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    Chemistry

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    Also known as: 1310726-60-3, Abt-494, Rinvoq, Upadacitinib anhydrous, 4ra0kn46e0, (3s,4r)-3-ethyl-4-(1,5,7,10-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaen-12-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide
    Molecular Formula
    C17H19F3N6O
    Molecular Weight
    380.4  g/mol
    InChI Key
    WYQFJHHDOKWSHR-MNOVXSKESA-N
    FDA UNII
    4RA0KN46E0
    Upadacitinib
    Upadacitinib is an oral Janus kinase (JAK)1-selective inhibitor and a disease-modifying antirheumatic drug (DMARD) used in the treatment of rheumatoid arthritis to slow down disease progression. Rheumatoid arthritis is a chronic autoimmune inflammatory disease affecting the peripheral joints. It is characterized by synovial inflammation and hyperplasia, autoantibody production, cartilage damage and bone destruction, leading to co-morbidities. Despite a variety of therapeutic agents available for treatment, up to 40% of the patients do not respond to current therapies, including biological therapies. The etiology of the disease is mostly unknown; however, the role of JAK as a driver of immune-mediated conditions was discovered, leading to the use of JAK as therapeutic targets for rheumatoid arthritis. To reduce dose-related toxicity (as seen with some pan-JAK inhibitors) without significantly affecting efficacy, more selective JAK1 inhibitors, upadacitinib and [filgotinib], were developed. The FDA approved Upadacitinib in August 2019 for the treatment of adults with moderately to severely active rheumatoid arthritis who have had an inadequate response or intolerance to methotrexate. In December 2019, it was additionally approved by the European Commission for the same indication in patients with inadequate response or intolerance to one or more DMARDs and can be used as monotherapy or in combination with methotrexate. Upadacitinib is marketed under the brand name RINVOQ for oral administration. It is currently being investigated in several clinical trials assessing its therapeutic effectiveness in other inflammatory diseases, such as psoriatic arthritis, ankylosing spondylitis, ulcerative colitis, and atopic dermatitis.
    1 2D Structure

    Upadacitinib

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3S,4R)-3-ethyl-4-(1,5,7,10-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaen-12-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide
    2.1.2 InChI
    InChI=1S/C17H19F3N6O/c1-2-10-7-25(16(27)24-9-17(18,19)20)8-11(10)13-5-22-14-6-23-15-12(26(13)14)3-4-21-15/h3-6,10-11,21H,2,7-9H2,1H3,(H,24,27)/t10-,11+/m1/s1
    2.1.3 InChI Key
    WYQFJHHDOKWSHR-MNOVXSKESA-N
    2.1.4 Canonical SMILES
    CCC1CN(CC1C2=CN=C3N2C4=C(NC=C4)N=C3)C(=O)NCC(F)(F)F
    2.1.5 Isomeric SMILES
    CC[C@@H]1CN(C[C@@H]1C2=CN=C3N2C4=C(NC=C4)N=C3)C(=O)NCC(F)(F)F
    2.2 Other Identifiers
    2.2.1 UNII
    4RA0KN46E0
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (3s,4r)-3-ethyl-4-(3h-imidazo(1,2-a)pyrrolo(2,3-e)pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)-1-pyrrolidinecarboxamide

    2. Abt-494

    3. Rinvoq

    2.3.2 Depositor-Supplied Synonyms

    1. 1310726-60-3

    2. Abt-494

    3. Rinvoq

    4. Upadacitinib Anhydrous

    5. 4ra0kn46e0

    6. (3s,4r)-3-ethyl-4-(1,5,7,10-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaen-12-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

    7. (3s,4r)-3-ethyl-4-(3h-imidazo(1,2-a)pyrrolo(2,3-e)pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)-1-pyrrolidinecarboxamide

    8. (3s,4r)-3-ethyl-4-(3h-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

    9. 1-pyrrolidinecarboxamide, 3-ethyl-4-(3h-imidazo(1,2-a)pyrrolo(2,3-e)pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)-, (3s,4r)-

    10. Mfcd30502663

    11. Upadacitinib [usan]

    12. Upadacitinib [mi]

    13. Upadacitinib, Abt-494

    14. Upadacitinib (usan/inn)

    15. Upadacitinib [inn]

    16. Upadacitinib [usan:inn]

    17. Upadacitinib (abt-494)

    18. Unii-4ra0kn46e0

    19. Upadacitinib [who-dd]

    20. Gtpl9246

    21. Schembl9991056

    22. Chembl3622821

    23. Abt 494

    24. Dtxsid901027919

    25. Upadacitinib [orange Book]

    26. Amy16528

    27. Bcp19011

    28. Ex-a1628

    29. Bdbm50503287

    30. S8162

    31. Cs-6150

    32. Db15091

    33. Abbv-599 Component Upadacitinib

    34. Abt494;abt-494;abt 494

    35. Ncgc00588874-01

    36. Ac-30326

    37. As-56379

    38. Hy-19569

    39. Upadacitinib Component Of Abbv-599

    40. J3.590.729g

    41. C72237

    42. D10994

    43. Q27074125

    44. (3s,4r)-3-ethyl-4-(3h-imidazo(1,2-a)pyrrolo(2,3-e)pyrazin- 8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide Tyrosine Kinase Inhibitor

