Tofacitinib

Structural formula
General
Surname	Tofacitinib
other names	(3 R , 4 R ) -4-methyl-3- (methyl-7 H -pyrrole [2,3- d ] pyrimidin-4-ylamino) -β-oxo-1-piperidinopropane nitrile; 3 - [(3 R , 4 R ) -4-methyl-3- [methyl- (7 H -pyrrole [2,3- d ] pyrimidin-4-yl) amino] piperidin-1-yl] -3-oxopropanenitrile; CP-690550-10; Tasocitinib;
Molecular formula	C 16 H 20 N 6 O (tofacitinib); * C 22 H 28 N 6 O 8 (citrate);
External identifiers / databases
EC number	689-145-4
ECHA InfoCard	100.215.928
PubChem	9926791
DrugBank	DB08895
Wikidata	Q3530324
properties
Molar mass	312.17 g mol −1 (tofacitinib); 504.49 g mol −1 (citrate);
Physical state	solid (citrate)
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tofacitinib (trade name: Xeljanz ; manufacturer: Pfizer Pharma ) is a drug from the group of JAK inhibitors . It is used as a citrate salt . Tofacitinib blocks the Janus kinase JAK1 and JAK3 selectively and irreversibly. As a result, they are no longer able to carry out further activation processes caused by cytokines . One of these processes is the phosphorylation of STAT proteins . Tofacitinib is approved for the treatment of active rheumatoid arthritis and psoriatic arthritis in combination with MTX in adult patients who have had an inadequate response to disease-modifying antirheumatic therapy or who have not tolerated it. It is also approved for the treatment of adult patients with active ulcerative colitis who have responded insufficiently to conventional therapy or a biological agent, no longer responded to it, or who could not tolerate it.

The Safety Committee of the European Medicines Agency (EMA) PRAC decided at its meeting at the end of October 2019 that tofacitinib can increase the risk of blood clots in the lungs and deep venous system in high-risk patients. Therefore, the preparation should be used with caution.

Web links

Rote-Hand- Liefe since March 2019 on Xeljanz® (tofacitinib)

Individual evidence

↑ ^a ^b Data sheet tofacitinib citrate, ≥98% (HPLC) from Sigma-Aldrich , accessed on May 1, 2019 ( PDF ).
↑ External identifiers or database links for tofacitinib citrate : CAS number: 540737-29-9, EC number: 638-826-4, ECHA InfoCard: 100.166.451 , PubChem : 10174505 , ChemSpider : 8350010 , Wikidata : Q27139435 .
^ Tofacitinib. In: Drugs in R&D. Volume 10, number 4, 2010, pp. 271-284, doi : 10.2165 / 11588080-000000000-00000 , PMID 21171673 , PMC 3585773 (free full text).
↑ Meeting highlights from the Pharmacovigilance Risk Assessment Committee (PRAC) October 28-31, 2019 , PM EMA October 31, 2019, accessed November 4, 2019

[Sigma-1] Data sheet tofacitinib citrate, ≥98% (HPLC) from Sigma-Aldrich , accessed on May 1, 2019 ( PDF ).

[2] External identifiers or database links for tofacitinib citrate : CAS number: 540737-29-9, EC number: 638-826-4, ECHA InfoCard: 100.166.451 , PubChem : 10174505 , ChemSpider : 8350010 , Wikidata : Q27139435 .

[3] Tofacitinib. In: Drugs in R&D. Volume 10, number 4, 2010, pp. 271-284, doi : 10.2165 / 11588080-000000000-00000 , PMID 21171673 , PMC 3585773 (free full text).

[4] Meeting highlights from the Pharmacovigilance Risk Assessment Committee (PRAC) October 28-31, 2019 , PM EMA October 31, 2019, accessed November 4, 2019