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Tucatinib

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Chemistry

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Also known as: Irbinitinib, 937263-43-9, Ont-380, Tukysa, 6-diamine, N6-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-n4-(3-methyl-4-((1,2,4)triazolo(1,5-a)pyridin-7-yloxy)phenyl)quinazoline-4,6-diamine

Molecular Formula

C₂₆H₂₄N₈O₂

Molecular Weight

480.5 g/mol

InChI Key

SDEAXTCZPQIFQM-UHFFFAOYSA-N

FDA UNII

234248D0HH

Tucatinib is an orally bioavailable inhibitor of the human epidermal growth factor receptor tyrosine kinase ErbB-2 (also called HER2) with potential antineoplastic activity. Tucatinib selectively binds to and inhibits the phosphorylation of ErbB-2, which may prevent the activation of ErbB-2 signal transduction pathways, resulting in growth inhibition and death of ErbB-2-expressing tumor cells. ErbB-2 is overexpressed in a variety of cancers and plays an important role in cellular proliferation and differentiation.

Tucatinib is a Kinase Inhibitor. The mechanism of action of tucatinib is as a Tyrosine Kinase Inhibitor, and Cytochrome P450 3A Inhibitor, and P-Glycoprotein Inhibitor, and Cytochrome P450 2C8 Inhibitor.

1 2D Structure

Tucatinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

6-N-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-4-N-[3-methyl-4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)phenyl]quinazoline-4,6-diamine

2.1.2 InChI

InChI=1S/C26H24N8O2/c1-16-10-17(5-7-22(16)36-19-8-9-34-23(12-19)28-15-30-34)31-24-20-11-18(4-6-21(20)27-14-29-24)32-25-33-26(2,3)13-35-25/h4-12,14-15H,13H2,1-3H3,(H,32,33)(H,27,29,31)

2.1.3 InChI Key

SDEAXTCZPQIFQM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(C=CC(=C1)NC2=NC=NC3=C2C=C(C=C3)NC4=NC(CO4)(C)C)OC5=CC6=NC=NN6C=C5

2.2 Other Identifiers

2.2.1 UNII

234248D0HH

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Irbinitinib

2. N6-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-n4-(3-methyl-4-((1,2,4)triazolo(1,5-a)pyridin-7-yloxy)phenyl)quinazoline-4,6-diamine

3. N6-(4,5-dihydro-4,4-dmethyl-2-oxazolyl)-n4-(3-methyl-4-((1,2,4)triazolo(1,5-a)pyridin-7-yloxy)phenyl)-4,6-quinazolinediamine

4. Ont-380

5. Tukysa

2.3.2 Depositor-Supplied Synonyms

1. Irbinitinib

2. 937263-43-9

3. Ont-380

4. Tukysa

5. 6-diamine

6. N6-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-n4-(3-methyl-4-((1,2,4)triazolo(1,5-a)pyridin-7-yloxy)phenyl)quinazoline-4,6-diamine

7. 234248d0hh

8. Irbinitinib; Arry-380; Ont-380

9. 4,6-quinazolinediamine, N6-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-n4-(3-methyl-4-((1,2,4)triazolo(1,5-a)pyridin-7-yloxy)phenyl)-

10. N4-(4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)-3-methylphenyl)-n6-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)quinazoline-4,6-diamine

11. N6-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-n4-[3-methyl-4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)phenyl]-4,6-quinazolinediamine

12. Tucatinib [inn]

13. 6-n-(4,4-dimethyl-5h-1,3-oxazol-2-yl)-4-n-[3-methyl-4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)phenyl]quinazoline-4,6-diamine

14. Unii-234248d0hh

15. Ont 380

16. Tukysa (tn)

17. Ont-380;tucatinib

18. Tucatinib [mi]

19. Tucatinib (usan/inn)

20. Tucatinib [usan:inn]

21. Tucatinib [usan]

22. Irbinitinib(arry-380)

23. Irbinitinib; Arry-380

24. Tucatinib [who-dd]

25. Gtpl9922

26. Schembl1193050

27. Tucatinib [orange Book]

28. Chembl3989868

29. Bdbm471617

30. Dtxsid601027958

31. Bcp15983

32. Ex-a1031

33. Mfcd22380467

34. Nsc764581

35. Nsc799335

36. S8362

37. Zinc68250462

38. Arry-380 (ont-380)

39. Akos026750449

40. Ccg-264747

41. Cs-3906

42. Db11652

43. Nsc-764581

44. Nsc-799335

45. Sb17126

46. Us10822334, Compound Ont380

47. Ncgc00482879-02

48. Ac-33037

49. As-56109

50. Bt177688

51. Hy-16069

52. Example 11 [wo2007059257a2]

53. Db-130430

54. A16413

55. D11141

56. A857335

57. Q25100690

58. 4,6-quinazolinediamine,n6-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-n4-[3-methyl-4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)phenyl]-

