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Avapritinib

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Also known as: Blu-285, 1703793-34-3, Ayvakit, Avapritinib [inn], Blu285, (1s)-1-(4-fluorophenyl)-1-[2-[4-[6-(1-methylpyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-yl]piperazin-1-yl]pyrimidin-5-yl]ethanamine

Molecular Formula

C₂₆H₂₇FN₁₀

Molecular Weight

498.6 g/mol

InChI Key

DWYRIWUZIJHQKQ-SANMLTNESA-N

FDA UNII

513P80B4YJ

Avapritinib is an orally bioavailable inhibitor of specific mutated forms of platelet-derived growth factor receptor alpha (PDGFR alpha; PDGFRa) and mast/stem cell factor receptor c-Kit (SCFR), with potential antineoplastic activity. Upon oral administration, avapritinib specifically binds to and inhibits specific mutant forms of PDGFRa and c-Kit, including the PDGFRa D842V mutant and various KIT exon 17 mutants. This results in the inhibition of PDGFRa- and c-Kit-mediated signal transduction pathways and the inhibition of proliferation in tumor cells that express these PDGFRa and c-Kit mutants. PDGFRa and c-Kit, protein tyrosine kinases and tumor-associated antigens (TAAs), are mutated in various tumor cell types; they play key roles in the regulation of cellular proliferation.

Avapritinib is a Kinase Inhibitor. The mechanism of action of avapritinib is as a Tyrosine Kinase Inhibitor, and Cytochrome P450 2C9 Inhibitor, and P-Glycoprotein Inhibitor, and Breast Cancer Resistance Protein Inhibitor, and Multidrug and Toxin Extrusion Transporter 1 Inhibitor, and Multidrug and Toxin Extrusion Transporter 2 K Inhibitor, and Bile Salt Export Pump Inhibitor.

1 2D Structure

Avapritinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1S)-1-(4-fluorophenyl)-1-[2-[4-[6-(1-methylpyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-yl]piperazin-1-yl]pyrimidin-5-yl]ethanamine

2.1.2 InChI

InChI=1S/C26H27FN10/c1-26(28,20-3-5-22(27)6-4-20)21-13-29-25(30-14-21)36-9-7-35(8-10-36)24-23-11-18(16-37(23)33-17-31-24)19-12-32-34(2)15-19/h3-6,11-17H,7-10,28H2,1-2H3/t26-/m0/s1

2.1.3 InChI Key

DWYRIWUZIJHQKQ-SANMLTNESA-N

2.1.4 Canonical SMILES

CC(C1=CC=C(C=C1)F)(C2=CN=C(N=C2)N3CCN(CC3)C4=NC=NN5C4=CC(=C5)C6=CN(N=C6)C)N

2.1.5 Isomeric SMILES

C[C@](C1=CC=C(C=C1)F)(C2=CN=C(N=C2)N3CCN(CC3)C4=NC=NN5C4=CC(=C5)C6=CN(N=C6)C)N

2.2 Other Identifiers

2.2.1 UNII

513P80B4YJ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (1s)-1-(4-fluorophenyl)-1-(2-(4-(6-(1-methyl-1h-pyrazol-4-yl)pyrrolo(2,1-f)(1,2,4)triazin-4-yl)-1-piperazinyl)-5-pyrimidinyl)ethanamine

2. 5-pyrimidinemethanamine, Alpha-(4-fluorophenyl)-alpha-methyl-2-(4-(6-(1-methyl-1h-pyrazol-4-yl)pyrrolo(2,1-f)(1,2,4)triazin-4-yl)-1-piperazinyl)-, (alphas)-

3. Ayvakit

4. Blu-285

2.3.2 Depositor-Supplied Synonyms

1. Blu-285

2. 1703793-34-3

3. Ayvakit

4. Avapritinib [inn]

5. Blu285

6. (1s)-1-(4-fluorophenyl)-1-[2-[4-[6-(1-methylpyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-yl]piperazin-1-yl]pyrimidin-5-yl]ethanamine

7. 513p80b4yj

8. C-366

9. 70c366

10. X720776

11. X-720776

12. Ayvakyt

13. Mfcd31544325

14. Ayvakit (tn)

15. Avapritinib [mi]

16. Avapritinib (usan/inn)

17. Avapritinib [usan]

18. Avapritinib (blu-285)

19. Blu-285 (avapritinib)

20. Avapritinib [who-dd]

21. Unii-513p80b4yj

22. Chembl4204794

23. Schembl16652297

24. Gtpl10368

25. Avapritinib [orange Book]

26. Blu 285

27. Bdbm469269

28. Dtxsid301027935

29. Amy16753

30. Ex-a1366

31. Us10807985, Compound 44

32. Nsc801082

33. S8553

34. Akos037648993

35. Ccg-269677

36. Cs-7577

37. Db15233

38. Nsc-801082

39. (s)-1-(4-fluorophenyl)-1-(2-(4-(6-(1-methyl-1h-pyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-yl)piperazin-1-yl)pyrimidin-5-yl)ethan-1-amine

