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PZ0017

Sigma-Aldrich

Tofacitinib citrate

≥98% (HPLC), powder, JAK3 inhibitor

Synonym(s):

(3R,4R)-4-Methyl-3-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-β-oxo-1-piperidinepropanenitrile citrate salt, 3-[(3R,4R)-4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]-3-oxopropanenitrile citrate salt, CP-690550-10, Tasocitinib citrate salt

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About This Item

Empirical Formula (Hill Notation):
C16H20N6O · C6H8O7
CAS Number:
Molecular Weight:
504.49
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

product name

Tofacitinib citrate, ≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

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

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

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

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.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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.

pictograms

Health hazardExclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Usir S Younis et al.
AAPS PharmSciTech, 20(5), 167-167 (2019-04-18)
Preformulation studies on tofacitinib citrate, a small molecule JAK3 specific inhibitor, have not been previously reported in literature. We therefore conducted several preformulation studies on tofacitinib citrate, and its free base, to better understand factors that affect its solubility, stability
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
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
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)

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