PZ0017

Sigma-Aldrich

Tofacitinib citrate

≥98% (HPLC)

Synonym(s):
Tasocitinib citrate salt, CP-690550-10, 3-[(3R,4R)-4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile citrate salt, (3R,4R)-4-Methyl-3-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-β-oxo-1-piperidinepropanenitrile citrate salt
Empirical Formula (Hill Notation):
C16H20N6O · C6H8O7
CAS Number:
Molecular Weight:
504.49
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

manufacturer/tradename

Pfizer®

color

white to beige

solubility

DMSO: 5 mg/mL (clear solution; warmed)

originator

Pfizer

storage temp.

room temp

SMILES string

OC(=O)CC(O)(CC(O)=O)C(O)=O.C[C@@H]1CCN(C[C@@H]1N(C)c2ncnc3[nH]ccc23)C(=O)CC#N

InChI

1S/C16H20N6O.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h4,7,10-11,13H,3,5,8-9H2,1-2H3,(H,18,19,20);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t11-,13+;/m1./s1

InChI key

SYIKUFDOYJFGBQ-YLAFAASESA-N

Gene Information

human ... JAK1(3716), JAK2(3717), JAK3(3718), TYK2(7297)

Related Categories

General description

Tofacitinib is a synthetic molecule corresponding to a molecular weight of 312.4 Da and is permeable by transcellular diffusion.

Application

Tofacitinib citrate has been used:
  • as a ligand for human serum albumin in fluorescence quenching, dynamic light scattering (DLS) measurements, differential scanning calorimetry and molecular docking studies
  • as a medium supplement for full depth articular cartilage (FDC) explants to monitor cytokine-induced proteoglycan loss
  • as a Janus kinase inhibitor in MCF7 breast cancer cells

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

Tofacitinib is a potent inhibitor of Janus kinase 3 (JAK3) with some JAK-1 inhibitory activity as well. It blocks downstream STAT signaling resulting in potent inhibition of inflammatory cytokines with resultant immunosuppressive and anti-inflammatory activity. Tofacitinib is being investigated for for several autoimmune disorders including, rheumatoid arthritis, psoriasis and dry eye.

Other Notes

Tofacitinib has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the Tofacitinib probe summary on the Chemical Probes Portal website.
This compound was developed by Pfizer for Kinase Phosphatase Biology research. To learn more about Sigma′s partnership with Pfizer and view other authentic, high-quality Pfizer compounds, visit sigma.com/bsm-pfizer.

To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

Sold for research purposes under agreement from Pfizer Inc.
Pfizer is a registered trademark of Pfizer, Inc.

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Sung Hun Bae et al.
Pharmaceutics, 12(8) (2020-08-06)
Tofacitinib is a Jak inhibitor developed as a treatment for rheumatoid arthritis. Tofacitinib is metabolized mainly through hepatic CYP3A1/2, followed by CYP2C11. Rheumatoid arthritis tends to increase renal toxicity due to drugs used for long-term treatment. In this study, pharmacokinetic...
Soumya S Rajan et al.
Oncogene, 39(10), 2103-2117 (2019-12-06)
Rational new strategies are needed to treat tumors resistant to kinase inhibitors. Mechanistic studies of resistance provide fertile ground for development of new approaches. Cancer drug addiction is a paradoxical resistance phenomenon, well-described in MEK-ERK-driven solid tumors, in which drug-target...
Ji Sang Lee et al.
Pharmaceutics, 11(7) (2019-07-10)
This study investigated the pharmacokinetics of tofacitinib in rats and the effects of first-pass metabolism on tofacitinib pharmacokinetics. Intravenous administration of 5, 10, 20, and 50 mg/kg tofacitinib showed that the dose-normalized area under the plasma concentration-time curve from time...
Phosphoproteome profiling reveals critical role of JAK-STAT signaling in maintaining chemoresistance in breast cancer
Nascimento AS, et al.
Testing, 8(70), 114756-114756 (2017)
Tofacitinib and TPCA-1 exert chondroprotective effects on extracellular matrix turnover in bovine articular cartilage ex vivo
Kjelgaard-Petersen CF, et al.
Biochemical Pharmacology (2018)
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