Tofacitinib

Tofacitinib
Clinical data
Trade names	Xeljanz, Jaquinus, Tofacinix, Others
Other names	CP-690550
AHFS/Drugs.com	Monograph
MedlinePlus	a613025
License data	US DailyMed: Tofacitinib;
Pregnancy; category	AU: D;
Routes of; administration	By mouth
Drug class	Janus kinase (JAK) inhibitor
ATC code	L04AF01 (WHO) ;
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
Bioavailability	74%
Protein binding	40%
Metabolism	Liver (via CYP3A4 and CYP2C19)
Elimination half-life	3 hours
Excretion	Urine
Identifiers
	IUPAC name 3-[(3R,4R)-4-Methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile;
CAS Number	477600-75-2;
PubChem CID	9926791;
PubChem SID	347827811;
IUPHAR/BPS	5677;
DrugBank	DB08895 ;
ChemSpider	8102425 ;
UNII	87LA6FU830;
KEGG	D09970 ; as salt: D09783 ;
ChEBI	CHEBI:71200 ;
ChEMBL	ChEMBL221959 ;
PDB ligand	MI1 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID90197271 ;
ECHA InfoCard	100.215.928
Chemical and physical data
Formula	C16H20N6O
Molar mass	312.377 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1CCN(C(=O)CC#N)CC1N(C)c1ncnc2[nH]ccc12;
	InChI InChI=1S/C16H20N6O/c1-11-5-8-22(14(23)3-6-17)9-13(11)21(2)16-12-4-7-18-15(12)19-10-20-16/h4,7,10-11,13H,3,5,8-9H2,1-2H3,(H,18,19,20)/t11-,13+/m1/s1; Key:UJLAWZDWDVHWOW-YPMHNXCESA-N;

Tofacitinib, sold under the brand Xeljanz 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.

Common side effects include diarrhea, headache, and high blood pressure. Serious side effects may include infections, cancer, and pulmonary embolism. In 2019, the safety committee of the European Medicines Agency began a review of tofacitinib and recommended that doctors temporarily not prescribe the 10 mg twice-daily dose to people at high risk for pulmonary embolism. The U.S. Food and Drug Administration (FDA) also released warnings about the risk of blood clots. An important side effect of Jakinibs is serious bacterial, mycobacterial, fungal and viral infections. In the phase III trials of tofacitinib among opportunistic infections, pulmonary tuberculosis (TB) was reported in 3 cases all of which were initially negative upon screening for TB.

It was approved for medical use in the United States in November 2012. The extended release version was approved in February 2016. It is available as a generic medication.