Please Wait
Applying Filters...
menu
    • menu
    DRL offers a portfolio of products & services, including APIs, CMO services, generics, biosimilars & differentiated formulations.

    Virtual Booth

    Contact Supplier

    Valsynthese, part of the SSE Group, is a CDMO focused on highly energetic and highly hazardous chemistry.

    Virtual Booth

    Contact Supplier

    xyz-pharma-m-2024-10-07

    Virtual Booth

    Contact Supplier

    With Fermion, start the journey of your innovative API.

    Virtual Booth

    Contact Supplier

    Bloomage is a one-stop source for CEP Sodium Hyaluronate and Hyaluronic Acid// FDA-inspected & GMP-certified.

    Virtual Booth

    Contact Supplier

    xyz-pharma-m-2024-10-07

    Virtual Booth

    Contact Supplier

    Menu

    Itacitinib

    DEVELOPMENTS

    INTERMEDIATES

    DIGITAL CONTENT

    PharmaCompass
    Xls

    Filters

    clear-filterReset all filters
    2D Structure
    Also known as: 1334298-90-6, Incb039110, Incb-039110, 2-(3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-1-(1-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-yl)azetidin-3-yl)acetonitrile, Incb39110, 19j3781lpm
    Molecular Formula
    C26H23F4N9O
    Molecular Weight
    553.5  g/mol
    InChI Key
    KTBSXLIQKWEBRB-UHFFFAOYSA-N
    FDA UNII
    19J3781LPM
    Itacitinib is an orally bioavailable inhibitor of Janus-associated kinase 1 (JAK1) with potential antineoplastic and immunomodulating activities. Upon oral administration, itacitinib selectively inhibits JAK-1, thereby inhibiting the phosphorylation of signal transducer and activator of transcription (STAT) proteins and the production of proinflammatory factors induced by other cytokines, including interleukin-23 (IL-23) and interleukin-6 (IL-6). The JAK-STAT pathway plays a key role in the signaling of many cytokines and growth factors and is involved in cellular proliferation, growth, hematopoiesis, and the immune response; JAK kinases may be upregulated in inflammatory diseases, myeloproliferative disorders, and various malignancies.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[1-[1-[3-fluoro-2-(trifluoromethyl)pyridine-4-carbonyl]piperidin-4-yl]-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]acetonitrile
    2.1.2 InChI
    InChI=1S/C26H23F4N9O/c27-20-18(1-7-32-22(20)26(28,29)30)24(40)37-9-3-17(4-10-37)38-13-25(14-38,5-6-31)39-12-16(11-36-39)21-19-2-8-33-23(19)35-15-34-21/h1-2,7-8,11-12,15,17H,3-5,9-10,13-14H2,(H,33,34,35)
    2.1.3 InChI Key
    KTBSXLIQKWEBRB-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CN(CCC1N2CC(C2)(CC#N)N3C=C(C=N3)C4=C5C=CNC5=NC=N4)C(=O)C6=C(C(=NC=C6)C(F)(F)F)F
    2.2 Other Identifiers
    2.2.1 UNII
    19J3781LPM
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (1-(1-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)-4-piperidinyl)-3-(4-(1h-pyrrolo(2,3-d)pyrimidin-4-yl)-1h-pyrazol-1-yl)-3-azetidinyl)acetonitrile

    2.3.2 Depositor-Supplied Synonyms

    1. 1334298-90-6

    2. Incb039110

    3. Incb-039110

    4. 2-(3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-1-(1-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-yl)azetidin-3-yl)acetonitrile

    5. Incb39110

    6. 19j3781lpm

    7. 2-[1-[1-[3-fluoro-2-(trifluoromethyl)pyridine-4-carbonyl]piperidin-4-yl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]azetidin-3-yl]acetonitrile

    8. 3-azetidineacetonitrile, 1-(1-((3-fluoro-2-(trifluoromethyl)-4-pyridinyl)carbonyl)-4-piperidinyl)-3-(4-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)-1h-pyrazol-1-yl)-

