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PZ0017

Tofacitinib citrate

Name: Tofacitinib citrate
Brand: SIGMA

≥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:

540737-29-9

Molecular Weight:

504.49

UNSPSC Code:

12352200

PubChem Substance ID:

329823686

NACRES:

NA.77

MDL number:

MFCD11616529

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

100

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Properties

Product Name

Tofacitinib citrate, ≥98% (HPLC)

Quality Level

100

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)

Description

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.

pictograms

GHS08,GHS07

signalword

Warning

hcodes

H302,H361fd

pcodes

P202 - P264 - P280 - P301 + P312 - P308 + P313 - P405

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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Articles

Discover Bioactive Small Molecules for Kinase Phosphatase Biology

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)

Dose-Dependent Pharmacokinetics of Tofacitinib in Rats: Influence of Hepatic and Intestinal First-Pass Metabolism.

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)

View All Related Papers

Global Trade Item Number

SKU	GTIN
PZ0017-5MG	04061833220191
PZ0017-25MG	04061833220184