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About This Item
Empirical Formula (Hill Notation):
C16H20N6O · C6H8O7
CAS Number:
Molecular Weight:
504.49
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
Tofacitinib citrate, ≥98% (HPLC)
Quality Level
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
human ... JAK1(3716), JAK2(3717), JAK3(3718), TYK2(7297)
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.
Tofacitinib is a potent inhibitor of Janus kinase 3 (JAK3).
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Repr. 2
Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
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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)
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
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)