    9. 1-[1-[[3-fluoro-2-(trifluoromethyl)-4-pyridinyl]carbonyl]-4-piperidinyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]-3-azetidineacetonitrile

    10. Itacitinib [usan]

    11. Unii-19j3781lpm

    12. 2-(3-(4-(7h-pyrrolo(2,3-d)pyrimidin-4-yl)-1h-pyrazol-1-yl)-1-(1-(3-fluoro-2-(trifluoromethyl)isonicotinoyl)piperidin-4-yl)azetidin-3-yl)acetonitrile

    13. Examlpe 294 [wo2011112662]

    14. Itacitinib [inn]

    15. Itacitinib (usan/inn)

    16. Itacitinib [usan:inn]

    17. Itacitinib [who-dd]

    18. Itacitinib (incb39110)

    19. Itacitinib(incb039110)

    20. Itacitinib; Incb039110

    21. Gtpl8364

    22. Schembl2396080

    23. Chembl3622820

    24. C26h23f4n9o

    25. Amy1814

    26. Bdbm246868

    27. Incb 39110

    28. Incb-39110

    29. Bcp13794

    30. Ex-a1674

    31. Nsc792849

    32. Nsc796224

    33. Nsc801001

    34. S7812

    35. Zinc118795962

    36. At16231

    37. Ccg-270017

    38. Cs-5593

    39. Db12154

    40. Nsc-792849

    41. Nsc-796224

    42. Nsc-801001

    43. Sb13363

    44. {1-{1-[3-fluoro-2-(trifluoromethyl)isonicotinoyl]piperidin-4-yl}-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]azetidin-3-yl}acetonitrile

    45. 1651228-00-0

    46. 2-(1-{1-[3-fluoro-2-(trifluoromethyl)pyridine-4-carbonyl]piperidin-4-yl}-3-(4-{7h-pyrrolo[2,3-d]pyrimidin-4-yl}-1h-pyrazol-1-yl)azetidin-3-yl)acetonitrile

    47. Ac-29031

    48. As-75259

    49. Hy-16997

    50. A14390

    51. D10944

    52. Us10053465, 7

    53. A902364

    54. Q27891174

    55. Incb039110;incb-039110;incb 039110

    56. Incb39110;incb-39110;incb 39110; Incb039110; Incb-039110; Incb 039110

    57. (1-(1-(3-fluoro-2-(trifluoromethyl)pyridine- 4-carbonyl)piperidin-4-yl)-3-(4-(7h-pyrrolo(2,3-d)pyrimidin- 4-yl)-1h-pyrazol-1-yl)azetidin-3-yl)acetonitrile

    58. {1-{1-[3-fluoro-2- (trifluoromethyl) Isonicotinoyl] Piperidin-4- Yl}-3-[4-(7h- Pyrrolo[2,3- D]pyrimidin-4-yl)- 1h-pyrazol-1- Yl]azetidin-3- Yl}acetonitrile

    59. 1-[1-[[3-fluoro-2-(trifluoromethyl)-4-pyridinyl]carbonyl]-4-piperidinyl]-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl]-3-azetidineacetonitrile;itacitinib

    60. 2-(3-(4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-1-(1-(3-fluoro-2-(trifluoromethyl)-isonicotinoyl)piperidin-4-yl)azetidin-3-yl)acetonitrile

    2.4 Create Date
    2011-10-11
    3 Chemical and Physical Properties
    Molecular Weight 553.5 g/mol
    Molecular Formula C26H23F4N9O
    XLogP31.6
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count5
    Exact Mass553.19616904 g/mol
    Monoisotopic Mass553.19616904 g/mol
    Topological Polar Surface Area120 Ų
    Heavy Atom Count40
    Formal Charge0
    Complexity977
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Treatment of acute graft versus host disease

    5 Pharmacology and Biochemistry
    5.1 ATC Code

    L - Antineoplastic and immunomodulating agents

    L04 - Immunosuppressants

    L04A - Immunosuppressants

    L04AA - Selective immunosuppressants

    L04AA46 - Itacitinib