Structure via PubChem · Public domain (PubChem)
upadacitinib
Sign in to saveAlso known as upadacitinib (proposed INN)
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.
Key facts
- Drug.image
- Upadacitinib.svg
- Drug.image_class
- skin-invert-image
- Drug.tradename
- Rinvoq
- Drug.MedlinePlus
- a619051
- Drug.licence_EU
- yes
- Drug.DailyMedID
- Upadacitinib
- Drug.pregnancy_AU
- D
- Drug.pregnancy_category
- Not recommended
- Drug.routes_of_administration
- By mouth
- Drug.class
- Janus kinase (JAK) inhibitor
- Drug.ATC_prefix
- L04
- Drug.ATC_suffix
- AF03
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.legal_EU
- Rx-only
- Drug.legal_status
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C17H19F3N6O
- Molecular weight
- 380.4 g/mol
- 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
- SMILES
- CC[C@@H]1CN(C[C@@H]1C2=CN=C3N2C4=C(NC=C4)N=C3)C(=O)NCC(F)(F)F
- InChIKey
- WYQFJHHDOKWSHR-MNOVXSKESA-N
- XLogP
- 2.7
- Polar surface area
- 78.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2019
- Admin. routes
- oral
- Indications
- atopic eczema, Crohn's disease, ulcerative colitis, psoriatic arthritis
via ChEMBL · EBI
Research
2,118 papers- Upadacitinib Induction and Maintenance Therapy for Crohn's Disease.The New England journal of medicine · 2023
- Efficacy and Safety of Upadacitinib vs Dupilumab in Adults With Moderate-to-Severe Atopic Dermatitis: A Randomized Clinical Trial.JAMA dermatology · 2021
- A Phase 3 Trial of Upadacitinib for Giant-Cell Arteritis.The New England journal of medicine · 2025
- Upadacitinib: Mechanism of action, clinical, and translational science.Clinical and translational science · 2024
- Trial of Upadacitinib and Adalimumab for Psoriatic Arthritis.The New England journal of medicine · 2021
via PubMed
Wikidata facts
- Subclass of
- Janus kinase inhibitors
- Mass
- 380.157244
Show 5 more facts
- chemical formula
- C₁₇H₁₉F₃N₆O
- legal status (medicine)
- boxed warning
- canonical SMILES
- CCC1CN(CC1C2=CN=C3N2C4=C(NC=C4)N=C3)C(=O)NCC(F)(F)F
- isomeric SMILES
- CC[C@@H]1CN(C[C@@H]1C2=CN=C3N2C4=C(NC=C4)N=C3)C(=O)NCC(F)(F)F
- subject has role
- protein kinase inhibitors
via Wikidata · CC0
~17 min read
Encyclopedic overview
18 sectionsContents
- Medical uses
- Contraindications
- Interactions
- Side effects
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- History
- Clinical trials
- Phase I studies
- Phase II studies
- BALANCE I
- BALANCE II
- CELEST
- Phase III studies
- SELECT-COMPARE
- SELECT-CHOICE
- References
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.
Excerpted from Wikipedia’s “upadacitinib” article, available under the CC BY-SA 4.0 licence.