Upadacitinib

Upadacitinib
Clinical data
Pronunciation/juˌpædəˈsɪtɪnɪb/
ew-PAD-ə-SI-ti-nib
Trade namesRinvoq
Other namesABT-494
AHFS/Drugs.comMonograph
MedlinePlusa619051
License data
Pregnancy
category
  • AU: D
  • Not recommended
Routes of
administration
By mouth
Drug classJanus kinase (JAK) inhibitor
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding52%
MetabolismLiver (CYP3A major, CYP2D6 minor)
MetabolitesM4, an acyl glucuronide
Elimination half-life9–14 (6–15) hours
ExcretionMainly unchanged in feces (38%) and urine (24%)
Identifiers
  • (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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H19F3N6O
Molar mass380.375 g·mol−1
3D model (JSmol)
  • CC[C@@H]1CN(C(=O)NCC(F)(F)F)C[C@@H]1c1cnc2cnc3[nH]ccc3n12
  • 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 Y
  • Key:WYQFJHHDOKWSHR-MNOVXSKESA-N Y

Upadacitinib, sold under the brand name Rinvoq, is a medication used for the treatment of rheumatoid arthritis, psoriatic arthritis, atopic dermatitis, ulcerative colitis, Crohn's disease, ankylosing spondylitis, and axial spondyloarthritis. Upadacitinib is a Janus kinase (JAK) inhibitor that works by blocking the action of enzymes called Janus kinases. These enzymes are involved in setting up processes that lead to inflammation, and blocking their effect brings inflammation in the joints under control.

Common side effects include upper respiratory tract infections (common cold, sinus infections), nausea, cough, and fever.

Upadacitinib was approved for medical use in both the United States and the European Union in 2019.