40. Ac-31598

41. Bb166456

42. Bs-16206

43. Hy-101561

44. D11279

45. Q29213676

46. (1s)-1-(4-fluorophenyl)-1-(2-(4-(6-(1-methyl-1h-pyrazol-4-yl)pyrrolo(2,1-f)(1,2,4)triazin-4-yl)-1-piperazinyl)-5-pyrimidinyl)ethanamine

47. (1s)-1-(4-fluorophenyl)-1-(2-(4-(6-(1-methyl-1h-pyrazol-4-yl)pyrrolo(2,1-f)(1,2,4)triazin-4-yl)piperazin-1-yl)pyrimidin-5-yl)ethan-1-amine

48. (s)-1-(4-fluorophenyl)-1-(2-(4-(6-(1-methyl-1h-pyrazol-4-yl)pyrrolo(2,1-f)(1,2,4)triazin-4-yl)piperazin-yl)pyrimidin-5-yl)ethan-1-amine

49. (s)-1-(4-fluorophenyl)-1-(2-(4-(6-(1-methyl-1h-pyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-yl)piperazin-1-yl)pyrimidin-5-yl)ethanamine

50. 5-pyrimidinemethanamine, .alpha.-(4-fluorophenyl)-.alpha.-methyl-2-(4-(6-(1-methyl-1h-pyrazol-4-yl)pyrrolo(2,1-f)(1,2,4)triazin-4-yl)-1-piperazinyl)-, (.alpha.s)-

2.4 Create Date

2016-02-23

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₇FN₁₀
Molecular Weight	498.6 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	5
Exact Mass	498.24041907 g/mol
Monoisotopic Mass	498.24041907 g/mol
Topological Polar Surface Area	106 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	752
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

Avapritinib is indicated for the treatment of unresectable, metastatic gastrointestinal stromal tumors with a platelet-derived growth factor receptor alpha exon 18 mutation.

Treatment of mastocytosis

Treatment of all conditions included in the category of malignant neoplasms (except haematopoietic and lymphoid tissue neoplasms)

Ayvakyt is indicated as monotherapy for the treatment of adult patients with unresectable or metastatic gastrointestinal stromal tumours (GIST) harbouring the platelet-derived growth factor receptor alpha (PDGFRA) D842V mutation.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Avapritinib is a selective kinase inhibitor that negatively modulates the action of cell transporters to resensitize them to other chemotherapies. It has a long duration of action as it is given once daily. Patients should be counselled regarding the risk of intracranial hemorrhage, CNS effects, and embryo-fetal toxicity.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

AVAPRITINIB

5.2.2 FDA UNII

513P80B4YJ

5.2.3 Pharmacological Classes

Breast Cancer Resistance Protein Inhibitors [MoA]; Cytochrome P450 2C9 Inhibitors [MoA]; Kinase Inhibitor [EPC]; Multidrug and Toxin Extrusion Transporter 1 Inhibitors [MoA]; Multidrug and Toxin Extrusion Transporter 2 K Inhibitors [MoA]; P-Glycoprotein Inhibitors [MoA]; Tyrosine Kinase Inhibitors [MoA]; Bile Salt Export Pump Inhibitors [MoA]

5.3 ATC Code

L01EX18

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01E - Protein kinase inhibitors

L01EX - Other protein kinase inhibitors

L01EX18 - Avapritinib

5.4 Absorption, Distribution and Excretion

Absorption

A 300mg oral dose of avapritinib reaches a C_max of 813ng/mL with a T_max of 2.0-4.1h and an AUC of 15400h\*ng/mL.

Route of Elimination

Avapritinib is 70% eliminated in the feces with 11% as the unchanged drug and 18% eliminated in the urine with 0.23% as the unchanged drug.

Volume of Distribution

The mean apparent volume of distribution is 1200L.

Clearance

The mean apparent oral clearance of avapritinib is 19.5L/h.

5.5 Metabolism/Metabolites

Avapritinib is metabolized mainly by CYP3A4 and CYP2C9 in vitro. A 310mg oral dose is recovered as 49% unchanged drug, 35% hydroxy glucuronide metabolite, and 14% oxidatively deaminated metabolite.

5.6 Biological Half-Life

The half life of avapritinib is 32-57h.

5.7 Mechanism of Action

Avapritinib has a negative modulating effect on the transporters ABCB1 and ABCG2, which mediate the multidrug resistance phenotype of some cancers. This modulation may be due to interactions of avapritinib with the drug binding pocket of these transporters. Negative modulation of these transporters, resensitizes cancerous cells to treatment with chemotherapeutic agents like [paclitaxel].

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