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Upadacitinib tartrate

Names

[ CAS No. ]:
1607431-21-9

[ Name ]:
Upadacitinib tartrate

[Synonym ]:
Upadacitinib tartrate
(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 (2R,3R)-2,3-dihydroxybutanedioate, tetrahydrate
(2R,3R)-2,3-Dihydroxysuccinic acid - (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)-1-pyrrolidinecarboxamide hydrate (1:1:4)
Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-, compd. with (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)-1-pyrrolidinecarboxamide, hydrate (1:1:4)
ABT-494
UNII-7KCW9IQM02

Biological Activity

[Description]:

Upadacitinib (ABT-494) tartrate tetrahydrate is a potent, orally active and selective Janus kinase 1 (JAK1) inhibitor (IC50=43 nM). Upadacitinib tartrate tetrahydrate displays approximately 74 fold selective for JAK1 over JAK2 (200 nM) in cellular assays dependent on specific, relevant cytokines. Upadacitinib tartrate tetrahydrate can be used for several autoimmune disorders research[1][2].

[Related Catalog]:

Signaling Pathways >> JAK/STAT Signaling >> JAK
Signaling Pathways >> Epigenetics >> JAK
Signaling Pathways >> Stem Cell/Wnt >> JAK
Research Areas >> Inflammation/Immunology

[Target]

JAK1:0.043 μM (IC50)

JAK2:0.2 μM (IC50)

JAK3:2.3 μM (IC50)

Tyk2:4.7 μM (IC50)


[In Vitro]

In biochemical assays, Upadacitinib tartrate tetrahydrate is 74-fold more selective for JAK-1 than for JAK-2 (which is involved in erythropoiesis) and 58-fold more selective for JAK-1 than for JAK-3 (which is involved in immunosurveillance)[1].

[In Vivo]

Upadacitinib (0.1-10 mg/kg; oral gavage; twice a day for 10 days) tartrate tetrahydrate demonstrates efficacy in rat arthritis models[3]. Animal Model: Female Lewis rats (Rat adjuvant-induced arthritis model)[3] Dosage: 0.1, 0.3, 1, 3, 10 mg/kg Administration: Oral gavage; twice a day for 10 days Result: Inhibited disease pathology in rat adjuvant induced arthritis.

[References]

[1]. Nakayamada S, et al. Recent Progress in JAK Inhibitors for the Treatment of Rheumatoid Arthritis. BioDrugs. 2016 Oct;30(5):407-419.

[2]. J. Voss, et al. THU0127 Pharmacodynamics of A Novel JAK1 Selective Inhibitor in Rat Arthritis and Anemia Models and in Healthy Human Subjects. doi 10.1136/annrheumdis-2014-eular.3823.

[3]. Parmentier JM, et al. In vitro and in vivo characterization of the JAK1 selectivity of upadacitinib (ABT-494). BMC Rheumatol. 2018 Aug 28;2:23.

Chemical & Physical Properties

[ Molecular Formula ]:
C21H33F3N6O11

[ Molecular Weight ]:
602.516

[ Exact Mass ]:
602.215942

Related Compounds