    45. (3s,4r)-3-ethyl-4-(3h-imidazo(1,2-a)pyrrolo(2,3-e)pyrazin-8-yl)-n-(2,2,2- Trifluoroethyl)pyrrolidine-1-carboxamide

    46. Rel-(-)-(3s,4r)-3-ethyl-4-(3h-imidazo(1,2-a)pyrrolo(2,3-e)pyrazin-8-yl)-n-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

    2.4 Create Date
    2012-08-19
    3 Chemical and Physical Properties
    Molecular Weight 380.4 g/mol
    Molecular Formula C17H19F3N6O
    XLogP32.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count3
    Exact Mass380.15724374 g/mol
    Monoisotopic Mass380.15724374 g/mol
    Topological Polar Surface Area78.3 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity561
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    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

    Upadacitinib is indicated for the treatment of moderately to severely active rheumatoid arthritis or active psoriatic arthritis in adult patients who have had an inadequate response or intolerance to one or more disease-modifying anti-rheumatic drugs (DMARDs), such as methotrexate or TNF blockers. For these indications, upadacitinib may be used as monotherapy or in combination with methotrexate. Upadacitinib is also indicated for the treatment of active ankylosing spondylitis in adult patients who have an inadequate response to conventional therapy and for the treatment of moderate to severe atopic dermatitis in patients aged 12 years and older who are candidates for systemic therapy. Combining upadacitinib with other JAK inhibitors, biologic DMARDs, or other potent immunosuppressive agents is not recommended.

    FDA Label

    Rheumatoid arthritis

    RINVOQ is indicated for the treatment of moderate to severe active rheumatoid arthritis in adult patients who have responded inadequately to, or who are intolerant to one or more disease-modifying anti-rheumatic drugs (DMARDs). RINVOQ may be used as monotherapy or in combination with methotrexate.

    Psoriatic arthritis

    RINVOQ is indicated for the treatment of active psoriatic arthritis in adult patients who have responded inadequately to, or who are intolerant to one or more DMARDs. RINVOQ may be used as monotherapy or in combination with methotrexate.

    Axial spondyloarthritis

    Non-radiographic axial spondyloarthritis (nr-axSpA)

    RINVOQ is indicated for the treatment of active non-radiographic axial spondyloarthritis in adult patients with objective signs of inflammation as indicated by elevated C-reactive protein (CRP) and/or magnetic resonance imaging (MRI), who have responded inadequately to nonsteroidal anti-inflammatory drugs (NSAIDs).

    Ankylosing spondylitis (AS, radiographic axial spondyloarthritis )

    RINVOQ is indicated for the treatment of active ankylosing spondylitis in adult patients who have responded inadequately to conventional therapy.

    Atopic dermatitis

    RINVOQ is indicated for the treatment of moderate to severe atopic dermatitis in adults and adolescents 12 years and older who are candidates for systemic therapy.

    Ulcerative colitis

    RINVOQ is indicated for the treatment of adult patients with moderately to severely active ulcerative colitis who have had an inadequate response, lost response or were intolerant to either conventional therapy or a biologic agent.

    Treatment of ulcerative colitis

    Treatment of Crohn's disease

    Treatment of vasculitides

    Treatment of vasculitides

    Treatment of atopic dermatitis

    Treatment of chronic idiopathic arthritis (including rheumatoid arthritis , psoriatic arthritis , spondyloarthritis and juvenile idiopathic arthritis )

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Upadacitinib is a DMARD that works by inhibiting the Janus Kinases (JAKs), which are essential downstream cell signalling mediators of pro-inflammatory cytokines. It is believed that these pro-inflammatory cytokines play a role in many autoimmune inflammatory conditions, such as rheumatoid arthritis. In clinical trials, upadacitinib decreased the activity of pro-inflammatory interleukins, transiently increased the levels of lymphocytes, and insignificantly decreased the levels of immunoglobulins from the baseline.

    5.2 MeSH Pharmacological Classification

    Antirheumatic Agents

    Drugs that are used to treat RHEUMATOID ARTHRITIS. (See all compounds classified as Antirheumatic Agents.)

