglobulinaemia (WM) who have received at least one prior therapy, or in first line treatment for patients unsuitable for chemo-immunotherapy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Zanubrutinib is an immunomodulating agent that decreases the survival of malignant B cells. It inhibits BTK by binding to its active site. It works to inhibit the proliferation and survival of malignant B cells to reduce the tumour size in mantle cell lymphoma.

5.2 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

Hematologic Agents

Drugs that act on blood and blood-forming organs and those that affect the hemostatic system. (See all compounds classified as Hematologic Agents.)

Protein Kinase Inhibitors

Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

ZANUBRUTINIB

5.3.2 FDA UNII

AG9MHG098Z

5.3.3 Pharmacological Classes

Kinase Inhibitor [EPC]; Bruton's Tyrosine Kinase Inhibitors [MoA]

5.4 ATC Code

L01

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01E - Protein kinase inhibitors

L01EL - Bruton's tyrosine kinase (btk) inhibitors

L01EL03 - Zanubrutinib

5.5 Absorption, Distribution and Excretion

Absorption

Following oral administration of zanubrutinib 160 mg twice daily and 320 mg once daily, the mean (%CV) zanubrutinib steady-state concentrations were 2,295 (37%) ngh/mL and 2,180 (41%) ngh/mL, respectively. The mean Cmax (%CV) was 314 (46%) ng/mL following 160 mg twice daily and 543 (51%) ng/mL following 320 mg once daily. The Cmax and AUC of zanubrutinib increase in a dose-proportional manner and there is minimal systemic accumulation after repeated dosing. The median Tmax is 2 hours.

Route of Elimination

Following oral administration of 320 mg radiolabelled zanubrutinib, approximately 87% of the dose was excreted in the feces and about 8% of the dose was recovered in the urine, where less than 1% of the recovered drug comprised of unchanged parent drug.

Volume of Distribution

The geometric mean (%CV) apparent steady-state Vd is 881 (95%) L. The blood-to plasma ratio is about 0.7 to 0.8.

Clearance

The mean (%CV) apparent oral clearance (CL/F) of zanubrutinib is 182 (37%) L/h.

5.6 Metabolism/Metabolites

Zanubrutinib is predominantly metabolized by CYP3A4. Its metabolites have not been characterized.

5.7 Biological Half-Life

Following administration of a single oral dose of 160 mg or 320 mg of zanubrutinib, the mean half-life is approximately 2 to 4 hours.

5.8 Mechanism of Action

Bruton's tyrosine kinase (BTK) is a non-receptor kinase and a signalling molecule for the B cell receptors expressed on the peripheral B cell surface. The BCR signalling pathway plays a crucial role in normal B-cell development but also the proliferation and survival of malignant B cells in many B cell malignancies, including mantle-cell lymphoma (MCL). Once activated by upstream Src-family kinases, BTK phosphorylates phospholipase-C (PLC), leading to Ca2+ mobilization and activation of NF-B and MAP kinase pathways. These downstream cascades promote the expression of genes involved in B cell proliferation and survival. The BCR signalling pathway also induces the anti-apoptotic protein Bcl-xL and regulates the integrin 41 (VLA-4)-mediated adhesion of B cells to vascular cell adhesion molecule-1 (VCAM-1) and fibronectin via BTK. Apart from the direct downstream signal transduction pathway of B cells, BTK is also involved in chemokine receptor, Toll-like receptor (TLR) and Fc receptor signalling pathways. Zanubrutinib inhibits BTK by forming a covalent bond with cysteine 481 residue in the adenosine triphosphate (ATP)binding pocket of BTK, which is the enzyme's active site. This binding specificity is commonly seen with other BTK inhibitors. Due to this binding profile, zanubrutinib may also bind with varying affinities to related and unrelated ATP-binding kinases that possess a cysteine residue at this position. By blocking the BCR signalling pathway, zanubrutinib inhibits the proliferation, trafficking, chemotaxis, and adhesion of malignant B cells, ultimately leading to reduced tumour size. Zanubrutinib was also shown to downregulate programmed death-ligand 1 (PD-1) expression and cytotoxic T lymphocyte-associated antigen-4 (CTLA-4) on CD4+ T cells.

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