59. N6-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-n4-[3-methyl-4-([1,2,4]triazolo[1,5-a]pyridin-7-yloxy)phenyl]-4,6-quinazolinediamine;

60. N6-(4,5-dihydro-4,4-dmethyl-2-oxazolyl)-n4-(3-methyl-4-((1,2,4)triazolo(1,5-a)pyridin-7-yloxy)phenyl)-4,6-quinazolinediamine

2.4 Create Date

2011-04-25

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₄N₈O₂
Molecular Weight	480.5 g/mol
XLogP3	4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	6
Exact Mass	480.20222204 g/mol
Monoisotopic Mass	480.20222204 g/mol
Topological Polar Surface Area	111 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	796
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

Tucatinib is indicated with trastuzumab and capecitabine for treatment of adults diagnosed with advanced unresectable or metastatic HER2-positive breast cancer. This includes patients with brain metastases and those who have received one or more prior anti-HER2-based regimens in the metastatic setting.

Tukysa is indicated in combination with trastuzumab and capecitabine for the treatment of adult patients with HER2positive locally advanced or metastatic breast cancer who have received at least 2 prior antiHER2 treatment regimens.

5 Pharmacology and Biochemistry

5.1 Pharmacology

By inhibiting tyrosine kinase, tucatinib exerts anti-tumor activity, reducing the size of HER-2 positive breast cancer tumors. In clinical trials, the regimen of tucatinib and [trastuzumab] showed enhanced activity both in vitro and in vivo when compared to either drug administered by itself.

5.2 MeSH Pharmacological Classification

Antineoplastic Agents

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

TUCATINIB

5.3.2 FDA UNII

234248D0HH

5.3.3 Pharmacological Classes

Cytochrome P450 3A Inhibitors [MoA]; Kinase Inhibitor [EPC]; P-Glycoprotein Inhibitors [MoA]; Tyrosine Kinase Inhibitors [MoA]; Cytochrome P450 2C8 Inhibitors [MoA]

5.4 ATC Code

L01

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01E - Protein kinase inhibitors

L01EH - Human epidermal growth factor receptor 2 (her2) tyrosine kinase inhibitors

L01EH03 - Tucatinib

5.5 Absorption, Distribution and Excretion

Absorption

The Tmax for tucatinib ranges from 1 to 4 hours. One pharmacokinetic study revealed a Cmax of 1120 ng/mL after a dose of 350 mg twice daily with a Tmax ranging from 1 to 3 hours. The AUCtau was reported to be about 7120 hoursng/mL.

Route of Elimination

In a study of radiolabled tucatinib, about 86% of the total dose was excreted in the feces and 4.1% was found in the urine. About 16% of the tucatinib dose recovered in the feces was identified as unchanged tucatinib.

Volume of Distribution

The volume of distribution of tucatinib is about 1670 L. This drug penetrates the blood-brain barrier.

Clearance

The apparent clearance is 148 L/h.

5.6 Metabolism/Metabolites

Tucatinib is metabolized by CYP2C8 with some contributions from CYP3A.

5.7 Biological Half-Life

A pharmacokinetic study revealed a half-life of approximately 5.38 hours. Prescribing information mentions a geometric mean half-life of about 8.21 hours.

5.8 Mechanism of Action

Mutations in the HER-2 gene are observed in some types of breast carcinoma. Tucatinib inhibits the tyrosine kinase enzyme of the HER-2 gene. Mutations of tyrosine kinase in the HER-2 gene lead to cascade effects of increased cell signaling and proliferation, resulting in malignancy. Results of in vitro studies show that tucatinib inhibits the phosphorylation of both HER-2 and HER-3, leading to downstream changes in MAPK and AKT signaling and cell proliferation. Anti-tumor activity occured in the cells that expressed HER-2. In vivo, tucatinib has been shown to inhibit HER-2 expressing tumors, likely by the same mechanism.

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