Pacritinib

Synopsis, Chemistry

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Also known as: 937272-79-2, Pacritinib (sb1518), Sb1518, Sb-1518, Pacritinib(sb1518), Onx-0803

Molecular Formula

C₂₈H₃₂N₄O₃

Molecular Weight

472.6 g/mol

InChI Key

HWXVIOGONBBTBY-ONEGZZNKSA-N

FDA UNII

G22N65IL3O

Pacritinib is an orally bioavailable inhibitor of Janus kinase 2 (JAK2), the JAK2 mutant JAK2V617F and FMS-like tyrosine kinase 3 (FLT3; CD135; STK1; FLK2), with potential antineoplastic activity. Upon oral administration, pacritinib competes with JAK2 and the JAK2 mutant JAK2V617F for ATP binding, which may result in inhibition of JAK2 activation, inhibition of the JAK-signal transducer and activator of transcription (STAT) signaling pathway, and the induction of apoptosis. In addition, pacritinib targets, binds to and inhibits the activity of FLT3. This inhibits FLT3-mediated signaling and the proliferation of FLT3-expressing cancer cells. JAK2, often upregulated or mutated in a variety of cancer cells, plays a key role in tumor cell proliferation and survival. The JAK2V617F gain-of-function mutation involves a valine-to-phenylalanine modification at position 617. The JAK-STAT signaling pathway is a major mediator of cytokine activity. FLT3, a class III receptor tyrosine kinase (RTK), is overexpressed or mutated in most B-lineage neoplasms and in acute myeloid leukemias. In addition, JAK2 and FLT3 play a key role in the regulation of the inflammatory response and dendritic cell (DC) proliferation, differentiation and function. Inhibition of JAK2- and FLT3-mediated signaling may suppress the generation and differentiation of DCs, and may regulate inflammatory and immune responses.

Pacritinib is a Kinase Inhibitor. The mechanism of action of pacritinib is as a Tyrosine Kinase Inhibitor, and Janus Kinase Inhibitor, and Cytochrome P450 1A2 Inhibitor, and Cytochrome P450 3A4 Inhibitor, and P-Glycoprotein Inhibitor, and Breast Cancer Resistance Protein Inhibitor, and Organic Cation Transporter 1 Inhibitor.

1 2D Structure

Pacritinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(16E)-11-(2-pyrrolidin-1-ylethoxy)-14,19-dioxa-5,7,27-triazatetracyclo[19.3.1.12,6.18,12]heptacosa-1(24),2(27),3,5,8(26),9,11,16,21(25),22-decaene

2.1.2 InChI

InChI=1S/C28H32N4O3/c1-2-13-32(12-1)14-17-35-27-9-8-25-19-24(27)21-34-16-4-3-15-33-20-22-6-5-7-23(18-22)26-10-11-29-28(30-25)31-26/h3-11,18-19H,1-2,12-17,20-21H2,(H,29,30,31)/b4-3+

2.1.3 InChI Key

HWXVIOGONBBTBY-ONEGZZNKSA-N

2.1.4 Canonical SMILES

C1CCN(C1)CCOC2=C3COCC=CCOCC4=CC(=CC=C4)C5=NC(=NC=C5)NC(=C3)C=C2

2.1.5 Isomeric SMILES

C1CCN(C1)CCOC2=C3COC/C=C/COCC4=CC(=CC=C4)C5=NC(=NC=C5)NC(=C3)C=C2

2.2 Other Identifiers

2.2.1 UNII

G22N65IL3O

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 11-(2-pyrrolidin-1-ylethoxy)-14,19-dioxa-5,7,26-triazatetracyclo(19.3.1.1(2,6).1(8,12))heptacosa-1(25),2(26),3,5,8,10,12(27),16,21,23-decaene

2. Sb 1518

3. Sb-1518

4. Sb1518

2.3.2 Depositor-Supplied Synonyms

1. 937272-79-2

2. Pacritinib (sb1518)

3. Sb1518

4. Sb-1518

5. Pacritinib(sb1518)

6. Onx-0803

7. Sb 1518

8. G22n65il3o

9. Vonjo

10. 11-(2-pyrrolidin-1-yl-ethoxy)-14,19-dioxa-5,7,26-triaza-tetracyclo[19.3.1.1(2,6).1(8,12)]heptacosa-1(25),2(26),3,5,8,10,12(27),16,21,23-decaene

11. 14,19-dioxa-5,7,27-triazatetracyclo(19.3.1.12,6.18,12)heptacosa-1(25),2,4,6(27),8,10,12(26),16,21,23-decaene, 11-(2-(1-pyrrolidinyl)ethoxy)-, (16e)-

12. Chembl2181330

13. Pacritinib [inn]

14. Pacritinib (usan/inn)

15. Pacritinib [usan:inn]

16. Pacritinib [usan]

17. Pacritinib [who-dd]

18. Sb-1518 Tfa Salt

19. Unii-g22n65il3o

20. Gtpl7793

21. Schembl1108221

22. Chembl2035187

23. Schembl22819303

24. Ex-a240

25. Dtxsid801045679

26. Amy23364

27. Bax 2201

28. Bcp09091

29. Onx 0803

30. Bdbm50210177

31. Bdbm50400312

32. Mfcd22572772

33. Nsc759674

34. Nsc781626

35. S8057

36. Akos037515687

37. Ccg-269464

38. Cs-1741

39. Db11697

40. Nsc-759674

41. Nsc-781626

42. Ncgc00381564-02

43. Ncgc00390623-02

44. Ac-30280

45. As-35036

46. Hy-16379

47. Sw219864-1

48. D11768

49. Sb1518;sb-1518;sb 1518

50. Q3888693

51. (16e)-11-(2-pyrrolidin-1-ylethoxy)-14,19-dioxa-5,7,27-triazatetracyclo[19.3.1.12,6.18,12]heptacosa-1(24),2(27),3,5,8(26),9,11,16,21(25),22-decaene

2.4 Create Date

2010-07-06

3 Chemical and Physical Properties

Molecular Formula	C₂₈H₃₂N₄O₃
Molecular Weight	472.6 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	472.24744090 g/mol
Monoisotopic Mass	472.24744090 g/mol
Topological Polar Surface Area	68.7 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	644
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1