    Janus Kinase Inhibitors

    Agents that inhibit JANUS KINASES. (See all compounds classified as Janus Kinase Inhibitors.)

    5.3 ATC Code

    L04AA

    L - Antineoplastic and immunomodulating agents

    L04 - Immunosuppressants

    L04A - Immunosuppressants

    L04AA - Selective immunosuppressants

    L04AA44 - Upadacitinib

    5.4 Absorption, Distribution and Excretion

    Absorption

    Upadacitinib displays a dose-proportional pharmacokinetic profile over the therapeutic dose range. Following oral administration, the median time to reach Cmax (Tmax) ranges from 2 to 4 hours. The steady-state plasma concentrations of upadacitinib are reached within 4 days following multiple once-daily administrations, with minimal accumulation. Food intake has no clinically relevant effect on the AUC, Cmax, and Cmin of upadacitinib from the extended-release formulation.

    Route of Elimination

    Following administration of a single radio-labelled dose from the immediate-release formulation, approximately 53% of the total dose was excreted in the feces where 38% of the excreted dose was an unchanged parent drug. About 43% of the total dose was excreted in the urine, where 24% of that dose was in the unchanged parent drug form. Approximately 34% of the total dose of upadacitinib dose was excreted as metabolites.

    Volume of Distribution

    The volume of distribution of upadacitinib in a patient with rheumatoid arthritis and a body weight of 74 kg is estimated to be 224 L following oral administration of an extended-release formula. In a pharmacokinetic study consisting of healthy volunteers receiving the extended-release formulation, the steady-state volume of distribution was 294 L. Upadacitinib partitions similarly between plasma and blood cellular components with a blood to plasma ratio of 1.0.

    Clearance

    The apparent oral clearance of upadacitinib in healthy volunteers receiving the extended-release formulation was 53.7 L/h.

    5.5 Metabolism/Metabolites

    Upadacitinib predominantly undergoes CYP3A4-mediated metabolism; however, upadacitinib is a nonsensitive substrate of CYP3A4. It is also metabolized by CYP2D6 to a lesser extent. In a human radio-labelled study, about 79% of the total plasma radioactivity accounted for the parent drug, and about 13% of the total plasma radioactivity accounted for the main metabolite produced from mono-oxidation, followed by glucuronidation. There are no known active metabolites of upadacitinib.

    5.6 Biological Half-Life

    The mean terminal elimination half-life of upadacitinib ranged from 8 to 14 hours following administration of the extended-release formulation. In clinical trials, approximately 90% of upadacitinib in the systemic circulation was eliminated within 24 hours of dosing.

    5.7 Mechanism of Action

    Rheumatoid arthritis (RA) is a chronic autoimmune inflammatory disease that involves the interplay of several mediators, including the immune cells (mainly T- and B-lymphocytes) and pro-inflammatory cytokines, such as the tumour necrosis factor (TNF), transforming growth factor (TGF), and interleukin 6 (IL-6). The Janus Kinase (JAK) family plays an essential role in the normal physiological functions (such as erythropoiesis), but also the signalling of pro-inflammatory cytokines that are implicated in many immune-mediated diseases. The JAK family consists of four isoforms (JAK1, JAK2, JAK3, and Tyrosine Kinase 2) that each interacts with different cytokine receptors and uniquely associates with the intracellular domains of Type I/II cytokine receptors. JAK1 is primarily involved in the signalling transduction pathways of IL-6, IFN and the common -chain cytokines, including IL-2 and IL-15. IL-6 has been closely studied in particular, as it is a major cytokine involved in B- and T-cell differentiation and the acute phase response in inflammation. Upon interaction of cytokines with their cytokine receptors, the JAKs mediate the JAK-STAT signal transduction pathway in response to receptor activation. JAKs are tyrosine kinases that cause phosphorylation of several proteins, including cytokine receptors and JAKs themselves. Phosphorylation of JAKs promotes the phosphorylation and activation of the signalling molecules called STATs, leading to their nuclear translocation, binding to DNA promoters, and target gene transcription. JAK1-mediated signalling pathways ultimately promote pro-inflammatory events, such as increased proliferation and survival of immune cells, T cell differentiation, and macrophage activation. Upadacitinib is a selective JAK1 inhibitor that has a negligible effect on JAK3, leading to an improved drug safety profile. Upadacitinib blocks the cellular processes that contribute to the inflammatory conditions in rheumatoid arthritis. In human leukocytes cellular assays, upadacitinib inhibited JAK1/3-induced phosphorylation of STAT3/5 mediated by IL-6/7.

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    01-Oct-2021
    18-Sep-2024
    KGS
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    Average Price (USD/KGS)

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