Structure via PubChem · Public domain (PubChem)
tofacitinib
Sign in to saveAlso known as CP-690,550, CP-690550, tasocitinib, Xeljanz®
Tofacitinib, sold under the brand Xeljanz, Neojanz among others, is a medication used to treat rheumatoid arthritis, psoriatic arthritis, ankylosing spondylitis, polyarticular-course juvenile idiopathic arthritis, and ulcerative colitis. It is a janus kinase (JAK) inhibitor, discovered and developed by the National Institutes of Health and Pfizer.
Chemical data
- Formula
- C16H20N6O
- Molecular weight
- 312.37 g/mol
- IUPAC name
- 3-[(3R,4R)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile
- SMILES
- C[C@@H]1CCN(C[C@@H]1N(C)C2=NC=NC3=C2C=CN3)C(=O)CC#N
- InChIKey
- UJLAWZDWDVHWOW-YPMHNXCESA-N
- XLogP
- 1.5
- Polar surface area
- 88.9 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2012
- Admin. routes
- oral
- Indications
- rheumatoid arthritis, psoriatic arthritis, ulcerative colitis, alopecia areata
via ChEMBL · EBI
Research
4,497 papers- Tofacitinib as Induction and Maintenance Therapy for Ulcerative Colitis.The New England journal of medicine · 2017
- Tofacitinib for the treatment of ankylosing spondylitis: a phase III, randomised, double-blind, placebo-controlled study.Annals of the rheumatic diseases · 2021
- Tofacitinib experience in patients with enteropathic arthritis.Immunotherapy · 2023
- Tofacitinib for Acute Severe Ulcerative Colitis: A Systematic Review.Journal of Crohn's & colitis · 2023
- Tofacitinib in paediatric dermatoses: a narrative review.Clinical and experimental dermatology · 2022
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 312.17
Show 10 more facts
- chemical formula
- C₁₆H₂₀N₆O
- legal status (medicine)
- boxed warning
- isomeric SMILES
- C[C@@H]1CCN(C[C@@H]1N(C)C2=NC=NC3=C2C=CN3)C(=O)CC#N
- canonical SMILES
- CC1CCN(CC1N(C)C2=NC=NC3=C2C=CN3)C(=O)CC#N
- World Health Organisation international non-proprietary name
- tofacitinib
- subject has role
- protein kinase inhibitors
- defined daily dose
- 10
- medical condition treated
- bald head
- physically interacts with
- Janus kinase 3
- Commons category
- Tofacitinib
Sources (7)
via Wikidata · CC0
~13 min read
Encyclopedic overview
18 sectionsContents
- Medical uses
- Rheumatoid arthritis
- Ulcerative colitis
- Adverse effects
- Mechanism
- History
- Society and culture
- Economics
- Names
- Research
- Psoriasis
- Alopecia areata
- Vitiligo
- Atopic dermatitis
- Ankylosing spondylitis
- Ulcerative colitis
- Epilepsy
- References
{{Drugbox | Watchedfields = changed | verifiedrevid = | image = Tofacitinib.svg | image_class = skin-invert-image | width = | alt = | caption = | pronounce = | tradename = Xeljanz, Neojanz, Jaquinus, Tofacinix, Others | Drugs.com = | MedlinePlus = a613025 | DailyMedID = Tofacitinib | pregnancy_AU = D | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = By mouth | class = Janus kinase (JAK) inhibitor | ATC_prefix = L04 | ATC_suffix = AF01 | ATC_supplemental = | legal_AU = S4 | legal_AU_comment = | legal_BR = | legal_BR_comment = | legal_CA = Rx-only | legal_CA_comment = | legal_DE = | legal_DE_comment = | legal_NZ = | legal_NZ_comment = | legal_UK = POM | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = | legal_EU = Rx-only | legal_EU_comment = | legal_UN = | legal_UN_comment = | legal_status = Rx-only
| bioavailability = 74% | protein_bound = 40% | metabolism = Liver (via CYP3A4 and CYP2C19) | metabolites = | onset = | elimination_half-life = 3 hours | duration_of_action = | excretion = Urine
Excerpted from Wikipedia’s “tofacitinib” article, available under the CC BY-SA 4.0 licence.