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    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
    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 Weight 472.6 g/mol
    Molecular Formula C28H32N4O3
    XLogP33.8
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count4
    Exact Mass472.24744090 g/mol
    Monoisotopic Mass472.24744090 g/mol
    Topological Polar Surface Area68.7 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity644
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Treatment of post-essential thrombocythaemia myelofibrosis, Treatment of post-polycythaemia vera myelofibrosis

    5 Pharmacology and Biochemistry
    5.1 FDA Pharmacological Classification
    5.1.1 Active Moiety
    PACRITINIB
    5.1.2 FDA UNII
    G22N65IL3O
    5.1.3 Pharmacological Classes
    Mechanisms of Action [MoA] - Organic Cation Transporter 1 Inhibitors
    5.2 ATC Code

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01E - Protein kinase inhibitors

    L01EJ - Janus-associated kinase (jak) inhibitors

    L01EJ03 - Pacritinib

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